Home Vacation Home Rentals By Owner In Siesta Key, FL

Showing 220 Of 517 Vacation Rentals
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$322.03

/ Nightly
Private Vacation Home

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. The Tortuga Bungalow features a bright and airy one bedroom space; with a kitchen, bathroom, and a private lanai overlooking Heron Lagoon. With a king-size bed you`ll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. The sofa turns into a queen size bed, allowing for a max occupancy of three.brbrWe are happy to provide free high-speed WiFi internet & HDTV equipped with live sports & extensive channel options via complementary DirecTV Stream, also included are electric appliances so you will not miss a beat. You have your own private lanai, great for lounging or grilling. Take a few steps further and you can enjoy the dock on Heron Lagoon. The resort`s private dock allows for lounging, fishing, or even launching one of our complementary kayaks!brbrIn addition to Heron Lagoon access, this resort has a shared, heated pool and outdoor space that is perfect to bask in the Florida sun! The pool is surrounded by an array of palm trees, Florida`s famous mangroves and tropical plants, providing a beautiful backsplash of greenery and partial shade. On the pool deck, you’ll find numerous sun-loungers to get your tan in, hang-out with friends and family, or just relax :)brbrAdjacent to the pool deck, you can walk out on the shared patio with multiple BBQ-Grills and covered outdoor dining tables. This outdoor space is perfect for a pool fun & grill-outs!brbrResort guests will have access to the heated pool, patio with sun loungers, the dock on Heron Lagoon, kayaks, the courtyard for outdoor eating and grilling, ONE-free-parking (one vehicle max), and a `beach-load-out` that includes beach towels, chairs, cooler, a beach blanket, cart and an umbrella. The laundry facilities are free and shared with other guests. The Tortuga`s lanai and the entire interior of your bungalow is exclusive to you!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches in Siesta Key. Unplug and explore your surroundings, such as Turtle Beach 1-mile south from this location or Crescent Beach, just 2.5 miles north.brbrSporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. From cafes to fine dining in the area to the beautiful Siesta Key beaches, you will certainly find what you need. Did we mention that we provide all guests a complementary ‘beach-loud-out’ that includes beach towels, chairs, blanket, cart, cooler and an umbrella.brbrYou will receive ONE free parking spot on-site, thus if you’re looking to soak up the sun and tour the island in your own vehicle, you always have an easy place to park when you come back. If you don’t want to drive, take advantage of the free Siesta Key Breeze Trolley which stops right outside our parking lot every 20 minutes from 8AM-10PM daily. Siesta Key Dreams is also happy to offer free baggage-drop off to make your travels easier. We also provide on-site golf-cart rental! brbrNote: One parking space per unit, no additional parking.brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement and guest verification, this allows us to provide a safe space and contactless check-in.brbrDo you have a large party Siesta Key Dreams offers 3-bungalow rentals or you can even rent the entire resort!brbrPayment: 50% at time of reservation, 50% 2-days prior to arrivalbrCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM- 7AM brPool Hours: 7AM - 9PMbrNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key DreamsbrPets: No PetsbrParking: One reserved parking space (1 vehicle max)brAdditional Details: See Vacation Rental Agreement for all details
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Exceptional(24)

$451.09

/ Nightly
Private Vacation Home

Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music!

Siesta Key, Florida, United States

Kaia's Sun and SeabrNewly remodeled with pool and jacuzzi, just 1-minute walk to Siesta Key beach! Poolside lounging and grilling, sunsets, sandbars, and on reef snorkeling and paddling. Just 4-min walk to shopping dining bars and live music. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Front Porch – southwesterly porch on the palms (shared)br∙ Beaches – 1-min walk to award winning beaches, white sand, calm waterbr∙ Relaxing – private balcony and patio with dining and loungingbr∙ Pool – beautiful heated pool with tropical plants just 1-minute walkbr∙ Reef Snorkeling – 70-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –1-minute walk to best sunsets and whatever comes nextbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbrbrThe BeachbrAccess to two private Siesta Key beaches. With no public parking nearby, this cove is one of Siesta's more exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 4-minutes two 12 bars and restaurants. Walk 7-minutes to Siesta's top eco-adventures boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe at the beach, nap by the pool or enjoy Siesta s top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise now add one of the Gulf Coasts best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrThis unit is two flights up with no one above it. There is a king bedroom, a queen bedroom and a sectional sofa. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels and the resort supplies chairs and umbrellas. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.
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Exceptional(44)

