Vacation Rentals By Owner In Siesta Key, FL

Bali Hai House | Canal-Front Home with Private Heated Pool, Near Siesta Key Villagebrbr Why You'll Love This HomebrBali Hai House places you on a quiet canal in Siesta Key, offering private waterfront views while remaining close to the island's most popular spots. Located less than 1 mile to Siesta Key Village and under 1.5 miles to Siesta Key Public Beach Access 2, this three-bedroom retreat balances convenience with a peaceful residential setting. With a screened-in patio, private heated pool, and direct canal access, the outdoor spaces are designed for spending time together while staying connected to the water.brbr ‍ ‍ Perfect ForbrFamilies and small groups seeking a waterfront Siesta Key stay with private pool access and proximity to both the beach and village dining.brbr ️ Imagine ThisbrStart the morning on the screened patio overlooking the canal as wildlife moves quietly across the water. Brew coffee in the kitchen and plan the day, whether that means heading to Siesta Key Beach for a morning swim or strolling through Siesta Key Village for breakfast and shopping. In the afternoon, return home to cool off in the private pool or stretch out in the hammock while others gather around the outdoor seating area. Cast a fishing line directly from the canal's edge or simply settle into a quiet moment by the water. As evening approaches, light the fire table and share laughs outdoors, or unwind inside in the comfortable living area before retreating to your private bedroom space.brbr Where You'll Sleepbr• Bedroom 1: King Bed – Sleeps 2br• Bedroom 2: King Bed – Sleeps 2br• Bedroom 3: King Bed – Sleeps 2br• Living Room: Queen Sleeper Sofa – Sleeps 2brbrAccommodates up to 8 guests.brbr Explore The Areabr• 0.8 Miles to Siesta Key Village - Dining, Boutiques, Coffee Shops, and Live Musicbr• 1.5 Miles to Siesta Key Beach - Wide Sand, Gulf Swimming, and Beach Accessbr• 3.6 Miles to Point of Rocks - Perfect for Snorkeling and Shellingbr• 5.0 Miles to Downtown Sarasota - Options for Restaurants, Shows, and Nightlife. brbr⌛ Don't WaitbrYour reservation includes peace of mind through our CottageClean™ program, featuring a six-hour deep clean followed by a detailed 35-point inspection prior to arrival.brbr Need to KnowbrPer Sarasota ordinance, this property is limited to one rental per 30-day period. Reservations must comply with Sarasota County regulations. The pool is heated from November 15th to April 15th. During cooler weather, heating performance may vary depending on outdoor temperatures.

Bali Hai House | Canal-Front Home with Private Heated Pool, Near Siesta Key Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$796.61

This private vacation home blends comfort, style, and location. With 3 king-sized bedrooms, a private heated pool, and tropical landscaping, Barefoot Bungalow is among the finest Siesta Key rentals with pool for families or couples. Located just steps from the beach and close to the best restaurants, shops, and nightlife, this spacious, fully furnished villa sleeps up to 6 guests and offers everything you need for a peaceful island stay.

Private home with Heated pool 1 Block to beach

Siesta Key, Florida, United States

3

Bed

3

Bath

Sleeps

$306.54

Enjoy this Key West style cottage equipped to sleep 3 guests. Boasting 2 bedrooms and 1 bath, the master bedroom has a king bed and the second room has a twin. Great for small families travelling and looking to save on some meal cooked in with the kitchenette which can handle most home cooked meals. Also relax on your private screened in porch after a day tanning in the sun as the beach is 100 ft away! With roughly 400 sqft of living space you will surely be able to relax and immerse yourself in the beach life of Siesta Key!

