
Waterfront vacation rentals in Siesta Key
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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

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!

Summer House longboat key
Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

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.

Siesta Premier Location - The 'Calm of Siesta'
My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

Island Time!
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo 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...!

Siesta Key condo, beach access, heated pool
This condo is set in the perfect location between the beach and the bay! Soak up the sun at the heated pool, enjoy the tiki bar, or try your luck fishing on the pier, all while viewing the boats on the intercoastal! Included is private deeded beach access that is just a easy 5 min walk. Hop on the free trolley right outside your door to go to Siesta Key Village with plenty of restaurants, bars and shops only .5 miles away. 65" tv free wifi Netflix Disney+. Boat slip available up to 24'

Sarasota Surf & Racquet Club Siesta Key Condo
Our newly renovated condo is located on Siesta Key's award winning Crescent Beach. Our unit is has all of the amenities of home for your convenience. The primary bedroom has a king sized bed and its own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

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. If we are booked check out our additional units under our profile.

Palm Bay Club! Resort Living on Siesta Key!
Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

Beach, Village, Dock & Private Pool! One-of-a-kind
Rad’s Cozy Cottage – Siesta Key Private Home. Enjoy a heated saltwater pool, canal-front dock, and putting green at this one-of-a-kind tropical getaway. Steps from Siesta Village (shops, restaurants, nightlife) and the powdery-white sands of Siesta Key Beach. Fully updated 2BR/1.5BA cottage with modern kitchen, AC, Wi-Fi, and washer/dryer. Sleeps 6 (king + 2 twins + sofa). Book your island paradise!

Your DreamOasisAwaits: SiestaKeyEscape with Pool!
Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴
Popular amenities for Siesta Key waterfront rentals
Waterfront apartment rentals

Beachfront Corner Condo | Sunset Gulf Views

Condo Kokomo - stay ON the beach in Siesta Key!

Sweet Retreat at Shorewalk!

Pass a grille Gulf Way Beachfront Parking WiFi 13

Siesta Key - Poolside Suite - Studio - Free kayaks

Longboat Key-OCEAN FRONT- on the beach

Beachfront screened in lanai & hot tub, Gulf view

Wave Whisper in Siesta Key
Waterfront house rentals

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

NEW Saltwater Pool + Spa | Mins to AMI Beaches/IMG

Dockside Dream:Luxury canal front home, dock, pool

Walk to beach/village, boat lift, monthly discount

Experience "Old Florida" at the Coral Cottage

Top 1%, Waterfront, Elevator, Fishing, Firepit

Edgewater Escape - 454

Oceanfront home w/sunset views of Sarasota Bay
Waterfront condo rentals

Bayside Sunrise Cottage on Siesta Key!

The Beach Condo #107 Beachfront Full View

Siesta Key For Me @ The Palm Bay Club

KING Bed + Anna Maria Island Beaches + Beach Gear!

Lake View 1BR Condo | Heated Pool Near Siesta

Sunset and beach view from your balcony Unit 403

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Siesta Key Beach (OHAB) Townhouse #1 beach
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.ﺇ1,043 | ﺩ.ﺇ1,414 | ﺩ.ﺇ1,539 | ﺩ.ﺇ1,241 | ﺩ.ﺇ948 | ﺩ.ﺇ944 | ﺩ.ﺇ988 | ﺩ.ﺇ848 | ﺩ.ﺇ768 | ﺩ.ﺇ808 | ﺩ.ﺇ881 | ﺩ.ﺇ992 |
| 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 |
Quick stats about waterfront rentals in Siesta Key

Total vacation rentals
Explore 510 vacation rentals in Siesta Key

Nightly prices starting at
Siesta Key vacation rentals start at ﺩ.ﺇ441 per night before taxes and fees

Verified guest reviews
Over 12,500 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Vacation rentals with a pool
460 properties feature pools

Rentals with dedicated workspaces
230 properties have a dedicated workspace

Wi-Fi availability
510 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!
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