$676.28

/ Nightly
Private Vacation Home

Steps from Beach. Roof Top Deck-Gulf Views. Shared Heated Pool

Siesta Key, Florida, United States

Siesta Sun by Siesta Key Luxury Rental Properties is a stunning 3 bedroom, 3. and a half bath Siesta Key luxury rental located just a 1-minute walk to Siesta Key Beach. This elevated duplex offers beach views, a private rooftop deck with sweeping Gulf scenery, and a bright coastal interior perfect for extended stays, family vacations, and groups seeking refined yet relaxed island living. With access to a shared tropical pool, a lively game room, and pet friendly accommodations. Siesta Sun delivers effortless coastal comfort near Crescent Beach, island restaurants, and the Siesta Key Breeze Trolley. brbrHighlights br• 1-minute walk to Siesta Key Beach br• Beach views and rooftop deck br• 3 Bedrooms / 3.5 Bathrooms br• 3 Kings and Daybed with Twin Trundle br• Screened dining area and BBQ grill br• Shared tropical pool br• Game room with foosball and bar seating br• Dog friendly (with approval) br• Washer and dryer in unit br• 3 parking spaces brbrWake up to island sunshine and head up to your private rooftop deck, where lounge chairs and panoramic Gulf views set the tone for a perfect Siesta Key morning. The shared backyard features a sparkling pool surrounded by tropical landscaping and plenty of comfortable seating, ideal for afternoons between beach visits. You’ll also enjoy a screened dining balcony with a BBQ grill, perfect for easy outdoor meals. The downstairs game room adds a fun, casual hangout option with foosball, bar seating, and a refrigerator for drinks and snacks. brbrInside, a spacious open concept layout pairs coastal style with comfort. The living room offers plush sofas, a large TV, and built in shelving that adds charm and character. The kitchen is fully equipped with stainless steel appliances, ample counter space, bar seating, and cookware. The dining area seats eight and opens seamlessly to the screened balcony, creating an inviting indoor-outdoor flow that complements the island lifestyle. brbrThe primary bedroom features a king bed, TV, coastal decor, and access to the balcony. Its ensuite bathroom includes a double vanity, a beautifully tiled walk-in shower, and a large walk-in closet. The second bedroom also includes a king bed, balcony access, and a private ensuite bathroom with a shower and tub combination. The third bedroom offers a king bed, TV, and access to the hallway bathroom with a shower/tub combination. On the way to the rooftop deck, a cozy den includes a daybed with a twin trundle, providing additional sleeping space. brbrRoom Details br-Primary Bedroom (2nd floor): King bed, balcony, ensuite bathroom with walk-in shower br-Second Bedroom (2nd floor): King bed, balcony, ensuite bathroom with shower/tub combo br-Third Bedroom (2nd floor): King bed br-Den (3rd floor): Daybed with Twin Trundle and rooftop access brbrThis home includes a rooftop deck, screened dining area, BBQ grill, shared pool, lounge seating, balconies, washer and dryer, and three parking spaces. Located along Beach Road and just steps from the Gulf, Siesta Sun offers unbeatable walkability to shops, island eateries, Crescent Beach, and the Siesta Key Breeze Trolley. Larger groups can reserve the neighboring duplex, Island Sun, for a combined six-bedroom coastal retreat. brbrSiesta Sun by Siesta Key Luxury Rental Properties blends elevated coastal design with unbeatable proximity to the beach. From Gulf view rooftop sunsets to relaxing poolside days, this home offers everything you need for a memorable Siesta Key escape. Book your stay at Siesta Sun today and experience the best of Siesta Key! brbr- brThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
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Exceptional(1)

$243.85

/ Nightly
Private Vacation Home

Beautiful Four Bedroom, Three Bathroom Home in Siesta Key

Siesta Key, Florida, United States

Coastal Luxury Retreat in Siesta Key – Spacious 4BR Home with Private Pool brbrWelcome to your perfect Siesta Key getaway! This stunning 4-bedroom, 3-bathroom coastal retreat combines modern luxury with relaxed island living. Thoughtfully designed for comfort and style, this home offers plenty of space for families or groups seeking a serene, upscale escape — available for monthly rentals only.brbrInside the Home:brStep into a bright, open-concept living area filled with natural light and chic, modern décor. The fully equipped gourmet kitchen features sleek appliances, a large island, and everything you need to cook and entertain in style. The spacious living and dining areas flow seamlessly, creating the perfect setting for gathering and relaxation.brbrBedrooms & Baths:brMaster Suite: King bed, ensuite bathroom, and direct access to the pool area.brGuest Bedroom 1: King bed with stylish furnishings and plenty of storage.brGuest Bedroom 2: King bed and modern coastal accents.brGuest Bedroom 3: Full-over-twin bunk bed — perfect for kids or extra guests.brbrOutdoor Living:brEnjoy your own private heated pool surrounded by lush tropical landscaping. Lounge under the sun, dine al fresco on the patio, or unwind with an evening swim under the stars — your personal oasis awaits!brbrLocation:brSituated in one of Siesta Key's most desirable neighborhoods, you'll be just minutes from Siesta Key Village with its charming shops, restaurants, and nightlife — and, of course, the world-famous Siesta Beach with its powdery white sand.brbrWhether you're spending a day at the beach or staying at the house, we have you covered. Just load up the beach chairs, coolers, and umbrella plus wagon for transport or use the available bikes to head over for a walk or time in the village. If you feel like a day at home there is a great swimming pool, or lounge in the spa. Maybe you'll try your hand at billiards or convert it to the ping pong table in the games room located in the pool cabana. It's a great place for watching the game or sending your kids out to play. Fun day or night, as the seating area adjacent to the cabana is great for star watching under the live oaks. Plus your dog will be safe in the fully fenced yard, complete with outdoor seating, perfect for exterior ambiance. There also is a little clubhouse shed thats at the rear of the property, full equipped with TV, wifi, and a pool table for some fun and games outside the main house.brbr​​​​​​​Highlights:brPrivate pool & outdoor lounge areabrModern, fully furnished interiorsbrWasher & dryerbrHigh-speed Wi-Fi & smart TVsbrAmple parkingbrMonthly rentals onlybrWhether you're seeking a peaceful retreat or an extended tropical escape, this Siesta Key gem delivers the perfect balance of comfort, style, and location.
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Bath 3

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Sleep 8

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Exceptional(1)

