Vacation Rentals By Owner In Siesta Key, FL

$381.51

Stunning Bay Views & Steps to Siesta Key Beach - Harbor Towers 514

Siesta Key, Florida, United States

Harbor Towers – 514 by Tropical Sands Accommodations brCondo in Siesta Key, Florida brbrDiscover your perfect couples escape at Harbor Towers 514! This 5th-floor condo offers breathtaking bay views and is just a short 7-minute walk to the pristine sands of Siesta Key Beach. brbrHighlights br• 7-minute walk to the beach br• 2-minute walk to Siesta Key Breeze Trolley stop br• Screened-in lanai br• Two heated community pools br•Three community tennis courts br• Fitness center, BBQ Area, and Marina br•13-night minimum stay community and 1 parking spot brbrCommunity Amenities: brThis complex features two heated pools, three tennis courts, a fitness center, a grilling patio, and a Marina (Additional fee, registration, and documentation required). brbrInside Space: brWith a screened-in lanai, cozy living space, kitchen, and a complete bedroom and bath, you’ll feel right at home! brbrRoom Details br-Primary Bedroom: Two Queen beds br- Living Room: Full Sleeper Sofa brbrLocal Attractions Await:brYour home away from home features a cozy living area, a well-equipped kitchen, a complete bedroom, and a bath. The screened-in lanai offers a perfect getaway to unwind.brbrBook Your Stay Today!brDon’t miss your chance to create cherished memories in paradise. Reserve Harbor Towers 514 now and immerse yourself in the ultimate Siesta Key experience!

2

Bed

1

Bath

6

Sleeps

$336.21

/ Nightly

Apartment

Urban 2 Bed 2 Bath Condo - Perfect stay while exploring Orlando,Florida

Siesta Key, Florida, United States

GRH759931 - The Anchorage - 2 Bed 2 Baths Condo:brWelcome to your home away from home!brbrbrbrNestled in the heart of Siesta Key, our two-bedroom, two-bathroom condo invites you to step into a world of comfort and relaxation. As you step inside, sleek decor surround you, beckoning you to kick off your shoes and put your feet up.brbrbrbrThe fully-equipped kitchen is a chef’s dream, boasting all the tools you need to whip up your favorite meal. As you cook, the aroma of fresh herbs and spices fills the air, making your mouth water in anticipation.brbrbrbrThe dining room and living room flow seamlessly together, creating a bright and airy space perfect for entertaining or simply lounging with your loved ones. Vibrant hues and plush textures create a sense of warmth and coziness, making you feel instantly at home.brbrbrbrThe primary bedroom is a sanctuary unto itself, When morning comes, you can step out onto the balcony and savor a cup of coffee while taking in the breathtaking views of the Intracoastal waterway.brbrbrbrThe second bedroom is just as welcoming, As you climb into bed, the sense of comfort and security surrounds you, enfolding you in a cocoon of tranquility.brbrbrbrBoth bedrooms offer access to the balcony, where you can spend lazy afternoons soaking up the sun and drinking in the stunning scenery.brbrbrbrThe Anchorage is the perfect place to make the most of your stay on Siesta Key. Private beach access, an Olympic-size heated pool, tennis and pickleball courts, shuffleboard, cornhole, fishing, walking trail, picnic, large BBQ grills, and more await you! Additionally, if you decide to bring your boat, the large boat dock is a convenient bonus.brbrbrbrAnd if you're in the mood for some island fun, you won't have to go far. Stroll to nearby restaurants, bars, and shopping centers. Or jump on the free Siesta Key Trolley and take a short ride to The Village where you'll find even more things to do. The possibilities are endless on this beautiful island.brbrbrbrThis is more than just a place to stay. It’s a place where memories are made, where families come together, and where dreams come true. We invite you to make our condo your own: to savor the beauty, the tranquility, and the joy of Siesta Key.brbrbrbrWelcome home. For your convenience, there is an onsite coin-operated washers and dryers on each floor.brbrbrbrTo make your arrival a little easier on you, our starter welcome packet includes:brbr1 Paper Towelbrbr1 Pack Dishwasher Detergentbrbr1 Sm Bottle Dish Soapbrbr2 Rolls Toilet Paperbrbr4 Bars of SoapbrbrAny supplies beyond this are up to the guest to stock and replenish, we do not restock these items.brbrThis is an industry-standard practice.brbrNo salt/pepper or cleaning supplies are stocked due to safety issues.brbrbrbrGuest must be 25 and up to rent this condo.brbrbrbrJanuary 1 until April 16, 2023brbrper HOA rules only Saturday to Saturday stay is allowed.brbrNo other departure or arrival date can be accommodated.brbrDates outside of those listed above we can accommodate different arrival and departure dates.brbrbrbrAdditional Info:brbr* Free access to all resort amenitiesbrbr* Free on-site parkingbrbr* Smoke-free and pet-free for your comfortbrbr* Towels and linens are providedbrbr* Complimentary wireless internetbrbrSleeping Arrangements:brBEDROOMS (Sixth Floor Condo)brbrBedroom 1: One King BedroombrbrBedroom 2: Two Queen BedroombrbrThe Anchorage:brGuests staying at The Anchorage on Siesta Key have access to America’s #1 beach.brEasily 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.brPools, walking trails, and sports courts are ready for you to use during your vacation. Pack a picnic and you’ll be at the beach in just minutes. Book your stay at this home and begin living the vacation you deserve!brbr Sweet Home Vacation:brWe are a professional Vacation Home Rental Agency with over 14 years of experience In the Orlando, Florida area. Your safety and comfort Is our top priority, and all of our homes are cleaned with enhanced safety and cleaning methods. No check-In is required as you may go directly to the home with the provided access code. If you have any questions, our reservation team at Sweet Home Vacation is available to help you 7 days a week. We can also help you locate car rentals and tickets for Orlando's famous attractions. Whether this is your first time, or you are a returning guest, we will make sure you have an amazing trip. brbrBook now or send us your inquiry. We are looking forward to accommodating you!