Cottage

Blue Dolphin Cottage steps from the beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$450.97

Your Perfect Family Beach Haven on Siesta Key:brDiscover the ultimate family getaway in this beautifully modernized beach house, thoughtfully designed to make your vacation effortless and memorable. Just one mile from world-famous Siesta Key Beach, this stunning home offers the perfect balance of relaxation and adventure for families seeking their dream beach escape.brbrIndoor Comfort Meets Outdoor Paradise:brbrStep into your private oasis featuring a heated, screened pool surrounded by a spectacular lanai – perfect for family dinners under the stars or lazy afternoons on comfortable chaise lounges. Fire up the BBQ while the kids splash in the pool, or gather at the bistro set for morning coffee and vacation planning.brbrComfortable, Modern Living:brbrInside, the home flows seamlessly between welcoming spaces designed for family time and relaxation. The contemporary living room features a 60 smart TV, while a separate cozy family room offers the perfect spot for board games or quiet reading. The heart of the home is the fully equipped, modern kitchen, complete with new appliances, a generous island, and comfortable counter seating – ideal for family meals and snack time.brbrAnd rest easy... every bedroom is a private retreat, featuring:brbrIndividual smart TVs for winding down in the evening brBlackout blinds for perfect vacation sleep-insbrUSB charging ports in wall outlets for everyone's devicesbrbrBeach ready with everything you need: brbr6 adult beach cruiser bikes for family adventuresbrComplete beach setup with chairs, cart, umbrella, and beach gamesbrBeach towels and an outdoor shower to rinse off the sand when you return home brbrPrime Location:brbr1-mile ride to Siesta Key Public Beach, where you will find the famous colorful life guard stations!br2-mile ride to Siesta Key Village's restaurants and shopsbrEasy access to local entertainment and live musicbrConvenient Frog Hop trolley service available to get around the island brbrWhether you're planning active beach days or poolside relaxation, this thoughtfully appointed home offers everything your family needs for the perfect Siesta Key vacation. Create lasting memories in this ideal blend of comfort, convenience, and coastal charm. Minimum 28-day rental to comply with local laws for residential area.

Beautiful beach house with heated pool, 1 mile to Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$459.7

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Siesta Dunes Modern Coastal Retreat! brbr brbrEscape to Siesta Dunes, a gated resort offering a private beach on Siesta Key’s stunning Gulf Coast. Enjoy direct beach access, a saltwater pool, a hot tub, and tennis courts, all just steps away from this beautifully updated first floor, end unit condo. With a spacious layout, modern amenities, and a private outdoor space, this vacation home offers the perfect blend of relaxation and adventure. brbr brbrLOCATION HIGHLIGHTS: brbr- Gated community with private beach access brbr- Heater community pool and hot tub, tennis/pickleball courts brbr- Sun decks, loungers, and BBQ grills just minutes from the unit brbr- 6 minute drive to Siesta Key Village brbr- Assigned parking spot brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom ground floor unit brbr- Close to complex entrance gate, easy access to Midnight Pass Road brbr- Short couple minutes walk to the beach access and pool brbr- Keyless entry brbr- Dedicated WIFI and cable brbr- Private washer and dryer brbr brbrLIVING ROOM: brbr- Coastal furnishing with access to screened lanai outlooking the back area brbr- Smart TV with cable brbr- Floor to ceiling sliders to let in natural light brbr brbrKITCHEN AND DINING: brbr- Fully equipped modern kitchen with quartz countertops brbr- Stainless steel appliances and all cooking essentials brbr- Dining area with seating for 4, plus 2 more at the breakfast bar brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Suite: Double queen bed, flat-screen TV, walk-in closet, en-suite bath, direct access to open-air deck brbr- Guest Bedroom: Two twin beds, flat-screen TV, walk-in closet brbr- Master ensuite bathroom: large rain shower and separate water closet brbr- Guest bathroom: tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrNEARBY FAVORITES: brbr- Clayton’s Grill, Miguel’s, Captain Curt’s, Anna’s Deli, Orange Octopus, Crescent Beach Grocery, and more within walking distance brbr- Boat & water sport rentals nearby brbr- Post office close by for sending postcards home brbr brbrIMPORTANT INFO: brbr- No pets allowed brbr- No smoking or vaping brbr- Weekly minimum stay off season, 2 week min during high season brbr- Guests must follow resort rules (including parking limits) brbr- Rental registration and parking passes required brbr- No boats, trailers, jet skis, golf carts, motorcycles, or oversized/commercial vehicles. No golf carts allowed brbr- Roofing project is scheduled to start the first week of May 2026 (completion in about a month, weather permitting) brbr brbrWHETHER YOU'RE ENJOYING THE SUNSET ON THE BEACH, GRILLING UP A MEAL, OR RELAXING IN THE COMFORT OF YOUR CONDO, THIS PROPERTY OFFERS THE PERFECT ESCAPE FOR YOUR NEXT BEACH VACATON!brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Siesta Dunes Modern Condo | Private Beach | Heated Pool | Ideal Location | Beach Gear Provided!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$839.43