$311.86

/ Nightly
Private Vacation Home

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. The Ringling Bungalow features a bright and airy one bedroom space; with a kitchen, bathroom, and a private deck overlooking Heron Lagoon. With a king-size bed you`ll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. The sofa turns into a queen size bed, allowing for a max occupancy of three.brbrWe are happy to provide free high-speed WiFi internet & HDTV equipped with live sports & extensive channel options via complementary DirecTV, also included are electric appliances so you will not miss a beat. You have your own private deck, great for lounging or grilling. Take a few steps further and you can enjoy the private dock on Heron Lagoon. The resort`s private dock allows for lounging, fishing, or even launching one of our complementary kayaks!brbrIn addition to Heron Lagoon access, this resort has a shared, heated pool and outdoor space that is perfect to bask in the Florida sun! The pool is surrounded by an array of palm trees, Florida`s famous mangroves and tropical plants, providing a beautiful backsplash of greenery and partial shade. On the pool deck, you’ll find numerous sun-loungers to get your tan in, hang-out with friends and family, or just relax :)brbrAdjacent to the pool deck, you can walk out on the shared patio with multiple BBQ-Grills and covered outdoor dining tables. This outdoor space is perfect for a pool fun & grill-outs!brbrResort guests will have access to the heated pool, patio with sun loungers, the dock on Heron Lagoon, kayaks, the courtyard for outdoor eating and grilling, ONE-free-parking (one vehicle max), and a `beach-load-out` that includes beach towels, chairs, cooler, a beach blanket, cart and an umbrella. The laundry facilities are free and shared with other guests. The Ringling Bungalow`s deck overlooking Heron Lagoon and the entire interior of your bungalow is exclusive to you!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches in Siesta Key. Unplug and explore your surroundings, such as Turtle Beach 1mile south from this location or Crescent Beach, just 2.5 miles north.brbrSporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. From cafes to fine dining in the area to the beautiful Siesta Key beaches, you will certainly find what you need. Did we mention that we provide all guests a complementary ‘beach-loud-out’ that includes beach towels, chairs, blanket, cart, cooler and an umbrella.brbrYou will receive ONE free parking spot on-site, thus if you’re looking to soak up the sun and tour the island in your own vehicle, you always have an easy place to park when you come back. If you don’t want to drive, take advantage of the free Siesta Key Breeze Trolley which stops right outside our parking lot every 20 minutes from 8AM-10PM daily. Siesta Key Dreams is also happy to offer free baggage-drop off to make your travels easier. We also provide on-site golf-cart rental! brbrNote: One parking space per unit, no additional parking.brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement and guest verification, this allows us to provide a safe space and contactless check-in.brbrDo you have a large party Siesta Key Dreams offers 3-bungalow rentals or you can even rent the entire resort!brbrPayment: 50% at time of reservation, 50% 7-days prior to arrivalbrCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM- 7AM brPool Hours: 7AM - 9PMbrNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key DreamsbrPets: No PetsbrParking: One reserved parking space (1 vehicle max)brAdditional Details: See Vacation Rental Agreement for all details
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$263.32

/ Nightly
Private Vacation Home

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, & kayaks hitched to the private dock on Heron Lagoon. Truly a resort with something for everyone!brbrThe Coconut Bungalow`s one bedroom space; has an open floor plan connecting a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. The Coconut is fully stocked with linens, care essentials, plus eating & cooking utensils. An additional queen size bed pulls out from the sofa in the living room, allowing for a max unit capacity of three.brbrWe are happy to provide free high-speed WiFi internet & DirecTV with live sports, movie channels, and extensive channel options. Also, included are electric appliances so you will not miss a beat. Along with private interior space, you have your own backyard patio. Take a few steps further and you can enjoy the resort`s exclusive dock on Heron Lagoon. The resort`s dock allows for lounging, fishing, or even launching one of our complementary kayaks! brbrIn addition to Heron Lagoon access, this resort has a shared, heated pool and outdoor space that is perfect to bask in the Florida sun! The pool is surrounded by an array of palm trees, Florida`s famous mangroves and tropical plants, providing a beautiful backsplash of greenery and partial shade. On the pool deck, you’ll find numerous sun-loungers to get your tan in, hang-out with friends and family, or just relax :)brbrAdjacent to the pool deck, you can walk out on the shared patio with multiple BBQ-Grills and covered outdoor dining tables. This outdoor space is perfect for a pool gathering & grill-out!brbrResort guests will have access to the heated pool, patio with sun-loungers, the dock on Heron Lagoon, kayaks, the courtyard for outdoor eating and grilling, ONE free-parking space (1 vehicle max), and a `beach-load-out` that includes beach towels, chairs, cooler, blanket, cart and an umbrella. The laundry facilities are free and shared with other guests. The Coconut Bungalow`s backyard patio and the entire interior of your bungalow is exclusive to you!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches in Siesta Key. Unplug and explore your surroundings, such as Turtle Beach, one mile south from this location or Crescent Beach, just 2.5 miles north. Sporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. From cafes to fine dining in the area to the beautiful Siesta Key beaches, you will certainly find what you need.brbrDid we mention that we provide all guests a complementary ‘beach-loud-out’ that includes beach towels, chairs, blanket, cart, cooler and an umbrella.brbrYou will receive ONE free parking spot on-site(one vehicle max), thus if you’re looking to soak up the sun and tour the island in your own vehicle, you always have an easy place to park when you come back. If you don’t want to drive, take advantage of the free Siesta Key Breeze Trolley which stops right outside our parking lot every 20 minutes from 8AM - 10PM daily. Siesta Key Dreams is also happy to offer free baggage-drop off to make your travels easier.brbrIncluded with your reservation are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrella, blanket, cooler and a cart to transport your items easily! Traveling with your children We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request! brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement and guest verification instructions, this allows us to provide a safe space and contactless check-in.brbrDo you have a large party Siesta Key Dreams offers 3-bungalow rentals or you rent the entire resort!brCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM - 7AM brPool Hours: 7AM - 10PMbrParking: 1 reserved parking space (one vehicle max)brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key DreamsbrPets: No PetsbrAdditional Details: See Vacation Rental Agreement for all details
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$247.43