2

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2

Bath

6

Sleeps

$343.03

/ Nightly

Condo

Beachfront Condo with Unobstructed Gulf Views – Steps to the Sand

Siesta Key, Florida, United States

Welcome to Fisherman’s Cove, a rare waterfront property perfectly positioned between the Gulf of Mexico and Blind Pass Lagoon. Located at 8900 Blind Pass Road on the quiet south end of Siesta Key, this ground-floor condo offers unobstructed Gulf views and direct beach access — you simply step outside, and you’re on the sand.brbrStart your mornings with coffee overlooking the water and end your evenings with breathtaking sunsets right from your private terrace. You truly can’t get closer to the beach.brbrWhy Guests Love This Condo:brbrUnobstructed views of the Gulf of MexicobrbrGround-floor unit – walk straight onto the beachbrbrPrivate terrace perfect for sunset viewsbrbrQuiet, peaceful south end of Siesta KeybrbrGated beachfront communitybrbrFishing from both the Gulf and Blind Pass LagoonbrbrFree boat docks availablebrbrGreat for kayaking and paddleboardingbrbrWalking distance to Turtle BeachbrbrEasy access to restaurants and shopsbrbrFisherman’s Cove is ideal for outdoor lovers. Fish directly from the shoreline or the lagoon, launch a kayak or paddleboard, or bring your boat and take advantage of the free boat docks (off-site trailer storage required; local options available through the office).brbrNext door is Turtle Beach, known for swimming, shelling, and its picnic and grilling areas. The community is tucked away behind Turtle Beach, creating a peaceful setting away from the crowds.brbrFor dining and entertainment, several restaurants are within walking distance. Crescent Beach is just 2.5 miles away for groceries and additional dining, and Siesta Key Village is about 7 miles north, offering lively nightlife, shopping, and more restaurants. Downtown Sarasota is just a short drive away with even more options.brbrDuring your stay, be sure to visit nearby Siesta Beach, famous for its cool, powdery white sand made of nearly pure quartz — often ranked among the best beaches in the world.brbrSleeping Arrangements - Comfortable sleeping options make this unit ideal for families or groups.brPrimary Bedroom: King bed, private en-suite bathbrGuest Bedroom: One Queen and One Twin brLiving Room; Sleeper Sofa

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$1594.41

/ Nightly

Condo

Lulu's Key House: Private Heated Pool, Steps to Siesta Key Beach & Perfectly Located in the Village!

