
Waterfront vacation rentals near Siesta Beach
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Top-rated waterfront rentals near Siesta Beach
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

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.

Sandy Toes & Sun Kissed Nose!
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...!

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!

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.

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.

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ heated pool, kayaks, table tennis & Tiki Hut. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

Newly Remodeled Beachfront Studio - On the sand!
ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

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 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.

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.
Popular amenities for waterfront rentals near Siesta Beach
Waterfront apartment rentals

Beachfront Corner Condo | Sunset Gulf Views

Condo Kokomo - stay ON the beach in Siesta Key!

Sweet Retreat at Shorewalk!

Across from #1 Siesta Beach & walk to town

Longboat Key-OCEAN FRONT- on the beach

Wave Whisper in Siesta Key

New Modern Longboat Key*5 Steps to Sand*Heatd Pool

Serenity on the Manatee
Waterfront house rentals

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

Beachfront Getaway in Siesta Key

Siesta Key Beach Getaway

Siesta Serenity ~ Pool/Waterslide/Waterfront

Summer House longboat key

Stylish & Bright: Steps to Beach ~ Pool ~ Hot Tub!

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!

Luxury Canal-Front Home + Heated Pool Near Beach
Waterfront condo rentals

Best Gulf Coast Condo w/Private Beach & Bay view

Gulf Views | Walkable | Spacious

Siesta Key For Me @ The Palm Bay Club

KING Bed + Anna Maria Island Beaches + Beach Gear!

Lake View 1BR Condo | Heated Pool Near Siesta

Siesta Key Beach (OHAB) Townhouse #1 beach

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Siesta Key condo, beach access, heated pool
Other waterfront vacation rentals

2BR Penthouse - Stunning Beach Views on Siesta Key

Penthouse Expansive Ocean Views

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!

Waterfront Retreat | Heated Pool & Boat Dock

Shore Side Suites

"Little Siesta" - Farm home near Terra Nova

Mid-Century Modern, Pool, Mins to Siesta Key Beach

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
Quick stats about waterfront rentals near Siesta Beach

Total vacation rentals
Explore 480 vacation rentals in Siesta Beach

Nightly prices starting at
Siesta Beach vacation rentals start at G$25,091 GYD per night before taxes and fees

Verified guest reviews
Over 13,170 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
440 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wi-Fi availability
480 of Siesta Beach vacation rentals include wi-fi access

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

4.8 Average rating
Siesta Beach stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Waterfront rentals Sarasota County
- Waterfront rentals Florida
- Waterfront rentals United States
- Anna Maria Island
- Raymond James Stadium
- Crescent Beach
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Coquina Beach
- Turtle Beach
- Lido Key Beach
- Amalie Arena
- Vinoy Park
- Caspersen Beach
- Tampa Convention Center
- Cortez Beach
- St Pete Beach
- Anna Maria Public Beach
- Manasota Key Beach
- Jannus Live
- Englewood Beach
- River Strand Golf and Country Club
- Tropicana Field
- North Beach At Fort DeSoto Park
- The Don CeSar
- Splash Harbour Water Park