/ Nightly
Private Vacation Home

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, & kayaks hitched to the private dock on Heron Lagoon. Truly a resort with something for everyone!brbrThe Dolphin Bungalow`s one bedroom space; has an open floor plan connecting a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. The Dolphin is fully stocked with linens, care essentials, plus eating & cooking utensils. An additional queen size bed pulls out from the sofa in the living room, allowing for a max unit capacity of three.brbrWe are happy to provide free high-speed WiFi internet & DirecTV with live sports, movie channels, and extensive channel options. Also, included are electric appliances so you will not miss a beat. Along with private interior space, you have your own backyard patio. Take a few steps further and you can enjoy the resort`s exclusive dock on Heron Lagoon. The resort`s dock allows for lounging, fishing, or even launching one of our complementary kayaks! brbrIn addition to Heron Lagoon access, this resort has a shared, heated pool and outdoor space that is perfect to bask in the Florida sun! The pool is surrounded by an array of palm trees, Florida`s famous mangroves and tropical plants, providing a beautiful backsplash of greenery and partial shade. On the pool deck, you’ll find numerous sun-loungers to get your tan in, hang-out with friends and family, or just relax :)brbrAdjacent to the pool deck, you can walk out on the shared patio with multiple BBQ-Grills and covered outdoor dining tables. This outdoor space is perfect for a pool gathering & grill-out!brbrResort guests will have access to the heated pool, patio with sun-loungers, the dock on Heron Lagoon, kayaks, the courtyard for outdoor eating and grilling, ONE free-parking space (1 vehicle max), and a `beach-load-out` that includes beach towels, chairs, cooler, blanket, cart and an umbrella. The laundry facilities are free and shared with other guests. The Dolphin Bungalow`s backyard patio and the entire interior of your bungalow is exclusive to you!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches in Siesta Key. Unplug and explore your surroundings, such as Turtle Beach, one mile south from this location or Crescent Beach, just 2.5 miles north. Sporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. From cafes to fine dining in the area to the beautiful Siesta Key beaches, you will certainly find what you need.brbrDid we mention that we provide all guests a complementary ‘beach-loud-out’ that includes beach towels, chairs, blanket, cart, cooler and an umbrella.brbrYou will receive ONE free parking spot on-site(one vehicle max), thus if you’re looking to soak up the sun and tour the island in your own vehicle, you always have an easy place to park when you come back. If you don’t want to drive, take advantage of the free Siesta Key Breeze Trolley which stops right outside our parking lot every 20 minutes from 8AM - 10PM daily. Siesta Key Dreams is also happy to offer free baggage-drop off to make your travels easier.brbrIncluded with your reservation are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrella, blanket, cooler and a cart to transport your items easily! Traveling with your children We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request! brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement and guest verification instructions, this allows us to provide a safe space and contactless check-in.brbrDo you have a large party Siesta Key Dreams offers 3-bungalow rentals or you rent the entire resort!brCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM - 7AM brPool Hours: 7AM - 10PMbrParking: 1 reserved parking space (one vehicle max)brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key DreamsbrPets: No PetsbrAdditional Details: See Vacation Rental Agreement for all details
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$247.46

/ Nightly
Private Vacation Home

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

The Siesta Key Bungalows offer a heated pool, courtyard & a dock on Heron Lagoon. A resort with something for everyone. The Pineapple Bungalow`s one bedroom space; has an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed, bathroom and front patio, you`ll feel at home. The Pineapple is fully stocked with linens, care essentials, plus eating & cooking utensils. An additional queen size bed pulls out from the sofa in the living room.brbrWe are happy to provide free high-speed WiFi internet & DirecTV with live sports, movie channels, and extensive channel options. Also included are electric appliances so you will not miss a beat. You have your own front patio for lounging. Take a few steps further and you can enjoy resort exclusive dock on Heron Lagoon. The resort`s dock allows for lounging, fishing, or even launching one of our complementary kayaks! brbrIn addition to Heron Lagoon access, this resort has a shared, heated pool and outdoor space that is perfect to bask in the Florida sun! The pool is surrounded by an array of palm trees, Florida`s famous mangroves and tropical plants, providing a beautiful backsplash of greenery and partial shade. On the pool deck, you’ll find numerous sun-loungers to get your tan in, hang-out with friends and family, or just relax :)brbrAdjacent to the pool deck, you can walk out on the shared patio with multiple BBQ-Grills and covered outdoor dining tables. This outdoor space is perfect for a pool gathering & grill-out!brbrResort guests will have access to the heated pool, patio with sun-loungers, the dock on Heron Lagoon, kayaks, the courtyard for outdoor eating and grilling, ONE free-parking space (1 vehicle max), and a `beach-load-out` that includes beach towels, chairs, cooler, blanket, cart and an umbrella. The laundry facilities are free and shared with other guests. The Pineapple Bungalow`s patio and the entire interior of your bungalow is exclusive to you!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches in Siesta Key. Unplug and explore your surroundings, such as Turtle Beach one mile south from this location or Crescent Beach, just 2.5 miles north. Sporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. From cafes to fine dining in the area to the beautiful Siesta Key beaches, you will certainly find what you need.brbrDid we mention that we provide all guests a complementary ‘beach-loud-out’ that includes beach towels, chairs, blanket, cart, cooler and an umbrella.brbrYou will receive ONE free parking spot on-site(one vehicle max), thus if you’re looking to soak up the sun and tour the island in your own vehicle, you always have an easy place to park when you come back. If you don’t want to drive, take advantage of the free Siesta Key Breeze Trolley which stops right outside our parking lot every 20 minutes from 8AM - 10PM daily. Siesta Key Dreams is also happy to offer free baggage-drop off to make your travels easier.brbrIncluded with your reservation are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrella, blanket, cooler and a cart to transport your items easily! Traveling with your children We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request! brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement and guest verification, this allows us to provide a safe space and contactless check-in.brbrDo you have a large party Siesta Key Dreams offers 3-bungalow rentals or you rent the entire resort!brbrPayment: 50% at time of booking, 50% 7-days prior to arrivalbrCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM - 7AM brPool Hours: 7AM - 10PMbrParking: 1 reserved parking space (one vehicle max)brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key DreamsbrPets: No PetsbrAdditional Details: See Vacation Rental Agreement for all details
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$253.08