Nestled in Siesta Key on Palm Island, this delightful house offers 3 bedrooms: 1 king bed, 1 queen bed, and 2 bunk beds. With 2 bathrooms featuring a bathtub and shower, guests can relax and unwind after a day of exploring. Heating and AC ensure a comfortable stay year-round. Enjoy your time in Siesta Key at our lovely house.

Beautiful 3 bedroom home with heated pool! Half a mile to Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$227.34

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.br* Anchorage Resort Condo br* 2 bedrooms / 2 bathroomsbr* Sixth Floor Condo with balcony overlooks Southern Siesta Keybr* Fully equipped Kitchen with seating for 4 at the dining table and 4 at kitchen islandbr* Beach Supplies include- Chairs, Umbrella, Cooler, Raft/Float Items, Beach Towelsbr* Community Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* Elevatorbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Sixth Floor Condo)brBedroom 1: One King Bed (Ensuite Bathroom) / Balcony Access / 55 Smart TVbrBedroom 2: Two Queen Beds / Balcony Access / 50 Smart TVbrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size Poolbr* 3 Lighted Tennis/Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike & Kayak Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each FloorbrbrPool Information:br- Community Poolbr- Heated brbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybr brbrDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 2 Bedroom Condo 6th Flr, Beach Access, Pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$217.64

Summary:brbrQuaint 1 bedroom bungalow with Murphy bed that folds into the wall during the day providing additional living space. Living room w/leather furniture, French doors open to a private brick patio. 2 Smart TVs (43-inch in living room and 32-nch in bedroom). Kitchen offers a mini convection oven w/ burners above oven, microwave and toaster. Additional hot plate burners in cupboard for total of 4 burners. High speed internet. Located in Village 1 block from restaurants and shops. Small dog allowed$300brbrbrbrOther Things to Note:brbrMust be 25 years old or older to book.

Apartment

5239 Avenida Navarra in Village

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$426.1

Upon entering this unit, you experience the fantastic view of shining gulf waters and the powder white crystal sand beach. Master bedrooms offers king bed and beautifully remodeled bathroom and boasts more of the stunning beach views, including direct access to the balcony! brbrYou can enjoy waking up to a fresh cup of coffee as you listen to waves roll in from offshore or unwind at the end of each day sipping your favorite glass of wine as you watch the sunsets over the Gulf of Mexico. brbrOur Accommodations are just 2 miles from the popular Siesta Key Village with shops, restaurants, bars, coffee shops and more or a short walk to nearby restaurants, convenience stores, and water sports rentals! Siesta Key also provides free trolley service that stops right in front of the resort.brbrCrystal Sands' resort-like amenities include private access to Siesta Key's famous powdery, white-sand beaches and 2 heated swimming pools. If you are looking for a family vacation or a romantic getaway Crystal Sands is the perfect place for you. Come stay with us at the most exclusive resort on Siesta Key that offers the best beachfront views on the island!br