Siesta Key, Florida, United States

Welcome to Lulu’s Key House—your ideal group getaway on Siesta Key! brbr brbrPerfect for large families or groups, this rare 4-unit Siesta Key property offers the ideal setup—stay close together while enjoying the privacy of separate updated units. Just a 2-minute walk to Siesta Key Beach and steps from the Village, this 6-bedroom, 6-bath coastal compound sleeps up to 20 guests comfortably. Book the entire property for the ultimate group getaway with shared outdoor spaces and private retreats for downtime! brbr brbrLOCATION HIGHLIGHTS: brbr- Located directly in Siesta Key Village – Walk to shops, dining, and nightlife brbr- 2-minute walk to Siesta Key Beach – Powdery white sand and turquoise water brbr- Island shuttle transportation available – No need for a car once you arrive brbr- Steps to entertainment but tucked just enough for privacy brbr brbrPROPERTY FEATURES: brbr- 4 private units combined into one group stay experience brbr- 6 bedrooms, 6 full bathrooms – 4 master suites for comfort brbr- Sleeps up to 20 guests brbr- Private entrances for each unit – Perfect for families and friends traveling together brbr- Coastal décor and upgraded finishes throughout brbr- 4 fully stocked kitchens and 2 balcony spaces for lounging brbr- 10 HDTVs and free WiFi included brbr- 2 washers and 2 dryers on-site brbr brbrOUTDOOR SPACES: brbr- Private heated courtyard pool – Open year-round brbr- Outdoor lounge seating and café umbrellas brbr- Gas grill with dining area for casual island meals brbr brbrKITCHEN & DINING: brbr- 4 modern kitchens with full appliances brbr- Regular and Keurig coffee makers provided brbr- Dishwashers, cookware, utensils, and dining essentials included brbr- Indoor and outdoor dining options for group gatherings brbr brbrBEDROOMS AND BATHROOMS: brbr- 4 master bedrooms with en-suite bathrooms brbr- 2 King bedrooms and 4 Queen bedrooms brbr- 4 Queen sleeper sofas with linens provided brbr brbrEXTRA PERKS: brbr- Beach towels, chairs, umbrellas and caddy ready to go brbr- Starter pack of toiletries available brbr brbrLOCAL FAVORITES: brbr- Siesta Key Beach for sunsets, shelling, and swimming brbr- Siesta Village nightlife, live music, seafood spots, and coffee shops brbr- Easy access to kayak rentals, parasailing, and island tours brbr- Bike and scooter rentals just around the corner brbr brbrIMPORTANT INFO: brbr- No smoking and no pets permitted brbr- Pool depth is 5 ft at deep end brbr- 6 parking spots included with stay brbr brbrEXPERIENCE COMFORT, CONVENIENCE, AND A GETAWAY LIKE NO OTHER! BOOK YOUR STAY TODAY!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.

6

Bed

6

Bath

20

Sleeps

$534.33

/ Nightly

Condo

Siesta Beach Front Suite

Siesta Key, Florida, United States

A beach view with private beach access at Siesta Beach Front Suite will create memories that last a lifetime! Enjoy this beachfront home with direct beach access. This location will wow you! Nestled in a 7 unit private beach front location, you will enjoy the very private beach experience few can imagine. This ground floor unit gives you beach access and beach vibes plus, it's an easy 3 block walk to Siesta Village. Park at your front door and walk to the #1 beach in America out your back door!

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Sleeps

$261.82

/ Nightly

Condo

2 bedroom condo across from #1 Rated Siesta Key Beach

Siesta Key, Florida, United States

2/2 newly renovated Ground Floor Condo with outdoor private patio across from Siesta Key public beach. Walking distance to Siesta Village or utilize the “Siesta Breeze” Trolley to get around the Island.

2

Bed

2

Bath

5

Sleeps

$455.71

/ Nightly

Condo

AMAZING OCEAN VIEWS! ON THE BEACH! COMPLETELY RENOVATED!

Siesta Key, Florida, United States

AMAZING OCEAN VIEWS. POWDERY WHITE SAND. PRIVATE BEACH. WALKING DISTANCE TO RESTAURANTS/BARS/SHOPS. RECENTLY RENOVATED.brbrLUXURY BEACHFRONT CONDO AVAILABLE in Whispering Sands, Siesta Key starting June 2026!brbrBreathtaking sunsets & more await in this well-appointed unit featuring a luxury renovation with ALL the upgrades. It overlooks the sugar sand and crystal clear waters of Siesta Key Beach with panoramic views from multiple rooms! The open concept space boasts a custom kitchen with high end appliances and is stocked with the essentials. The living room & master bedroom have romantic fireplaces & an inviting beachy-chic style perfect for a getaway! The beachfront condo has direct access to the pool and beach, covered parking, and lots more!brbrFeatures:br- 2 bed/ 2 bathbr- brand new appliancesbr- private access to the heart of Siesta Key Village (ample shops, restaurants, entertainment within yards of the private pedestrian gate)br- private white sand beach br- large balcony with unobstructed beachfront viewbr- beachfront poolbr- free use of kayaks and paddle boardsbr- turnkey furnishedbr- much more! brbrRequirements:br- One renter must be 55+br- No Smokingbr- No Pets (Sorry)

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Sleeps

$312.64

/ Nightly

Condo

Across the Street to Siesta Key Beach, Tennis. Pickleball, Park, Heated Pool | Waterfront Balcony!