/ Nightly
Private Vacation Home

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. The Coquina Bungalow features a bright and airy one bedroom space; with a large living room, full-kitchen & a private patio. With a king-size bed and private bathroom you`ll feel at home. The Coquina Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. The living room has a sofa that turns into a queen size bed, allowing for a max unit occupancy of three.brbrWe are happy to provide free high-speed WiFi internet, HDTV equipped with live sports & extensive channel options via DirecTV, also included are electric appliances so you will not miss a beat.brbrJust a few steps through the resort grounds, and you can enjoy the private dock on Heron Lagoon. The resort`s private dock allows for lounging, fishing, or even launching one of our complementary kayaks! In addition to Heron Lagoon access, this resort has a shared-heated-pool and outdoor space that is perfect to bask in the Florida sun! The pool is surrounded by an array of palm trees, Florida`s famous mangroves, and tropical plants, providing a beautiful backsplash of greenery and partial shade. On the pool deck, you’ll find numerous sun-loungers to get your tan in, hang-out with friends and family, or just relax :)brbrAdjacent to the pool deck, you can walk out on the shared patio with multiple BBQ-Grills and covered outdoor dining tables. This outdoor space is perfect for a pool fun & grill-outs!brbrResort guests will have access to the heated pool, patio with sun loungers, the dock on Heron Lagoon, kayaks, the courtyard for outdoor eating and grilling, ONE-free-parking-space (one vehicle max), and a `beach-load-out` that includes beach towels, chairs, cooler, blanket, cart and an umbrella. The laundry facilities are free and shared with other guests. The the entire interior of your Coquina Bungalow and it`s patio is exclusive to you!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches in Siesta Key. Unplug and explore your surroundings, such as Turtle Beach which is 1 mile south from this location or Crescent Beach, just 2.5 miles north.brbrSporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. From cafes to fine dining in the area to beautiful Siesta Key beaches, you will certainly find what you need.brbrDid we mention that we provide all guests a complementary ‘beach-loud-out’ that includes beach towels, chairs, blanket, cart, cooler and an umbrella :)brbrYou will receive ONE-free parking spot on-site, thus if you’re looking to soak up the sun and tour the island in your own vehicle, you always have an easy place to park when you come back. If you don’t want to drive, take advantage of the free Siesta Key Breeze Trolley which stops right outside our parking lot every 20 minutes from 8AM-10PM daily. Siesta Key Dreams is also happy to offer free baggage-drop off to make your travels easier. We also have onsite golf-cart rental available for our guests!brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement and guest verification, this allows us to provide a safe space and contactless check-in.brbrDo you have a large party Siesta Key Dreams offers 3-bungalow rentals or you can even rent the entire resort!brCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10pm - 7AM brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams (entire building rentals are available)brPets: No petsbrAdditional Details: See Vacation Rental Agreement for all details
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Exceptional(1)

$253.15

/ Nightly
Private Vacation Home

Heated Pool, Dock, Kayaks, Turtle Beach 1-mile & Crescent Beach 2-miles, 1-bdr

Siesta Key, Florida, United States

The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, & kayaks hitched to the private dock on Heron Lagoon. Truly a resort with something for everyone!brbrThe Hibiscus Bungalow`s one bedroom space; has a welcoming living room, full-kitchen, and veranda. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. The Hibiscus is fully stocked with linens, care essentials, plus eating & cooking utensils. An additional queen size bed pulls out from the sofa in the living room, allowing for a max unit capacity of three. The Hibiscus is at the end of the building, thus there is only one shared wall.brbrWe are happy to provide free high-speed WiFi internet & DirecTV Stream with live sports, movie channels, and extensive channel options. Also, included is a toaster, microwave, Keurig, drip-coffee machine, ice-maker, blender, oven, stove, fridge, and freezer. brbrAlong with private interior space, you have your own veranda. Take a few steps further and you can enjoy the resort`s exclusive dock on Heron Lagoon. The resort`s dock allows for lounging, fishing, or even launching one of our complementary kayaks! brbrIn addition to Heron Lagoon access, this resort has a shared, heated pool and outdoor space that is perfect to bask in the Florida sun! The pool is surrounded by an array of palm trees, Florida`s famous mangroves and tropical plants, providing a beautiful backsplash of greenery and partial shade. On the pool deck, you’ll find numerous sun-loungers to get your tan in, hang-out with friends and family, or just relax :)brbrAdjacent to the pool deck, you can walk out on the shared patio with multiple BBQ-Grills and covered outdoor dining tables. This outdoor space is perfect for a pool gathering & grill-out!brbrResort guests will have access to the heated pool, patio with sun-loungers, the dock on Heron Lagoon, kayaks, the courtyard for outdoor eating and grilling, ONE free-parking space (1 vehicle max), and beach gear that includes beach towels, chairs, cooler, blanket, cart and an umbrella. The laundry facilities are free and shared with other guests. The Hibiscus Bungalow`s veranda and the entire interior of your bungalow is exclusive to you!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches in Siesta Key. Unplug and explore your surroundings, such as Turtle Beach, one mile south from this location or Crescent Beach, just 2.5 miles north. Sporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. From cafes to fine dining in the area to the beautiful Siesta Key beaches, you will certainly find what you need.brbrDid we mention that we provide all guests a complementary beach gear that includes beach towels, chairs, blanket, cart, cooler and an umbrella.brbrYou will receive ONE free parking spot on-site (one vehicle max), thus if you’re looking to soak up the sun and tour the island in your own vehicle, you always have an easy place to park when you come back. If you don’t want to drive, take advantage of the free Siesta Key Breeze Trolley which stops right outside our parking lot every 20 minutes from 8AM - 10PM daily. Siesta Key Dreams is also happy to offer free baggage-drop off to make your travels easier.brbrIncluded with your reservation are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrella, blanket, cooler and a cart to transport your items easily!brbrTraveling with your children We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request! brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement and guest verification instructions, this allows us to provide a safe space and contactless check-in.brbrDo you have a large party Siesta Key Dreams offers 3-bungalow rentals or you rent the entire resort!brCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM - 7AM brPool Hours: 8AM - 9PMbrParking: 1 reserved parking space (one vehicle max)brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key DreamsbrPets: No PetsbrAdditional Details: See Vacation Rental Agreement for all details
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$730.05