Crystal Sands Tower Unit 1002 - Beachfront

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$225.37

Just knowing you have a scenic trip to Siesta Key on the calendar is exciting. Knowing you've booked your stay in Beach Road-Capri only makes it that much better! This vacation home away from home is a charming beachside property featuring 1-bath studio within a floorplan that's fantastic for welcoming up to 4 guests during a stay. Whether you're headed to Siesta Key for a solo adventure, can't wait to spend time with your significant other or have a small group trip planned, Beach Road-Capri offers up the space, style, and proximity to fun that everyone deserves to enjoy.brbrSettle into the Best of Siesta Key LocationsbrbrBooking a stay in Beach Road-Capri is a great way to ensure that your trip includes seamless access to fun. This property is situated just across the street from iconic Siesta Key Beach, making it easier than ever to grab an umbrella and a chair and make the most of a day under the sun. Those looking to enjoy time shopping, dining, bar hopping, or savoring nightlife venues will love that Beach Road-Capri is no more than a half-mile north of Siesta Key Village. Just around the corner from this home, the free Siesta Key Trolley stop can be found, providing guests with access to all of the Siesta Key landmarks with ease. brbrInterior Amenities to EnjoybrbrBeach Road-Capri enjoys a cozy and comprehensive floor plan that's open-concept in nature and allows for plenty of natural light to flow through spacious windows. Throughout this property, guests will enjoy a balance of home-inspired comforts and beach-inspired design elements that make for an elegant and welcoming stay. The main living room hosts a sofa topped with colorful throw pillows in front of a coffee table. Across from the sofa a flat-screen television is mounted on the wall and just below, guests can sit and dine on the bar style countertop for two when it's time to enjoy a meal together. The kitchen in Beach Road-Capri includes an efficient lineup of appliances including an 3-1 microwave, oven, and air fryer, oven, sink, refrigerator, stove, and Keurig coffee maker too. brbrWhen it's time to rest after a day of Siesta Key fun, the bedroom in this property showcases an inviting king bed topped with high-quality linens and an elegant comforter. When added sleeping space is needed, a queen Murphy bed is available as well. brbrBook Your Stay TodaybrbrMake the most of every moment in Siesta Key when you partner with the property professionals at Rent Siesta Key. Reach out today to learn more about booking a stay in Beach Road-Capri the next time your travel plans bring you this direction.brbrPARKING: There is only room for 1 vehicle for this unit.

Apartment

Studio Retreat Across the Street from Beautiful Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$246.51

Never miss a beach-scape sunset when you are just a couple hundred meters from Americans #1 beach, Siesta Key Beach. Enjoy this two bedroom two bathroom condo style unit in a great location: a short walk to the beach on a quiet street but just minutes from shops, bars, and restaurants. The unit offers a full kitchen large enough for TWO cooks in the kitchen..., breakfast bar, an open dining area and living room. The living room is furnished with a flat screen TV. Open the large sliding glass doors out to the spacious screened patio with lounge seating and table. The master bedroom with ensuite bathroom is furnished with a king-size bed and TV. The guest bedroom is furnished with a Queen-size bed and TV. The backyard of the property offers a heated pool, plenty of sun bathing spots, and a BBQ area. There are two twin-size rollaway beds available for guests. Free high speed WiFi is available throughout the property including the pool area.brbrMinimum Reservation Requirement: 1 week minimum Saturday to Saturday during peak season.

Fully Renovated Beachside Getaway with Heated Pool – Walk to Restaurants

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$266.03

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brAnchorage Resort Condo - Corner Unitbr2 bedrooms / 2 bathroomsbrSpacious Balcony overlooking Southern and Western Siesta KeybrThird Floor Condo overlooks the canal and Gulf of MexicobrFully equipped Kitchen with seating for 4 at the dining tablebrBeach Supplies include- Chairs, Umbrella, Raft/Float Items, Beach TowelsbrCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the streetbr25-year minimum age to rent restrictionbrbrBEDROOMS (Third Floor Condo)brBedroom 1: One King Bed (Attached Bathroom) / Balcony AccessbrBedroom 2: Two Double Beds (Attached Bathroom) / Balcony AccessbrbrPool Information:br- Community Poolbr- Heated brbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike & Kayak Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each Floorbr brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 3rd Floor 2 Bedroom Condo South/West Balconies