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Our House at the Beach Turtle Gate! brbr brbrEnjoy your stay across from the #1 rated Siesta Key Beach at Our House at the Beach. This newly updated townhome features an expanded balcony with pond and fountain views, where turtles often wander by. Beach gear is provided, so you can spend your days relaxing on the sand or enjoying water adventures nearby. brbr brbrLOCATION HIGHLIGHTS: brbr- Directly across from street from the main entrance to Siesta Key Beach brbr- Public beach amenities: bathrooms, concession stand, volleyball courts, playground, pickleball/tennis courts brbr- 1.1 miles from Siesta Key Village brbr- Free Siesta Breeze Trolley, or local free rides brbr- Heated communal pool, grills brbr- Tennis courts/pickleball, bike racks brbr- Golf carts welcome brbr brbrPROPERTY FEATURES: brbr- 2 Bedroom/ 2 bathroom townhouse condo (over 1352 sq ft) brbr- Access via stairs brbr- Garage access/parking brbr- Dedicated WIFI and cable brbr- Self check in provided brbr- Central A/C with ceiling fans brbr- Private washer and dryer, linens and towels provided brbr brbrLIVING ROOM: brbr- Large, open space with expanded sliding doors and coastal decor brbr- Access to private balcony with pond and landscape views brbr- Large smart TV with cable included brbr brbrKITCHEN AND DINING: brbr- Modern kitchen with stainless steel appliances and solid stone counters brbr- Fully stocked with pots, pans, dishes, utensils brbr- Dining table for 6 brbr- Café table for 2 off the kitchen brbr- Sliding doors with views of the tennis courts. brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Bedroom: main level, king bed, Smart TV, en-suite bathroom, 2 closets, water views brbr- Guest Bedroom: upper level, 2 twin beds, Smart TV, sliding doors with tennis court views, closets. brbr- Master ensuite bathroom: his & her sinks, tiled walk-in shower (note: pocket door does not close fully) brbr-Guest bathroom: tub/shower combo with glass door brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, beach umbrella, and beach towels brbr brbrNEARBY FAVORITES: brbr- Daquiri Deck, Siesta Key Oyster Bar, Another Broken Egg, Old Salty Dog brbr- Siesta Market, Beach Club, Big Tiki Lounge brbr brbrIMPORTANT INFO: brbr- No pets allowed brbr- No smoking brbr- Parking restrictions: No boats, trailers, motorcycles, oversized or commercial vehicles allowed brbr brbrWHETHER A WEEK AWAY OR AN EXTENDED STAY, THIS PROPERTY HAS EVERYTHING YOU NEED, BOOK TODAY!brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

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Sleeps

$797.56

/ Nightly

Private Vacation Home

Silver Shore | Unit w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Siesta Key, Florida, United States

Silver Shore | Modern Escape, Rooftop Deck, Pool & Across from Siesta Key Beachbrbr Why You'll Love This HomebrFrom morning coffee on the rooftop to sunset dips in your private heated pool, Silver Shore invites you to unwind in total comfort. Spacious enough for large families or groups, this upscale retreat offers elevator access, beach proximity, and modern style—all in one beautifully designed unit which is apart of a shared duplex.brbr ‍ ‍ Perfect ForbrPerfect for multigenerational families or groups seeking luxury, space, and easy access to Siesta Key Beach and Village—all with bonus rooftop views!brbr ️ Imagine ThisbrThe open-concept layout welcomes you with designer furnishings, sleek finishes, and a kitchen that's made for group feasts and late-night snacks. As the kids scatter to the bunk room and adults claim their king suites, the home hums with anticipation.brbrOutdoors, your private backyard and heated pool offer space to lounge, splash, or grill. When the day slows, head to the shared rooftop lookout—wine in hand—to soak in panoramic island views as dusk paints the Gulf in coral tones. Then retreat to your serene bedrooms, where high-end beds and blackout shades promise deep, restful sleep before another beach-filled day.brbr Where You'll Sleepbr- Bedroom 1: King Bed, Ensuite Bath, Upper Floor, TVbr- Bedroom 2: King Bed, Shared Bath, Upper Floor, TVbr- Bedroom 3: Two Full Over Full Bunk Beds, Shared Bath, Upper Floor, TVbrbr Explore the Areabr- 0.1 miles to Siesta Key Public Beach Accessbr- 0.6 miles to Siesta Key Village – shops, fresh seafood, nightlife & boutiquesbr- Walkable, bike-friendly neighborhood with island energybr- Kayak, bike, or paddle board rentals available nearbybrbr Your Siesta Key Escape AwaitsbrSilver Shore blends modern comfort with unbeatable beach access—plus a rooftop deck that's hard to top. Book now and arrive knowing your home has been meticulously cleaned under our CottageClean™ program, including a 6-hour deep clean and 35-point inspection before each guest's arrival.brbr Need to Know: This unit is one side of a duplex. Guests will have private access to the right-side garage, a private backyard and pool area, the entire fourth floor, and the right side of the third floor. The third floor is divided by a wall, providing a fully private space on your side. A shared exterior spiral staircase leads to the shared rooftop deck, which may be accessed by guests of the neighboring unit. Please contact us if you have any questions about the layout of this duplex. Starter Supplies: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. Heated Pool: Heated from November 15 – April 15. This home has stairs and an elevator. Please contact us if any guest has mobility concerns.brbr• Related Units: Looking for more space or options Book other units in the same building:br • 6 Bedroom Option: Beach Dreambr • 3 Bedroom Option: Crystal Sands

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Bath

Sleeps

$768.69

/ Nightly

Private Vacation Home

Crystal Sands | Home w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Siesta Key, Florida, United States