/ Nightly
Private Vacation Home

Siesta Key Bungalows, the Lagoon Bungalows Complex

Siesta Key, Florida, United States

Steps away from a private entrance to Heron Lagoon, the Siesta Key Bungalow`s Lagoon Complex features three bungalows totaling 3 bedrooms, 3 kitchens, and 3 bathrooms. Guests will be in the Ringling, Catamaran, and Pineapple Bungalows. Each bungalow has a king bed, plus a queen sofa bed, allowing for 3 guests per bungalow. The three-bungalows are perfect for family and friend gatherings and can accommodate up to 9 guests total. brbrIn each unit, you’ll experience a bright and airy space with an open floor plan connecting a welcoming living room and kitchen with a stove, fridge, microwave, & Keurig. In a separate room, you’ll see your comfortable bed and a private bathroom fully stocked with linens, hair dryer, and toiletries for use. We are happy to provide free, high-speed internet & Wi-Fi, HD Television equipped with live sports & extensive channel options via DirecTV Satellite, and electric appliances so you will not miss a beat. Each bungalow either has a private deck or veranda; perfect for the Siesta Key experience, lagoon-side.brbrThis exclusive three bungalow complex leads out to a private deck surrounded by mangroves. The deck and chaise lounge chairs overlook the beauty of Heron Lagoon. Siesta Key Dreams provides complimentary kayaks during your stay, which can be launched off the dock area. The resort has a shared heated pool, patios, a courtyard, and grills, perfect for a relaxing day in the Florida sun. With this location being only a few miles away from Siesta Key’s top beaches, you will certainly find your getaway of choice.brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the beaches of Siesta Key. Unplug and explore your surroundings, such as Turtle Beach only one mile south of the resort. Or head to Crescent Beach which is just 2.5 miles north. Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. Sporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! From cafes to fine dining in the area and the beautiful Siesta Key beaches, you will certainly find what you need. brbrIf you’re looking to soak up the sun and tour the island, the free Siesta Key Breeze Trolley stops right outside the parking lot every 20 minutes from 8-12 PM daily. We are also happy to offer baggage drop-off to customize your stay. There is also on-site parking, and with this Bungalow Complex you will receive THREE parking spots!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement, and guest verification, this allows us to provide a safe space and contactless check-in.brbrDo you have a large party Siesta Key Dreams offers 3-bungalow rentals or you can even rent the entire resort! Contact us to learn more.brCheck Out: 10AMbrCheck In: 3pmbrQuiet Hours: 10pm - 7AM brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams (entire building rentals are available)brPets: Pet Friendly & Non-Pet Units are designated during the reservation process. Pets are not allowed unless explicitly listed on the unit listing. Pet Friendly units require deposit or waiver and additional cleaning/pet charge.brAdditional Details: See Vacation Rental Agreement for all details
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$801.12

/ Nightly
Private Vacation Home

Heron Lagoon, dock, pool, the Poolside Complex at Siesta Key Bungalows

Siesta Key, Florida, United States

Steps away from a heated pool on Heron Lagoon, the Poolside Bungalow Complex includes the Tortuga, Mermaid, and Sunset units. This listing provides 3 bedrooms, 3 kitchens, and 3 bathrooms. Each bungalow has a king bed, plus a roll-away single size bed or a queen sofa bed, allowing for 3 guests per bungalow. The three-bungalows are perfect for family or friend gatherings and can accommodate up to 9 guests total. brbrEach respective Bungalow has a bright and airy space with an open floor plan connecting a welcoming living room and kitchen with a stove, fridge, microwave, & Keurig. In each bedroom you’ll have a comfortable bed and a private bathroom fully stocked with linens, hair dryer, and care products. We provide free, high-speed internet, Wi-Fi, an HD Television equipped with live sports & extensive channel options via DirecTV Satellite. This set of three Bungalows surround the resort`s heated pool, and it also has a private lanai overlooking Heron Lagoon. Each bungalow has it`s own patio or veranda perfect for relaxing or entertaining.brbrThe Poolside Bungalow Complex is nestled on the west side of the resort, and is literal steps from both the lagoon and the heated pool. The resort has sun-loungers that overlook the beauty of Heron Lagoon. Launch a complementary kayak off the resort`s private dock and cruise around Heron Lagoon. Or take advantage of the shared heated pool, patios, courtyard, or grills. With this location being only a few miles away from Siesta Key’s top beaches, you will certainly find your getaway of choice.brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches of Siesta Key. Unplug and explore your surroundings, such as Turtle Beach one mile south of the resort or venture over to Crescent Beach just 2.5 miles north. Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. Sporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! From cafes to fine dining in the area and beautiful Siesta Key beaches, you will certainly find what you need. brbrIf you’re looking to soak up the sun and tour the island, the free Siesta Key Breeze Trolley stops right outside the parking lot every 20 minutes from 8-10PM daily. We are also happy to offer baggage drop off to customize your stay. Prefer to drive, we make that easy with on-site parking and THREE(only) reserved parking spots included with this reservation. brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement, and guest verification instructions, this allows us to provide a safe space and contactless check-in.brbrDo you have a larger party, we also rent the entire resort, contact us for more information!brCheck Out: 10AMbrCheck In: 3pmbrQuiet Hours: 10pm - 7AM brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams (entire building rentals are available)brPets: Pet Friendly & Non-Pet Units are designated during the reservation process. Pets are not allowed unless explicitly listed on the unit listing. Pet Friendly units require deposit or waiver and additional cleaning/pet charge.brAdditional Details: See Vacation Rental Agreement for all details
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Exceptional(5)