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$372.03

Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brAnchorage Resort Condo on Siesta Key br2 Bedrooms / 2 BathroomsbrEighth Floor Condo with Balcony overlooking North-Western Siesta KeybrFully equipped Kitchen with Seating for 4 at the Dining TablebrBeach Supplies include - 4 Beach Chairs, Beach Towels, Beach Umbrella, Cooler & Beach CartbrCommunity Pool- Largest pool on the Key!brGated Community and Parking includedbrSiesta Key Trolley- Free pickup in front of the Resort entrancebrPrivate Beach access to Crescent Beach across the street!brbrbrGuests staying at The Anchorage on Siesta Key have access to America’s #1 beach.brbrEasily accessible by one of two bridges connecting to the mainland of Sarasota, Siesta Key is an 8-mile long, crescent-shaped barrier island with four main areas – Siesta Beach, Crescent Beach, Turtle Beach, and Siesta Key Village.brbrbrREFUNDABLE DAMAGE DEPOSIT: $300 will be added to total as a refundable damage deposit. This amount will be refunded after the check out, if no damage to the property has been detected during your stay.brCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the street

Lovely 2bd condo close to the beach (AN1145)

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$351.43

Our 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brAnchorage Resort Condo br2 bedrooms / 2 bathroomsbrNinth Floor Condo with balcony overlooks North-Western Siesta Key- Gulf Views!brFully equipped Kitchen with seating for 4 at the dining tablebrBeach Supplies include- 4 Chairs, Umbrella, Beach CartbrCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the streetbrbrbrGuests staying at The Anchorage on Siesta Key have access to America’s #1 beach.brbrEasily accessible by one of two bridges connecting to the mainland of Sarasota, Siesta Key is an 8-mile long, crescent-shaped barrier island with four main areas – Siesta Beach, Crescent Beach, Turtle Beach, and Siesta Key Village.brbrbrREFUNDABLE DAMAGE DEPOSIT: $300 will be added to total as a refundable damage deposit. This amount will be refunded after the check out, if no damage to the property has been detected during your stay.brCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the street

Gorgeous 2bd condo near the beach (AN1079)

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$484.39

When a beach getaway infused with luxury and style sounds like a refreshing change of pace, you'll find everything you need when you book Miramar for your next trip this way. Miramar is a welcoming 4-bedroom, 3.5-bath home away from home that can accommodate up to 11 guests at a time. Whether your plans bring you here with a group of friends in tow or you're excited to spend quality time with the entire family, booking a stay in Miramar keeps you close to area fun while making the most of comfort, luxury, and style along the way. This multi-level property provides seamless access to Siesta Key Beach and comes with the decorative details and modern amenities throughout the make a great stay absolutely unforgettable.brbrInterior AmenitiesbrbrHigh-end furnishings, space, and ample light are yours for the enjoying when you book a stay in Miramar. Every level of this stunning home enjoys open concept design elements paired with large windows and vaulted ceilings. The result is a home that offers up an enhanced sense of living space as well as maximum Florida light flow and a fantastic frame on the view at all times. Guests who stay here can move easily between levels using the home's built-in elevate that runs from the garage all the way to the upper-level master suite. brbrThe living room in Miramar is a wonderful place to kick back in style. Here, guest will find a plush sofa and two decorative armchairs settled in front of a large flat-screen television and brick-framed fireplace too. A wall of windows allows guests to savor the sight of surrounding tropical foliage while the modern area rug is a beautiful offset to the rustic chic wood ceiling panels overhead. brbrThis room opens up to the dining area and kitchen where a home-cooked meal can always be created on a whim. The kitchen features an inviting wrap around breakfast bar with seating options paired with modern appliances and custom cabinetry already stocked with cookware and utensils. When it's time to dine together, guests can gather around the large formal dining table fit for 8-guests. brbrGetting a good night's sleep in Miramar is simple. Guests will love that every bedroom offers up a space of peace and tranquility to enjoy. The master bedroom hosts a king bed and en suite bath complete with a walk-in shower. Two additional bedroom host queen beds while the fourth enjoys two twin beds which is ideal for those traveling with little ones in tow. brbrWhen sleep eludes you and you're looking for added fun during your stay instead, make sure to make time to check out the screen room and wet bar located on the 4th floor!brbrExterior FeaturesbrbrWhile a stay in Miramar puts you in a prime location for exploring your surroundings, this home also has plenty of outdoor fun to offer right on-site. Guests can enjoy access to the property's private pool during their stay as well as the outdoor kitchenette when an alfresco meal is a priority. The home is equipped with no less than three outdoor patios that offer up a space to savor the sights and indulge in the fresh air at a moment's notice.brbrBook Your Getaway TodaybrbrEnjoy every moment of your Siesta Key adventure and make sure you have the luxurious accommodations to match! Have questions Send us a message — we'd love to help you plan your stay!brbrMINIMUM STAY REQUIREMENTS: One week minimum reservation required. Saturday to Saturday in most cases.brbrOptional:brbrPool Heating: $25/night for less than 3 weeks or $15/night for 3 or more weeks.