Crystal Sands | Steps to the Sand Rooftop Sunset Views & Modern Poolside Escapebrbr Why You'll Love This HomebrJust 2 minutes from Siesta Key Beach, Crystal Sands delivers modern style, a private heated pool, and a rooftop lookout deck for golden-hour views. It's everything you love about coastal living!brbr ‍ ‍ Perfect ForbrGreat for beach-loving families or groups seeking a sleek, central home base close to the sand and Siesta Key Village—plus extra savings while work happens next door.brbr ️ Imagine ThisbrStart your morning with a stroll to the beach—just 0.1 miles away—your feet already in the powder-soft sand before coffee's gone cold. After a sun-filled day, return to your fully private backyard to lounge by the heated pool or fire up the grill. The open-concept interior welcomes you with natural light, modern coastal furnishings, and an all-white kitchen made for family-style meals.brUnwind upstairs in one of three spacious bedrooms with plush king beds and a fun full-over-full bunk setup, ideal for kids or cousins sharing laughs into the night. As the sun begins to set, head up to the shared rooftop deck, drink in hand, and soak in panoramic views of the Gulf skies. Then wind down with a movie, a dip in the pool, or a moonlit toast on your private patio.brbr Where You'll Sleepbr- Bedroom 1: King Bed, Ensuite Bath, 2nd Floor, TVbr- Bedroom 2: King Bed, Shared Bath, 2nd Floor, TVbr- Bedroom 3: Full Over Full Bunk Bed & Full Bed, Shared Bath, 2nd Floor, TVbrbr Explore the Areabr- 0.1 miles to Siesta Key Public Beach Accessbr- 0.6 miles to Siesta Key Village – walkable shops, restaurants, and nightlifebr- Rent paddle boards, kayaks, or bikes nearby for outdoor adventuresbr- Enjoy a laid-back, residential beachside neighborhoodbrbr Your Siesta Key Escape AwaitsbrCrystal Sands fills quickly thanks to its unbeatable beach access, rooftop sunset views, and modern design. Our CottageClean™ program ensures a spotless stay with a six-hour deep cleaning and 35-point inspection before each arrival—giving you peace of mind and a pristine welcome.brbr Need to Know: This unit is one side of a duplex. Guests will have private access to the left-side garage, a private backyard and pool area, the entire second floor, and the left side of the third floor. The third floor is divided by a wall, providing a fully private space on your side. A shared exterior spiral staircase leads to the shared rooftop deck, which may be accessed by guests of the neighboring unit. Please contact us if you have any questions about the layout of this duplex. Starter Supplies: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. Heated Pool: Heated from November 15 – April 15. This home has stairs and an elevator. Please contact us if any guest has mobility concerns.brbr• Related Units: Looking for more space This home is part of a duplex with other bookable options:br • 6 Bedroom Option: Beach Dreambr • 3 Bedroom Option: Silver Shore

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Bath

Sleeps

$1602.66

/ Nightly

Private Vacation Home

Beach Dream | Home w/ Ocean Views, 2 Private Pools, Rooftop Lookout and Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Beach Dream | 6BR with Rooftop Patio, Two Private Heated Pools, and a 2-Min Walk to Siesta Key Beachbrbr Why You'll Love This HomebrWelcome to Beach Dream, a luxurious 6-bedroom entire duplex offering dual private pools, a rooftop lookout, and a prime location to Siesta Key Beach just across the street. With modern interiors, sleeping for up to 22 guests, it's the perfect space for reunions, retreats, and unforgettable coastal gatherings.brbr ‍ ‍ Perfect ForbrIdeal for large families, multi-generational groups, wedding parties, or friends traveling together—Beach Dream gives you the privacy of two units with the shared benefits of rooftop sunsets and unbeatable walkability to the beach and village.brbr ️ Imagine ThisbrWake up just steps from the sand, where two fully private heated pools await your crew's morning splash. Each part of this stylish duplex boasts its own modern living space, full kitchen, and designer bedrooms, giving your group the ability to gather together while also spreading out when needed. Prepare meals in either sleek kitchen, or host a group dinner al fresco on the patios. Spend afternoons lounging in one of the two fenced backyards or sipping cocktails on the shared rooftop lookout, with panoramic views of Siesta Key's shimmering Gulf waters. With dual laundry rooms and TVs in every bedroom, Beach Dream is both functional and fabulous for group living. As night falls, retreat to one of six beautifully appointed bedrooms, including four with king beds and two expansive bunk rooms that sleep up to 14 combined. Whether you're planning lazy beach days or lively evenings in Siesta Key Village, Beach Dream is the elevated group escape you've been dreaming of.brbr Where You'll SleepbrCrystal Sands:br• Bedroom 1: King Bed, Ensuite Bath, 2nd Floor, TVbr• Bedroom 2: King Bed, Shared Bath, 2nd Floor, TVbr• Bedroom 3: Full Over Full Bunk Bed & Full Bed, Shared Bath, 2nd Floor, TVbrbrSilver Shorebr• Bedroom 4: King Bed, Ensuite Bath, 4th Floor, TVbr• Bedroom 5: King Bed, Shared Bath, 4th Floor, TVbr• Bedroom 6: Two Full Over Full Bunk Beds, Shared Bath, 4th Floor, TVbrbr Explore the Areabr• 0.1 miles to Siesta Key Public Beach Accessbr• 0.6 miles to Siesta Key Village – a short walk to dining, boutiques, and nightlifebr• Rent kayaks, paddle boards, and bikes nearbybr• Enjoy local cafés, sunset bars, and family activities all within easy reachbrbr Your Siesta Key Escape AwaitsbrA rare find for large groups, Beach Dream offers two duplex homes, two pools, and a rooftop deck just a 2-minute walk to the beach. Your stay includes our trusted CottageClean™ program—a deep, 6-hour clean and 35-point inspection before every guest. Now is the time to book your dream group getaway!brbrNeed to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. Both pools are heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. Stairs: Both units have stairs. Contact us if any guest has mobility concerns. Duplex Note: This listing includes both duplex units. Guests will have access to the entire unit, including both private pools and backyards. brbrRelated Units: Prefer to book just one part of the duplex View individual listings:br • 3 Bedroom Option: Crystal Sandsbr • 3 Bedroom Option: Silver Shore

