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

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! Please message me if bringing 2+ pets

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!

100 Steps to the Sand!
This charming two-bed, two-bath condo offers the perfect getaway close to Crescent Beach, shops, and restaurants. Some Highlights: Comfortable seating with plush sofas and a flat-screen TV. A dining area with seating for six. A fully-equipped kitchen with stainless appliances. First bedroom offers a king size bed, walk in closet and a 4 piece bath. The second bedroom offers two queen beds, a walk in closet and a shared bathroom with the living space. Heated pool, chaise lounges provided, wifi!

Comfy Siesta Key Condo
Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

Sun-Kissed Memories!
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...!

Your Modern Beachside Getaway!
Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!

6 Siesta Breakers - Condo, Ocean View, Heated Pool
Luxurious apartment style condo on Siesta Key Beach, Sarasota Florida overlooking the quartz white sand and turquoise waters of the #1 beach in the USA. Enjoy exquisite ocean views from the balcony or just a few steps to the beach. Our gated community positions you steps away from whatever your heart desires (pool, ocean, grocery store, restaurants, live music and local shops). Your options are limitless on Siesta Key. If you need more than one condo check - airbnb.com /h/breakers203

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, kayaks & a private dock on Heron Lagoon. The Dolphin Bungalow's one bedroom space; connects a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. Fully stocked with linens, care essentials, eating & cooking utensils. A queen sofa bed in the living room, allows for a capacity of three.

Your private retreat near Siesta Key Beach.
Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

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 Getaway with King Bed
Great vacation location on beautiful Siesta Key, fully updated unit, (no busy street to cross) with private & gated direct beach access. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorgeous white sandy beaches, or swim in the crystal clear waters of the Gulf of Mexico. Come join us for the perfect vacation.

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.
Popular amenities for rentals with a pool near Siesta Beach
House rentals with a pool

Retreat by the Bay-Heated Saltwater Pool

Private Pool +Game Room Near Siesta Key | Sleeps 9

Caribbean Dream | Luxury Condo on SK w Heated Pool

Beautifully Remodeled Home with Pool Near Siesta

Luxury Canal-Front Home + Heated Pool Near Beach

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

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

Siesta Key, FL - Casa Berano
Condo rentals with a pool

Private Beach & Intracoastal Waterfront

#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Sarasota Surf & Racquet Club Siesta Key Condo

Siesta Key Condo: Beach, Pool & Village Fun!

Sarasota Surf & Racquet Club Siesta Key Condo

Seaside on Siesta Key Beach

Siesta Key Beach Front Condo
Other holiday rentals with a pool

"The Nest" Luxury 3BR, Heated Pool, Near SK Beach!

Water's Edge: Charming Canal Oasis

2BR Siesta Key Villa w/Lanai - Near Pool

The Palms Away

Heated pool & Infrared Sauna, 2 min to beach

North Water View - Residence 310

Modern, Walkable, Updated, Private.

NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach
Quick stats about rentals with a pool near Siesta Beach

Total holiday rentals
Explore 1,590 holiday rentals in Siesta Beach

Nightly prices starting at
Siesta Beach holiday rentals start at $102 AUD per night before taxes and fees

Verified guest reviews
Over 26,740 verified reviews to help you choose

Family-friendly holiday rentals
1,290 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 150 rentals that welcome pets

Rentals with dedicated workspaces
710 properties have a dedicated workspace

Wi-Fi availability
1,580 of Siesta Beach holiday 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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- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
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