$893.33

/ Nightly
Private Vacation Home

Siesta Tropical Retreat - 5-Star Rated 3 Bedroom Pool Home in Siesta Key Village

Siesta Key, Florida, United States

Make Siesta Tropical Retreat your home away from home for a perfect stay in paradise.brbrFull renovation completed in early 2025 including a brand new kitchen, high end stainless steel appliances, all new furniture and high quality mattresses on all beds. Come and enjoy all of the new furnishings during your stay in paradise!brbrThis luxurious canal-front vacation home has everything you need for a fantastic stay on Siesta Key. Just steps to Siesta Key Village and a quick scenic walk to Siesta Key beaches. Enjoy the kayaks and bikes that are included with your stay. No car needed - walk, bike ride or take the free trolley all around Siesta Key. Please feel free to call or text the owner (Kathi, 908-255-8782) to inquire about discounted stays.brbrYour island life begins as you enter the completely renovated home with a clean, modern beach resort look and feel. You walk into the wide open spacious living area, with 2 living rooms, dining area and brand new kitchen where you can enjoy time with family or friends while also having plenty of room for everyone to have their own space. The kitchen has everything you need to prepare and enjoy meals at home if you choose and features quartz countertops and high end stainless steel appliances. Relax in either of the 2 living rooms, both include 2 couches and matching oversized chairs. One living room has a new a fold down leather Eurolounger that can provide comfortable additional bedding for up to 2 guests and can be used as a 4th bedroom (no door). 2 of the 3 bedrooms feature king size beds and beach inspired bedding and artwork. The 3rd bedroom features both a queen size bed and a twin xl bed to comfortably sleep 3. All bedrooms have flatscreen TVs, beach-white bedroom furniture, Ralph Lauren Polo blankets and built in closet organizers. The 2 full bathrooms are down the hall (one has a zero entry shower with rainfall showerhead). The entire house has been fully renovated. brbrWhen you enter Siesta Tropical Retreat, you look straight through the living area and through a long wall of sliding doors and become immediately drawn to the beautiful, very private, tropical backyard featuring an amazing private freeform pool/spa surrounded by palm trees, tropical plants and a large paver patio, luxurious lounge chairs, wireless speakers, stainless steel grill and outdoor dining table. The property is on a canal that features wildlife such as fish, ducks, herons and even manatee! There is nothing better than enjoying time in the pool and spa (enjoying music, drinks and possibly a manatee sighting) after a long day at the #1 beach.brbrNo need to worry about packing miscellaneous items for your vacation. Siesta Tropical Retreat is furnished with everything you need including pool and beach toys, shovels/pails, fishing rods/bait buckets, bikes, kayaks, beach chairs, beach carts, coolers, all high quality linens/pillows, bath towels, fluffy beach towels, outdoor towel drying rack, washer/dryer, outdoor grill, plus a fully furnished kitchen. Enjoy dinner at home by the pool, or check out all of the wonderful dining options in Siesta Key Village just a minute or two walk down the street. brbrSiesta Tropical Retreat includes everything needed for a wonderful vacation, just book your stay, pack your bathing suits, and get ready to enjoy your relaxing vacation at this island oasis! brbrPlease note: Per zoning laws, we are allowed one rental guest per month. Since we try to stay there in between shorter term guests, please inquire about your desired dates and we are often able to accommodate. Minimum booking 2 weeks (Dec 15 - Jan 1) and 30 days (Jan - Mar). Pool heat fee (if heat option chosen) $100/week. Pet fee $250/stay. br brFeel free to contact the owner, Kathi, directly to discuss available discounts via text at 908-255-8782.
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$626.03

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Private Vacation Home

Heated Pool, Dock, Kayaks, on Lagoon, Turtle Beach 1-mile & Crescent Beach 2-miles, 3-units

Siesta Key, Florida, United States

Steps away from a private-dock on Heron Lagoon, this 3-Bungalow Complex includes the Coquina, Dolphin, and Coconut units. This listing provides 3 bedrooms, 3 kitchens, and 3 bathrooms. Each bungalow has a king bed, plus a sofa that turns into a queen mattress, allowing for 3 guests per bungalow. The three-bungalows are perfect for family or friend gatherings and can accommodate up to 9 guests total. brbrEach respective Bungalow has a bright and airy space with an open floor plan connecting a welcoming living room and kitchen with a stove, fridge, microwave, & Keurig. In each bedroom you’ll have a comfortable bed and a private bathroom fully stocked with linens, hair dryer, and care products. We provide free, high-speed internet, Wi-Fi, HD Television equipped with live sports & extensive channel options via DirecTV Satellite. Each bungalow has it`s own backyard patio and veranda perfect for relaxing or entertaining.brbrThis exclusive Three-Bungalow Complex is nestled on the east side of the resort. The resort has sun-loungers that overlook the beauty of Heron Lagoon. Launch a complementary kayak off the resort`s private dock and cruise around Heron Lagoon. Or take advantage of the shared heated pool, patios, courtyard, or grills. With this location being only a few miles away from Siesta Key’s top beaches, you will certainly find your getaway of choice.brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches of Siesta Key. Unplug and explore your surroundings, such as Turtle Beach one mile south of the resort. Or venture over to Crescent Beach just 2 miles north. Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. Sporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! From cafes to fine dining in the area and beautiful Siesta Key beaches, you will certainly find what you need. brbrIf you’re looking to soak up the sun and tour the island, the free Siesta Key Breeze Trolley stops right outside the parking lot every 20 minutes from 8AM - 10PM daily. Siesta Key Dreams is also happy to offer baggage drop off to customize your stay. There is also three (only) on-site parking spaces.brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrAfter you book your reservation, you will receive a message that has more details about your stay, and a link to the `boarding-pass` which includes the house rules agreement, guest verification, and security deposit instructions, this allows us to provide a safe space and contactless check-in.brbrDo you have a larger party, we also rent the entire resort, contact us for more information!brbrBeaches:brTurtle Beach: ~1.0 mile southbrCrescent Beach: ~1.4 to 2.1 miles northbrSiesta Key Beach: ~3.1 to 3.4 miles northbrbrLocal Landmarks & Entertainment:brSanderling Beach Club: ~0.9 milesbrPoint of Rocks: ~1.1 milesbrSiesta Key Village: ~4.3 miles north (the island`s main hub for dining and shopping)brHistoric Spanish Point: ~10-minute drivebrMarie Selby Botanical Gardens: ~7.4 milesbrCheck Out: 10AMbrCheck In: 3PMbrQuiet Hours: 10PM - 7AM brPool Hours: 8AM - 9PMbrParking: Three vehicle maxbrNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams (entire building rentals are available)brPets: No petsbrAdditional Details: See Vacation Rental Agreement for all details
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Exceptional(1)