Luxury Home w/ Heated Pool and Private Beach Access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$316.54

Our House at the Beach E-302 by Tropical Sands Accommodationsbr1055 Beach Road, Sarasota, FL 34242brbrWelcome to Our House at the Beach E-302, a recently refreshed two-bedroom, two-bath condo located directly across from world-famous Siesta Beach. This bright coastal retreat sits within the coveted Our House at the Beach community, offering stunning beach views, easy walkability to Siesta Key’s sugar-white shoreline, and quick access to Siesta Village for dining, shopping, and island activities. Fresh interiors, comfortable furnishings, and desirable shared amenities make this a perfect choice for couples, small families, or guests seeking a relaxing Siesta Key escape.brbrHighlightsbr• Less than a 5-minute walk to Siesta Beachbr• 2 Bedrooms / 2 Bathroomsbr• 1 King bed, 2 Full bedsbr• Beach viewsbr• Shared heated community poolbr• Shared pickleball and tennis courtsbr• Beach chairs providedbr• Washer and dryerbr• 1 covered carport parking spacebr• Newly refreshed interiorbrbrGuests will enjoy access to the heated community pool, perfect for morning laps or an afternoon cool-down after a beach day. The community also features shared pickleball and tennis courts, ideal for friendly matches during your stay, as well as a grilling area for relaxed outdoor meals. With beach views and quick access to the shoreline, this condo offers the best of coastal living in a highly desirable Siesta Key location.brbrStep into a bright and newly refreshed living area designed for comfort and easy relaxation. The open-concept layout features cozy seating, a flat-screen TV, and large windows that bring in natural light and beach views. The fully equipped kitchen offers everything needed for home-cooked meals, including a refrigerator, stove, oven, dishwasher, microwave, toaster, regular drip coffeemaker, and Keurig. Enjoy meals at the dining table or take your morning coffee to the balcony overlooking the water.brbrThe primary bedroom offers a peaceful retreat with a king bed, ample storage, and an ensuite bathroom for added privacy. The second bedroom features two full beds, making it ideal for families or groups. The additional bathroom is conveniently located and equipped with a shower and bath combination, providing comfort for all guests.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroombr• Second Bedroom: Two full beds, access to hallway bathroombrbrThis condo includes a washer and dryer, beach chairs, and one covered carport parking space. Its central Siesta Key location places guests minutes from Siesta Village, Beach Road dining spots, island boutiques, and beautiful Gulf-front walking paths.brbrWith its newly refreshed interior, beach views, and unbeatable proximity to Siesta Beach, Our House at the Beach E-302 offers the perfect blend of comfort, convenience, and classic Siesta Key charm. Reserve your stay with Tropical Sands Accommodations today and enjoy a relaxing coastal retreat steps from one of the nation’s top-ranked beaches.

