
Waterfront vacation rentals in Siesta Key
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Siesta Key

Total vacation rentals
Explore 560 vacation rentals in Siesta Key

Nightly prices starting at
Siesta Key vacation rentals start at ﺩ.ﺇ 367 per night before taxes and fees

Verified guest reviews
Over 11,580 verified reviews to help you choose

Family-friendly vacation rentals
490 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Vacation rentals with a pool
530 properties feature pools

Rentals with dedicated workspaces
230 properties have a dedicated workspace

Wi-Fi availability
560 of Siesta Key vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Siesta Key rentals

4.8 Average rating
Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated waterfront rentals in Siesta Key
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
Welcome to our 3 Bedroom 2 Bathroom Siesta Key Beach House. Full kitchen. Walk to beach. We provide chairs & towels for the Beach Walk to Beach access #12 on Siesta key Lots of places to eat and drink, close by. Free WIFI Daily, Weekly rentals. Swimming Pool on site King Bed in Master bedroom, Bedroom 2 and 3 both have Queens This home is in a great location and it is only a short walk to shops , restaurants and Beach. This home has 2 x 1 bedroomed units attached and is great for families
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Crystal House on Siesta Key Beach
This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!
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NO Stairs, Siesta beachfront. Walk to the village!
Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.
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Beachwalk Townhouse with view of Gulf of Mexico
Townhouse with 1550 sq. ft. Private elevator, all new flooring, quartz countertops, sinks, faucets, shower. View of the Beach and Gulf of Mexico from Lanai and Master Bedroom. Only a few steps to Siesta Key Beach Heated Pool, garage, grill, all beach accessories. Relax on the lanai with a view of the beach/gulf or in the downstairs Florida room by the pool. Walking distance to the village of Siesta Key to the many restaurants and amenities. Have a relaxing stay on a wonderful island.
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Beach Bliss: Discounted August & September!
This sublime oceanfront studio condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the ground floor, overlooking the heated pool and ocean, this dreamy studio is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!
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Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!
Unwind in this spacious 4BR/2BA Siesta Key getaway, set on a quiet street steps from gated, private beach entry. Enjoy a resort-style shared pool when you're not at the shore, then head out to Siesta Key Village restaurants, shops, and the island's top attractions. ✔ 4 Bedrooms (Sleeps 10) ✔ Private Beach Access ✔ Open Design Living ✔ Renovated Chef's Kitchen ✔ Private Patio & Shared Outdoors (Pool, BBQ, Games, Fire Pit, Lounges) ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking Learn more below!
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@Shellmateisland |tiny home| island| bikes| kayaks
⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)
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Gulf Front! Sunset Deck! + Walk to Bridge St Pier!
🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.
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Private Beach with Loungers · 2 Pools & Bay View
Beachside resort life for families, groups and remote workers seeking easy beach access and active days. This oversized & Fully Renovated 2‑bed, 2‑bath condo sits in a gulf-to-bay complex so you can walk to the famed Siesta Key sand and hop the island trolley outside your door. Enjoy bay views, unwind in heated pools and the hot tub, use the on-site gym and courts, and take advantage of provided beach chairs, umbrella and wagon for effortless beach days.
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Siesta Key Quaint Beach House
This home, built in the 1950’s, has old Florida highlights including cypress wood walls and terrazzo floors located in a peaceful neighborhood. It is all on one level and sleeps 4 adults with a private patio including a gas grill. It’s only a 5 minute walk to Siesta Key beach and includes a beach cart, chairs, umbrella, towels and a cooler. Only a 10 minute walk or 2 minute ride to the village with shops, restaurants, music and nightlife.
BeachKitchenNearby

On the Beach; Siesta Key SunBum Studio
Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs.
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Siesta Key Oasis with Gulf Views
Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 5th floor unit has an extra large lanai that provides some of the best Gulf views on Siesta Key! 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year!
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Popular amenities for Siesta Key waterfront rentals
Waterfront apartment rentals

Just renovated, beach view from balcony Unit 203
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Newly Remodeled Beachfront Studio - On the sand!
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Sweet Retreat at Shorewalk!
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Las Palmas Beach Rentals Unit 1
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Longboat Key-OCEAN FRONT- on the beach
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Stylish Gray 2nd-Floor Condo w/ Heated Pool | 1BR
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New Modern on Beach Longboat Key (5 steps to Sand)
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Serenity on the Manatee
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Waterfront house rentals

Luxury 3B/3B waterfront home w/ pool + boat access
BeachOutdoor spacesFamily

Luxury Canal-Front Home + Heated Pool Near Beach
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Lake Front House with a Pool
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Rustic Sands - 650
BeachLocationQuiet

True Island Living House/beach/water views
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Beachfront 180-Degree View, Walk to Village!
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Siesta Bliss ~ Luxury Waterfront Retreat
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Spacious Home with Private Pool
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Waterfront condo rentals

Best Gulf Coast Condo w/Private Beach & Bay view
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Gulf Views | Walkable | Spacious
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The Beach Condo #107 Beachfront Full View
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Siesta Key For Me @ The Palm Bay Club
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Sarasota Surf & Racquet Club Siesta Key Condo
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★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
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Siesta Key condo, beach access, heated pool
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Beachfront Escape – Private Balcony, Gulf Views
ViewBeachHospitality
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,043 | ﺩ.ﺇ 1,414 | ﺩ.ﺇ 1,539 | ﺩ.ﺇ 1,315 | ﺩ.ﺇ 1,021 | ﺩ.ﺇ 1,138 | ﺩ.ﺇ 988 | ﺩ.ﺇ 848 | ﺩ.ﺇ 768 | ﺩ.ﺇ 808 | ﺩ.ﺇ 881 | ﺩ.ﺇ 992 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°C |
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