$3229.57

/ Nightly
Private Vacation Home

Entire Resort on Heron Lagoon, the Siesta Key Bungalows

Siesta Key, Florida, United States

The Siesta Key Bungalows is an exclusive resort within the Siesta Key Dream’s portfolio of vacation rentals & features 10 unique Bungalows. Each Bungalow has a living room, bedroom with a king or queen bed, roll-away single bed, full kitchen, & full bathroom. Nestled on the banks of Heron Lagoon in Siesta Key, FL, guests have access to the private heated pool, exclusive dock, kayaks, grills, patios, courtyard & parking lot. Perfect for large groups, the resort can accommodate up to 30 guests.brbrEach Bungalow has a bright and airy suite with an open floor plan connecting a welcoming living room and kitchen with a stove, fridge, freezer, microwave, & Keurig. In the bedrooms, you’ll have a comfortable bed and a private bathroom fully stocked with linens, hair dryer, and care products. We are happy to provide complimentary high-speed internet, Wi-Fi, HD Television equipped with live sports & extensive channel options via DirecTV Satellite and electric appliances so you will not miss a beat. With either a private patio, veranda, deck or lanai each Bungalow has a unique space to enjoy the Siesta Key weather.brbrThis exclusive resort is surrounded by mangroves exporting our guests from the everyday hustle. The deck and chaise lounge chairs overlook the beauty of Heron Lagoon. For those who want to get even closer to the natural surroundings of Siesta Key, kayaks can be launched from the resort`s exclusive dock. brbrThe resort`s heated pool and outdoor spaces are a perfect place to bask in the Florida sun! The pool is surrounded by an array of palm trees, mangroves and tropical plants, providing a beautiful backsplash of greenery and partial shade. On the pool deck, you’ll find numerous lounge chairs, views of Heron Lagoon and a tranquil atmosphere. Adjacent to the pool deck, you can walk out to the patio and enjoy a grill-out with seating at covered tables.brbrSiesta Key Dreams always shows our exact location in our listings, so our guests know exactly how close they truly are to Heron Lagoon and the nearby beaches of Siesta Key. Unplug and explore your surroundings, such as Turtle Beach one mile south from this location or Crescent Beach, just 2.5 miles north. Crescent Beach has the famous Point of Rocks, a hotspot for snorkeling and diving to view the tropical wildlife of Siesta Key. Sporty and less crowded, Turtle Beach offers picnic areas, a playground, volleyball court, and a plethora of sea shells to hunt for! From cafes to fine dining in the area and beautiful Siesta Key beaches, you will certainly find what you need. Did we mention that we provide all guests a complementary ‘beach-loud-out’ that includes beach towels, chairs, blanket, cart, cooler and an umbrella.brbrIf you’re looking to soak up the sun and tour the island, the free Siesta Key Breeze Trolley stops right outside the parking lot every 20 minutes from 8-10 PM daily. Siesta Key Dreams is also happy to offer baggage drop off to customize your stay. There is also on-site parking, and you will receive 10 parking spaces!brbrOur Guest Operations team has a combined 20+ years of customer service, operations, and management experience. Our guests are supported both locally in Siesta Key by a Guest Experience Manager, and virtually by your host. In addition to passionate operations professionals, the ownership group is engaged; highly involved in the decor, property improvement, and guest experience. It is not uncommon for our guests to unknowingly bump into or speak with the owners during their vacation :)brbrAfter you book your reservation, you will receive a message that has more details about your reservation, and a link to the `boarding-pass` which includes the house rules agreement, and guest verification instructions, this allows us to provide a safe space and contactless check-in.brbrPlease contact us if you wish to discuss payment options!brCheck Out: 10AMbrCheck In: 3pmbrQuiet Hours: 10pm - 7AM brNo smokingbrLarge Gatherings (1.5x Guest Occupancy): Require approval from Siesta Key Dreams (entire building rentals are available)brPets: Pet Friendly & Non-Pet Units are designated during the reservation process. Pets are not allowed unless explicitly listed on the unit listing. Pet Friendly units require deposit or waiver and additional cleaning/pet charge.brAdditional Details: See Vacation Rental Agreement for all details
Bed 10

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Bath 10

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Sleep 30

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Exceptional(2)

$430.07

/ Nightly
Private Vacation Home

Tropical Siesta Key Villa w/ Private Patio & Pool Access in Polynesian Gardens

Siesta Key, Florida, United States

Serene Siesta Key Villa in Polynesian GardensbrbrEscape to this charming 3-bedroom, 2-bathroom villa nestled in the lush and tranquil Polynesian Gardens neighborhood on Siesta Key. Perfectly designed for relaxation and comfort, this tropical retreat offers the best of coastal living, with thoughtfully curated spaces both indoors and outdoors.brbrInside the Villa:brbr Spacious Living Room: Unwind in the airy and inviting living area featuring plush leather seating, a cozy reading nook, and sliding glass doors leading to a screened-in lanai. The custom entertainment center adds warmth and elegance to the space.br Gourmet Kitchen: Cook up your favorite meals in the modern, fully stocked kitchen with stainless steel appliances, an oversized island, and charming pendant lighting. A walk-in pantry provides ample storage space for all your essentials.br Dining Area: Enjoy family meals in the beautifully appointed dining room with large windows and soft natural lighting that enhances the serene ambiance.br Bedrooms:br Master Bedroom: Luxurious king bed, private ensuite bathroom, and direct access to the backyard patio.br Second Bedroom: Queen bed with charming décor and natural light.br Third Bedroom: Two twin beds with vibrant, cheerful bedding perfect for kids or additional guests.brbrOutdoor Spaces:brbr Private Backyard Patio: This tropical oasis features lush landscaping, cozy seating, and ample privacy for enjoying quiet mornings or starry evenings.br Screened-In Lanai: Overlooking the tree-lined street, this space is ideal for sipping morning coffee or winding down after a day of exploring Siesta Key.brbrCommunity Amenities:brbr Large Heated Pool: Take a refreshing dip in the community pool surrounded by tropical greenery.br Intercoastal Dock: Watch the boats pass by or cast a line from the dock for a peaceful escape.br Charming Neighborhood: Stroll through the quiet, tree-lined streets of this old Siesta Key neighborhood, filled with charm and character.brbrPerfectly Located:brbrJust a ½ mile walk to Beach Access #10, you'll enjoy the powdery white sands and turquoise waters of Siesta Key Beach. Explore nearby restaurants, boutique shops, and vibrant nightlife in Siesta Key Village, all within minutes of your doorstep.brbrWhether you're seeking a relaxing retreat or a fun-filled family vacation, this villa offers the perfect balance of comfort, style, and location. Book your stay today and create unforgettable memories in the heart of Siesta Key! brbr brWhat's provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner.
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Bath 2

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