Our House at the Beach E-302 by Tropical Sands Accommodations

Siesta Key, Florida, United States

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$477.27

Sundown Sanctuary by Siesta Key Luxury Rental Properties brbrWelcome to Sundown Sanctuary, a refined four bedroom, three and a half bath Siesta Key luxury rental that blends iconic mid-century modern design with effortless coastal living. Set along Midnight Pass Road in a tranquil North Siesta Key neighborhood, this architecturally significant estate offers a private 30-foot lap pool with waterfall, a serene Zen garden, and a detached two bedroom guesthouse. Tucked beside a protected nature preserve and just an 18-minute walk to the Beach, the home is also minutes from Siesta Village, making it ideal for families, couples, and design-forward guests seeking privacy, space, and island-inspired comfort. Four on-site parking spaces are available. brbrHighlights br• 18-minute walk to the Beach br• 4 Bedrooms / 3.5 Bathrooms br• 1 King, 4 Queens, 1 Queen Murphy bed br• Private 30-foot lap pool with waterfall br• Separate two-bedroom guesthouse with full kitchen br• Private Zen garden with pond and sculpture br• Adjacent to a Sarasota County nature preserve br• Screened porch and multiple outdoor lounge areas br• Beach chairs and beach cart provided br• Washer and dryer br• Pet-friendly with approval br• 4 Parking spaces brbrDesigned for luxury coastal living, Sundown Sanctuary’s outdoor spaces set the tone for a restorative stay. The private lap pool, accented by a cascading waterfall, anchors the gated courtyard and invites morning swims or sunset relaxation. Surrounding lounge seating, a shaded hammock area, and sculptural elements create a peaceful tropical retreat. The Zen garden offers a quiet escape among palms and stone pathways, while the screened porch and outdoor seating areas provide comfortable spaces to gather throughout the day. brbrInside, the home celebrates its mid century heritage with airy, open concept living spaces, floor to ceiling windows, and curated art pieces that feel both elevated and inviting. The main living area features modern furnishings and a sleek fireplace, creating a comfortable setting for relaxing evenings. The main floor bar kitchen includes a small fridge, counterspace, and stovetop for quick meals and snacks. A spacious dining area flows seamlessly into the living room, making the layout ideal for entertaining or unwinding after a day at the beach. The second level of the main house includes the full kitchen, outfitted with granite countertops, stainless steel appliances, and ample workspace for preparing everything from quick breakfasts to shared family dinners. brbrThe main house features two thoughtfully styled bedrooms on the second level, with calming tones and Scandinavian inspired details. The primary bedroom offers a king bed and shares a full bathroom with a shower and tub combination. The second bedroom includes a queen bed and shares the same bath. A bonus room with a queen Murphy bed provides additional flexibility for guests. On the ground floor of the main house, a full bathroom with walk-in shower adds convenience. br brThe detached guesthouse is perfect for extended families or guests seeking added privacy. It includes two queen bedrooms connected by a Jack-and-Jill bathroom with walk-in shower, along with a full kitchen, cozy living area with fireplace, and a screened porch overlooking the courtyard. brbrRoom Details brMain House br• Primary Bedroom (Second Floor): King bed, shared bath with shower and tub br• Second Bedroom (Second Floor): Queen bed, shared bath br• Bonus Room: Queen Murphy bed br• Ground Floor: Full bathroom with walk-in shower brbrGuesthouse br• Bedroom 1: Queen bed br• Bedroom 2: Queen bed, Jack-and-Jill bath with walk-in shower brbrGuests will enjoy thoughtful conveniences including an outdoor shower, BBQ grill, private parking, beach chairs, and a beach cart. The home’s location near a nature preserve enhances the sense of serenity while still offering easy access to the beach and island attractions, making it well-suited for Siesta Key weekly rentals or extended stays. brbrExperience a truly unique Siesta Key vacation home with pool at Sundown Sanctuary, where mid-century architecture meets tropical tranquility. From the Zen garden and private guesthouse to the sun-drenched courtyard and elegant interiors, every detail is designed for relaxed island living. Book your stay with Siesta Key Luxury Rental Properties today and discover one of Siesta Key’s most distinctive coastal retreats! brbr- brThis home is managed by Siesta Key Luxury Rental Properties. brbrThis home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted.brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr4 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. brbrWe 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. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. 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.

