
Waterfront holiday 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.

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.

Oceanfront: Open Su - Th, $250/night!
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 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!

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'

KING Bed + Anna Maria Island Beaches + Beach Gear!
⚓️🦩Welcome to the Coastal Flamingo! Your nautical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this coastal escape!

Kayak w/ Dolphins - Private Entrance Studio
Paddle with dolphins in Palma Sola Bay from this private-entrance, 2-room studio with living room, bedroom w/ queen, bathroom, food prep area (no kitchen sink). Two TVs, WIFI. Dock access in back yard includes use of kayaks/canoe or docking your boat. Quiet on dead-end street. Owner lives in back of house facing canal (see photo). Your space is private with a tropical street entrance & access to the back yard. Non-shedding dog considered with prior approval.

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. Enjoy 2 free bikes day rental with booking!

Palm Bay Club! Resort Style 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 Keys stylish and affordable Airbnb.
Relax while you stay in a colorful and warm Siesta Key/Sarasota neighborhood home that is only minutes from the famous Siesta Key beach. Enjoy your private, safe, and comfortable suite while being in close reach to all that Florida has to offer. Your suite is spacious and accommodating, wether your an individual, couple, family, or group of friends we have the space and amenities for you to maximize both your comfort and fun time while here in Florida :-)

Bradenton Beach Sunsets 1, Anna Maria Island, FL
Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

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.

2/2 Beach House Apt on Siesta Key
Siesta Key Waterfront Apartment. Sleeps 6. Split plan 2 bedroom, 2 full bathroom “Beach House” w/ a full kitchen & recently updated! Bedroom 1: King. Bedroom 2: Queen. Living room: Sleeper sofa. 75” smart TV in the living room. A private screened lanai overlooking canal to Sarasota Bay. This is located in a super cute, quaint resort w/ other units. FREE KAYAKS & SUPs FOR GUESTS!
Popular amenities for waterfront rentals near Siesta Beach
Waterfront apartment rentals

Newly Remodeled Beachfront Studio - On the sand!

Siesta Sunsets Suite

Sweet Retreat at Shorewalk!

Las Palmas Beach Rentals Unit 1

Longboat Key-OCEAN FRONT- on the beach

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

Serenity on the Manatee

Siesta Key Condo. Sit by the water !
Waterfront house rentals

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

Coastal Retreat near Siesta Key Beach and Downtown

Tranquility on the bay.

Spacious & Modern Gem ~ Walk to Gated Beach ~ Pool

Luxury Canal-Front Home + Heated Pool Near Beach

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

Sea Club II Garden House
Waterfront apartment rentals

Bayside Sunrise Cottage on Siesta Key!

Sea Shell Ocean View On Beach Walk Everywhere Pool

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

The Beach Condo #107 Beachfront Full View

Crystal House on Siesta Key Beach

A&A's Paradise near IMG & Anna Maria beaches

Sunset and beach view from your balcony Unit 403

Lake View 1BR Condo | Heated Pool Near Siesta
Other waterfront holiday rentals

2 BR condo in Siesta Key w/ Private beach access

Beachfront Paradise! Ground level with Heated pool

Waterfront Retreat | Heated Pool & Boat Dock

4BR Waterfront Escape • Spa + Dock Access

the Seaside 21

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

Amazing beach view! Entire unit renovated!

Breathtaking Beachfront Views in Siesta Key
Quick stats about waterfront rentals near Siesta Beach

Total holiday rentals
Explore 360 holiday rentals in Siesta Beach

Nightly prices starting at
Siesta Beach holiday rentals start at £59 per night before taxes and fees

Verified guest reviews
Over 11,930 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
330 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wifi availability
360 of Siesta Beach holiday rentals include wifi 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!
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- Waterfront rentals Sarasota County
- Waterfront rentals Florida
- Waterfront rentals United States
- Anna Maria Island
- Crescent Beach
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Vinoy Park
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Manasota Key Beach
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Englewood Beach
- Splash Harbour Water Park
- Myakka River State Park
- North Beach At Fort DeSoto Park
- The Don CeSar
- Point Of Rocks