Bed

Bath

Sleeps

$387.55

/ Nightly

Private Vacation Home

Pink Flamingo | Old Florida Charm on Siesta Key, Private Pool, Dog-Friendly

Siesta Key, Florida, United States

Escape to Pink Flamingo, a charming 3-bedroom, 2-bathroom dog-friendly house on Siesta Key, where Old Florida charm meets modern comfort. Nestled under a stunning Banyan tree, this delightful home offers a lush, private yard featuring your very own pool and spa (pool heat available for an extra fee!). Inside, discover a true Old Florida cottage feel with an open-concept layout that invites relaxation. The nicely updated, fully equipped kitchen and gas grill are ready for your vacation feasts. Unwind in the cozy front living room, or find your ultimate retreat in the primary bedroom, secluded at the back for privacy, featuring a king bed, a dedicated office space for remote work, and direct access to a serene screened-in porch. The two additional bedrooms each feature a double bed, ensuring comfort and privacy for everyone. You're perfectly situated on a quiet street, just a short stroll to North Village's vibrant shops, restaurants, and mere moments from the world-famous Siesta Key Beach. Come experience why this unique gem is a favorite, offering the best of Siesta Key right at your doorstep! brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: We're delighted to welcome your furry family members! This property is pet-friendly, and a non-refundable pet fee (per pet) will be applied after booking and must be paid prior to check-in. Please feel free to inquire about the specific pet policy applicable to your reservation.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

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Bath

Sleeps

$177.05

/ Nightly

Condo

Turquoise Turtle | Condo w/ Beach Views + Resort Amenities, Pool and Marina

Siesta Key, Florida, United States

Discover Turquoise Turtle, a beautiful 2-bedroom, 2-bathroom condo nestled within the luxurious Harbor Towers Yacht & Racquet Club on Siesta Key. This charming beach palace is your true coastal getaway, offering a prime location and resort-style amenities. From the moment you park in your assigned spot, you'll feel the resort vibe. Step into the beautifully remodeled lobby and take the elevator to the fourth floor, where the inviting blue hues of Turquoise Turtle welcome you to paradise. Inside, you'll find modern beach decor and an updated galley kitchen, designed for your comfort. The primary bedroom features a king-sized bed, while the second bedroom offers a comfortable queen bed. A sleeper sofa in the living area accommodates two additional guests, allowing the condo to comfortably sleep up to 6 people. The two bathrooms are clean and functional, and the split floor plan ensures privacy for all guests. Step out onto your private balcony and enjoy views of the world-famous Siesta Key Beach directly across the street! You'll be just minutes away by foot, and a quick trolley, bike, or golf cart ride will take you to Siesta Key Village's delicious restaurants and vibrant shops. Harbor Towers boasts an array of amazing amenities, including two heated pools, three Har-Tru tennis courts, and an outdoor patio overlooking one of Siesta Key's largest marinas. Notably, the community is located directly on the Intracoastal Waterway, and for boat enthusiasts, you are able to register with the HOA to dock your boat right on-site. The community also offers convenient washers and dryers on every floor and a fitness room. Don't wait – book your ultimate Siesta Key vacation at Turquoise Turtle today!brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: To adhere to HOA guidelines, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