Sundown Sanctuary! Modern home near the north end of Siesta Key!

Siesta Key, Florida, United States

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Sleeps

$398.12

Prepare to embark on an unforgettable beach escapade at Siesta Key Beach, the epitome of all beaches, with its sparkling quartz sand and stunning sunset views. Nestled away on the third is the ultimate luxurious hideaway, Unit 3C. With two bedrooms, two full bathrooms, and 1220 sq. ft. of living space, you'll experience an opulent lifestyle.brbrThe beach is just a short walk away, and the lanai and bedroom offer breathtaking views of the Gulf. The Master Bedroom features 2 Queen Beds, while the guest room has an additional queen.brbrThe Kitchen is equipped with full-sized appliances, a kitchen island for social gatherings, 3 TVs, and Free WIFI.brbrWe cater to all your beach needs, providing beach towels and chairs, allowing you to enjoy your time at the beach to the fullest. And after a day of fun, take a dip in the heated pool, fire up the BBQ grill, or work out in the gym. You can even challenge your friends to a game of shuffleboard on the court available for guests.brbrLocated in the heart of Siesta Key, the Village is just a short ride away on the free trolley, offering a variety of restaurants, nightlife, and shopping. And the cherry on top The enclosed lanai provides panoramic Gulf views, displaying some of the world's most beautiful sunsets.brbrOur onsite team at Crescent Royale is eager to assist you, ensuring you have the best vacation experience. So, pack your bags and book your stay today - paradise awaits you at Siesta Key!

Steps to the Beach 2 Bed 2 Bath at Siesta Key Beach with Full Gulf Views

Siesta Key, Florida, United States

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Bath

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$283.25

Prepare to be whisked away to a beachy paradise penthouse Condo 508 in stunning Siesta Key Beach! This top-floor one-bedroom unit offers up a whopping 820 square feet of pure relaxation and cozy comfort. With Gulf and beach views that'll make your heart skip a beat, you'll be feeling like a brand new person in no time.brbrThe master bedroom boasts a king-sized bed that's guaranteed to give you the best sleep of your life, and there's a sofa sleeper available for any extra guests. You won't have any trouble staying entertained with two TVs, free WIFI, and basic cable.brbrThe kitchen is fully equipped for all your culinary needs, and extras like towels, linens, beach chairs, and umbrellas are all provided so you can enjoy the beach to the fullest.brbrSpeaking of the beach, it's only 100 steps away and offers up soft white sand and stunning Gulf sunsets that you can admire from the comfort of the screened lanai or while lounging on the beach.brbrOnce the sun starts to set, treat yourself to a glass of wine on the screened-in lanai and watch the sky transform into a painting. And for those looking for a bit more excitement, Siesta Key Village is just a short trolley ride away, offering up a plethora of dining, shopping, and nightlife options.brbrThe condo complex has a heated pool and an on-site gym for all the fitness gurus out there. Our team is dedicated to making sure your stay is both carefree and enjoyable.brbrDon't wait another second to book your beach vacation at Condo 508! This dreamy spot won't be available for long, so reserve your spot now!

Incredible Siesta Key Beach Gulf Views 1 Bed 1 Bath Top Floor Steps to Beach

Siesta Key, Florida, United States

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