
Waterfront holiday rentals in Siesta Key
Find and book unique waterfront rentals on Airbnb
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

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.

Sea Club II Garden House
This surprisingly spacious 1200sf beach bungalow has been completely renovated in February 2020 from floor to ceiling. You will enjoy 3 spacious bedrooms with a private Master suite, spacious updated eat in kitchen and large family room. The unit is unique with a private deck to relax on at night. Walking distance to private beach access as well as a newly renovated heated salt water Community pool (Shared) on the intercoastal with breath taking views. This is a one of a kind experience.

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: Open Sun, $150/nt + Fees!
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.

Siesta Key Beach Front Condo
Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 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! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

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!
Popular amenities for waterfront rentals in Siesta Key
Waterfront apartment rentals

Beachfront Corner Condo | Sunset Gulf Views

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

Wave Whisper in Siesta Key

Cozy Condo in Siesta key with boat dock

Serenity on the Manatee
Waterfront house rentals

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

Beachfront Getaway in Siesta Key

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

Luxury Waterfront Home in Sarasota w/ Pool & Dock

Bayfront Beach access with Heated Pool!

Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub

Heated Pool, Elevator, Waterfront, Fire Pit, Dock

Beachfront 180-Degree View, Walk to Village!
Waterfront apartment rentals

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

The Beach Condo #107 Beachfront Full View

Siesta Key For Me @ The Palm Bay Club

KING Bed + Anna Maria Island Beaches + Beach Gear!

Sunset and beach view from your balcony Unit 403

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Siesta Key Beach (OHAB) Townhouse #1 beach

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £196 | £258 | £304 | £249 | £190 | £189 | £198 | £170 | £154 | £162 | £177 | £199 |
| 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 holiday rentals
Explore 510 holiday rentals in Siesta Key

Nightly prices starting at
Siesta Key holiday rentals start at £88 per night before taxes and fees

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

Family-friendly holiday rentals
410 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 70 rentals that welcome pets

Holiday rentals with a pool
460 properties feature pools

Rentals with dedicated workspaces
230 properties have a dedicated workspace

Wifi availability
510 of Siesta Key holiday rentals include wifi 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!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Flat rentals Siesta Key
- Rentals with outdoor seating Siesta Key
- Family-friendly rentals Siesta Key
- Rentals with lake access Siesta Key
- Beachfront rentals Siesta Key
- Fitness-friendly rentals Siesta Key
- Rentals with an EV charger Siesta Key
- Beach apartment rentals Siesta Key
- Bungalow rentals Siesta Key
- Rentals with a patio Siesta Key
- Pet-friendly rentals Siesta Key
- Rentals with a washing machine and dryer Siesta Key
- Beach house rentals Siesta Key
- Rentals with pools Siesta Key
- House rentals Siesta Key
- Rentals with beach access Siesta Key
- Apartment rentals Siesta Key
- Rentals with a sauna Siesta Key
- Mansion rentals Siesta Key
- Rentals with a firepit Siesta Key
- Rentals with a hot tub Siesta Key
- Rentals with a fireplace Siesta Key
- Cottage rentals Siesta Key
- Townhouse rentals Siesta Key
- Luxury rentals Siesta Key
- Rentals with breakfast Siesta Key
- Villa rentals Siesta Key
- Rentals with a kayak Siesta Key
- Waterfront rentals Sarasota County
- Waterfront rentals Florida
- Waterfront rentals United States
- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Coquina Beach
- Turtle Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Caspersen Beach
- Tampa Convention Center
- Cortez Beach
- St Pete Beach
- Jannus Live
- Anna Maria Public Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- Englewood Beach
- North Beach At Fort DeSoto Park
- Tropicana Field
- Splash Harbour Water Park





