
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 Honeymoon Suite on Siesta Key Beach
This is a recently renovated honeymoon suite located directly across from the big end of Siesta Key. It is an elegant ground floor pool unit. This unit is equip with marble countertops, tigers eye, lapis lazuli tables, bladeless ceiling fan, alabaster lighting and giant TVs. All of the appliances are stainless/smart and the microwave can cook steaks. There is a gym. The geographic location on the key can not be beat! There is a floating television over the California King luxury memory foam bed.

Luxury 3B/3B waterfront home w/ pool + boat access
Escape to this luxurious 3BR/3BA Sarasota sanctuary! 5 minutes from Siesta Key, this Mid-Century Modern gem sits on a canal with direct Bay access (no bridges). Dive into the private pool & spa, lounge on the 1,000 sq ft porch, or relax inside on cozy furnishings. Includes a private dock, kayak/SUP/canoe, bikes, and a massive driveway for boat trailers. From the hanging bed swing to the gourmet kitchen, every detail is designed for your dream waterfront getaway. Your Florida paradise awaits!

Siesta Key, FL - Casa Berano
Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beaches 7 days/wk. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets max (dogs only), under 50lbs.

Bike to Beach Double King Suites, Pool & Mini Golf
Escape to the Salt & Sol House- a luxe coastal boho getaway just minutes from the white sands of world class Siesta Key Beach. This newly designed vacation rental offers everything for your perfect Florida escape. Enjoy indoor outdoor living, a heated pool, private putting green, bikes for exploring, hammocks in the shade, and twinkling string lights that create unforgettable evenings. Experience pure relaxation with resort-style amenities and luxury in paradise. BONUS: We are pet-friendly!

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.

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.

Private Heated Pool Retreat for Two Families
🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.

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

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.

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!

Siesta Key | Heated Pool | Sauna | Family & Pets
☞ Sauna, Fire-pit, BBQ (gas) ☞ Giant Outdoor Chess♟️ ☞ King & 2 Queen Beds ☞ Ample Parking (RV, Boat, etc) ☞ Fast WiFi 🛜 ☞ 4 Smart TVs (largest 85 inches) ☞ Gourmet Kitchen Main side ☞ Kitchenette on Guest side ☞ 2 Onsite washer + dryers ☞ 2 Outdoor Showers 》30 mins to airport 》2 mins to Siesta Key Beach Bike to America’s #1 beach, morning coffee runs, sunset rides, live music, ice cream, shops or any of the amazing restaurants in Siesta Key village.
Popular amenities for rentals with a pool near Siesta Beach
House rentals with a pool

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

Chic Siesta Retreat – Pool, Hot Tub & Water Views

The Palms Away

Beautifully Remodeled Home with Pool Near Siesta

Beach, Village, Dock & Private Pool! One-of-a-kind

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Heated saltwater pool near Siesta and Downtown

Mid-Century Modern, Pool, Mins to Siesta Key Beach
Apartment rentals with a pool

Beautiful White Sand Siesta Key Beach

Beach Retreat - Jamaica Royale Unit #52

Sarasota Surf & Racquet Club Siesta Key Condo

[Beach Elements] pool view + private beach & bikes

Seaside on Siesta Key Beach

Siesta Key Beach Front Condo

Island Time: Open Tomorrow, $150/nt + Fees!

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool
Other holiday rentals with a pool

Private Pool +Game Room Near Siesta Key | Sleeps 9

Siesta Serenity ~ Pool/Waterslide/Waterfront

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

Heated pool & Infrared Sauna, 2 min to beach

True Island Living House/beach/water views

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

Modern, Walkable, Updated, Private.

Seabreeze Pool Retreat.
Quick stats about rentals with a pool near Siesta Beach

Total holiday rentals
Explore 1,680 holiday rentals in Siesta Beach

Nightly prices starting at
Siesta Beach holiday rentals start at $76 SGD per night before taxes and fees

Verified guest reviews
Over 27,920 verified reviews to help you choose

Family-friendly holiday rentals
1,430 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 150 rentals that welcome pets

Rentals with dedicated workspaces
740 properties have a dedicated workspace

Wifi availability
1,670 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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- Rentals with pools Sarasota County
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- Anna Maria Island
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- Turtle Beach
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- Vinoy Park
- Amalie Arena
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- North Beach At Fort DeSoto Park
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