2

Bed

2

Bath

6

Sleeps

$201.78

/ Nightly

Condo

Two Tickets to Paradise |Beachfront condo w/ Private Beach Access + Amenities

Siesta Key, Florida, United States

Introducing your dream beachfront getaway in Siesta Key, Florida or as we like to call it... 2 Tickets to Paradise! This stunning 2-bedroom, 2-bathroom beachfront condo offers the perfect blend of luxury and relaxation. With direct beach access and tranquil views of the garden and ocean, it's the perfect spot to unwind. Step inside to discover a large kitchen, ideal for preparing meals and entertaining. The primary suite offers complete relaxation with a comfortable king-sized bed, a cozy spot to read a good book, and a large ensuite bathroom with a walk-in shower. Up to bringing friends or family There's plenty of room in the guest bedroom, offering two double beds and their own access to the guest bathroom. Did we mention paradise includes your own wet bar and wine fridge! Pour yourself a drink of your choice, walk over to watch the exquisite sunsets in the enclosed patio, and don't forget to open the sliding glass windows to let the cool ocean breeze in! Enjoy Gulf & Bay’s impressive amenities including 3 heated pools, 8 tennis courts, a fitness center, BBQ areas, and private access to Siesta Key Beach! You've waited so long, and now the wait is over, you've got 2 tickets to paradise! brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: To adhere to HOA guidelines, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

2

Bed

2

Bath

4

Sleeps

$306.39

/ Nightly

Condo

Mellow Mermaid | Pool & Close To SK South Village w/ Live Music & Restaurants

Siesta Key, Florida, United States

Welcome to your boho chic beach retreat located near the famous Crescent Beach on Siesta Key! This charming 2-bedroom, 2-bathroom condo comfortably sleeps 5, offering everything you need for a relaxing getaway. You'll feel right at home with a fully equipped kitchen for preparing your favorite meals and a cozy living room perfect for movie nights. Step out onto your screened lanai to relax with a good book – but don't forget, you're in Siesta Key! Enjoy sunny days by the community pool, or simply walk across the street to spend time playing or lounging on the soft sands of Crescent Beach. Searching for an unbeatable location You've found it! This retreat is nestled within Vista Hermosa, a quiet community with amazing walkability. Explore Point of Rocks beach access (Numbers 12 & 13), where you can snorkel, fish, swim, and hunt for unique shells. Plus, you can easily walk to Siesta Key's South Village, brimming with shops, restaurants, and entertainment, including the long-standing local favorite, Captain Curt's. Everything you need for a perfect beach vacation is right here. Book your unforgettable Siesta Key escape today! For larger groups, consider booking unit 210C, also managed by Ascendia Group, which can accommodate an additional 6 guests, allowing your whole family to enjoy this incredible destination together.brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: To adhere to HOA guidelines, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

Bed

Bath

Sleeps

$208.96

/ Nightly

Condo

Playing Hooky | Beachfront condo w/ resort-style amenities, Views of the Gulf

Siesta Key, Florida, United States

Ready to truly get away from it all Playing Hooky is your ideal retreat on the serene south end of Siesta Key, nestled within the fantastic Bay Tree Club community. This charming 2-bedroom, 2-bathroom condo offers spectacular views of the Gulf of America, showcasing those famous Siesta Key sunsets right from your balcony, which also overlooks the sparkling community pool. With convenient sliding doors, you can easily open up the screened balcony to fully embrace the gentle Gulf breezes. Inside, you'll find a primary bedroom with a queen bed and an additional bedroom featuring two twin beds, ensuring a comfortable night's sleep for everyone. While delightfully comfortable and perfectly set for relaxation, this gem provides everything you need to unwind and embrace vacation mode. The Bay Tree Club elevates your stay with resort-style amenities, including two heated community pools, a private beach, convenient car wash facilities, and even private fishing docks for the anglers in your group. Step outside and dive into an abundance of outdoor activities! Spend your days basking in the sunshine on the beach, exploring the mangroves by kayak, or simply sipping your favorite drink by the poolside. When you're ready for more adventure, hop on one of Siesta Key's FREE RIDES (like the Breeze Trolley) for an effortless trip up the island to the vibrant Siesta Key Village. There, you can indulge in boutique shopping, savor delicious dinners at award-winning restaurants, and enjoy lively entertainment with live music. It's time to truly Play Hooky in Siesta Key – your perfect blend of stunning views, fantastic amenities, and unforgettable island adventures awaits!brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: To adhere to HOA guidelines, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

Bed

Bath

Sleeps

$391.24

/ Nightly

Villa

Island House Beach Resort V36

Siesta Key, Florida, United States

House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twin beds and a sofa bed in the living area, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!brIsland

Bed

Bath

Sleeps

$377.4

/ Nightly

Condo

Eternal Sunshine | Beachfront Community w/ Pool - Steps to Siesta #1 Beach!

