
Home rentals with a pool near Siesta Beach
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Top-rated rentals with a pool near Siesta Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

2 Bed/2 Bath Condo Resort View on Siesta Key Beach
Amazing 2nd floor unit in building C at the Sarasota Surf & Racquet Club. This fully furnished 2 bed/ 2 bath condo offers a resort view and just steps away from the white sands of Siesta Key Beach. This unit is recently updated with an open floor plan, featuring stainless steel appliances, granite counter tops, kitchen bar with stools, living room, and dining room. This unit has flat screen tv's, ceiling fans, and maid service including linens and bath towels. Washer/dryer located down the hall

Luxurious Private Retreat - Your Siesta Key Oasis!
Your dream vacation awaits with a renovated, spacious, and private single-level house. It's a perfect getaway for a relaxing vacation! Enjoy all the comforts of home while being just a short walk away from restaurants, bars, and Siesta Key's beautiful white sand beaches. Nestled on a quiet tree-lined street and tropical gardens, this retreat offers tranquility and serenity. The community boasts a large heated pool and intercoastal waterway pier, ideal for afternoon fishing or sunset beverages!

Your private retreat near Siesta Key Beach.
Welcome to your private Retreat! Nestled at the end of a quiet dead-end street. This distinguished property guarantees a relaxing Florida vacation for everyone! Completely remodeled with Coastal-Modern Decor. 3 bedroom, 2 bath, amazing heated pool home and private back yard is located in the Gulf Gate Estate neighborhood. A short drive (less than 2 miles) to the white coastal sands of Siesta Key Beach, Gulf Gate shopping mall, grocery store, restaurants, cafes. Must be at least 25 years old

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed and private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional queen sofa-bed allows accommodations for three guests.

Toes In The Sand | Private Pool, Walk to Beach!
🦩Exclusive Amenities Include: • Private Heated Pool • 3 Minute Walk to Siesta Key Village • 1 Minute Walk to Siesta Key Beach • Outdoor Lounge Area • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Caddy • Gas Grill • Enhanced cleaning protocols by our CottageClean Team • Island Shuttle Transportation Available • Dog Friendly (1 dog up to 25 lbs with an additional fee)

The Palms Away
This special place is close to everything, making it easy to plan your visit. 1 mile to Siesta Key. Built in the 50's but totally renovated to today standard's. Heated swimming pool, but if the water gets to hot the heater will also cool the pool. Very close to shopping. Large deck with view to tropical garden and waterfall. Gas fire pit with built in seating. Small putting green and Corn-hole game are available for your use. 5 TV's with wi-fi. A Gazebo with plenty of sitting area.

Seaside on Siesta Key Beach
Seaside on Siesta is the perfect walkable location to everything you need for a seaside getaway! Located directly across the street Siesta Key Beach. NEWLY RENOVATED in 2025. Walk or take the FREE trolley (trolley stop located feet from our front patio) to Siesta Key Village. First floor unit so no need to wait on elevators. The spectacular white quartz beach and crystal clear water awaits you just outside your door! Search "Seaside on Siesta Tour" on Youtube for a video tour.

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.

The Sand Castle - Backyard Oasis Mins from Siesta!
*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want!

Cozy 1BR Beach Condo on Siesta Key!
Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.

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 rentals with a pool near Siesta Beach
House rentals with a pool

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

New remodel- 150 Yds to Beach and Restaurants!

Pool house with outdoor shower, 10 minutes from SK

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Oasis by Siesta Key Beach and Downtown SRQ w/pool

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Sarasota Escape | Minutes to Beaches + Downtown

Sarasota Waterfront Pool Home with Dock
Condo rentals with a pool

Steps away from beach and village! #1 in Siesta!

Beautiful White Sand Siesta Key Beach

Siesta Key Serenity At The Palm Bay Club

Comfy Siesta Key Condo

Sunset and beach view from your balcony Unit 403

6 min to Siesta Beach | Heated Pool | Lake View

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Oceanfront LBK: Open Sun & Mon, $185/nt + Fees!
Other holiday rentals with a pool

615 Luxury Condo With Ocean View, Heated Pool +++

Beachfront Getaway in Siesta Key

Beechwood Suites A

Amazing beach view! Entire unit renovated!

Breathtaking Beachfront Views in Siesta Key

Beach & Pool Open! Direct Beachfront Condo! Sunset

New Villa on Siesta Key! Pool & Walkable to Beach

Sleep 6, walk to beach, restaurants/bars, new reno
Quick stats about rentals with a pool near Siesta Beach

Total holiday rentals
Explore 1,510 holiday rentals in Siesta Beach

Nightly prices starting at
Siesta Beach holiday rentals start at $107 NZD per night before taxes and fees

Verified guest reviews
Over 25,860 verified reviews to help you choose

Family-friendly holiday rentals
1,220 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
690 properties have a dedicated workspace

Wi-Fi availability
1,500 of Siesta Beach holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- Rentals with pools Sarasota County
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- Anna Maria Island
- Crescent Beach
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Splash Harbour Water Park
- Manasota Key Beach
- Englewood Beach
- North Beach At Fort DeSoto Park
- Point Of Rocks
- Don CeSar Hotel
- Lakewood National Golf Club