Siesta Key, Florida, United States

Indulge in the laid-back luxury of this beautifully remodeled condo at Crescent Arms, just steps from the pristine shores of Siesta Key Beach, named #1 in the USA! Recently updated with a new kitchen, bathrooms, and chic coastal decor, this vacation rental offers the perfect blend of comfort and style. Step out the door and sink your toes into the powdery white sands and crystal-clear Gulf waters that make Siesta Key famous. Inside, create culinary delights in the fully equipped kitchen, relax in the comfortable living room, and soak in partial beach views from your screened balcony. For those needing to stay connected, a dedicated workspace is located just off the kitchen. Both bedrooms offer ensuite bathrooms and balcony access: the primary suite features a king bed, and the second bedroom has two twin beds. Crescent Arms offers direct access to Siesta Key Beach and a community pool. Beyond the beach and pool, discover the vibrant Siesta Key Villages, both offering live music, shops, and restaurants (South Village - 0.5 mile, North Village - 2.5 miles), or explore the local scene in Gulf Gate (2 miles), known for its diverse dining and unique shops. Book your unforgettable Siesta Key escape today!brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! There are beach chairs available on the beach at the property and umbrellas available for rent.br• Pet Policy: To adhere to HOA guidelines, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

Bed

Bath

Sleeps

$415.15

/ Nightly

Private Vacation Home

Bikini Tini Time | Siesta Canal Home w/ Saltwater Pool & Sunset Martini Spot

Siesta Key, Florida, United States

Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously designed interior with thoughtful updates throughout, from the brand-new kitchen to the spa-like bathrooms. You'll find a designated office space off the kitchen, perfect for remote work. The first bedroom features a king bed, and the second bedroom features a queen bed. Outside, soak up the Florida sunshine by the sparkling saltwater pool. With direct canal access, cast a line for some fishing, or launch a paddle board and explore the tranquil canals, where you're likely to spot local manatees and other fascinating wildlife. After exploring the canals, take a leisurely walk of just a few minutes to the world-famous Siesta Key Beach. Feel the soft, powdery quartz sand between your toes and bask in the beauty of the Gulf. Then, it's back to your private oasis where, as the sun begins its descent, it's 'tini time! Mix your favorite martini and savor it while watching the spectacular sunset paint the sky over the canal, beautifully highlighting silhouetted palm trees. It's truly an unforgettable end to a perfect day! Bikini Tini Time offers the perfect blend of tranquility and convenience, just moments from Siesta Key Village's vibrant shops and restaurants. brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs and beach towels.br• Pet Policy: We're delighted to welcome your furry family members! This property is pet-friendly, and a non-refundable pet fee (per pet) will be applied after booking and must be paid prior to check-in. Please feel free to inquire about the specific pet policy applicable to your reservation.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

Bed

Bath

Sleeps

$558.77

/ Nightly

Private Vacation Home

Banyan Tree Beach House | Updated Canal-Front Pool Home w/ Private Dock

Siesta Key, Florida, United States

Are you ready to truly unwind under the majestic shade of a sprawling Banyan tree Imagine starting your day with a peaceful kayak paddle directly from your backyard, exploring the tranquil canal waters. Spectacular barely begins to describe this meticulously updated, canal-front pool home, designed for ultimate relaxation and fun. Step inside and feel the worries melt away as you discover an airy, open-concept floor plan, seamlessly flowing from one inviting space to the next. Every detail has been thoughtfully curated to reflect a chic, modern beach-style home, bathed in natural light and adorned with tasteful decor. The spacious living areas are perfect for gathering, while the fully equipped, chef-ready kitchen invites you to whip up vacation feasts or simply enjoy a morning coffee with a view. The luxurious primary bedroom is a true sanctuary, boasting views of the canal right from your king-sized bed. Wake up to the gentle sounds of the water, and with your private access to the refreshing pool and expansive patio, a morning dip is just steps away. The two additional, beautifully appointed bedrooms offer roomy comfort and privacy, each with ample closet space. One features a comfortable queen-sized bed, while the other provides two twin beds. These rooms are complemented by two additional, sparkling bathrooms, bringing the home's total to three well-appointed full bathrooms, ensuring ample convenience and a serene retreat for everyone. Outside, your private oasis awaits! The spacious patio is ideal for sunbathing, al fresco dining, or simply lounging by your sparkling pool. The highlight Your very own private dock, offering endless opportunities for fantastic fishing, or direct boating access to the shimmering Sarasota Bay and the vast Gulf of America! Imagine setting sail right from your doorstep. Please note that the garage is not available for guest use. When you're ready to venture out, convenience is key! Leave your car behind and enjoy a leisurely walk or bike ride to the vibrant Siesta Key Village. Here, you'll immerse yourself in a world of charming boutiques, delectable restaurants, and lively entertainment. Don't just dream about paradise – book it! It's all here, waiting for you to create unforgettable memories. The pool can be heated for an additional charge. brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: For the comfort of all our guests, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

3

Bed

3

Bath

6

Sleeps

Vacation Rentals By Owner In Siesta Key, FL

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$306.39

$208.96

$391.24

$377.4

$415.15

$558.77

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