
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.

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.

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.

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.

Luxury 4B Home & Heated Pool, Resort for 10 guests
Minutes to Siesta Key Beach, this Sarasota home is made for effortless group getaways. Start your mornings by the private screened pool, unwind on the cabana daybed, and gather in bright open living spaces designed for connection. Enjoy a fully equipped kitchen, 3 full bathrooms, and a separate studio offering extra space and privacy. Centrally located with quick access to St. Armands Circle, The Ringling, and Mote Marine Laboratory & Aquarium—perfect for dining, culture, and family fun 🌴

Island Time on LBK!
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!

Modern, Bright Downtown SRQ A-Frame West of Trail
Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

Pool, Shuffleboard, EV charg, Near beach, UTC mall
Welcome to Vistalodgings Villa Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

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.

Charming Poolhouse · 1BR · Close to Siesta
Modern, peaceful apartment in a three-unit property, featuring a shared, year-round heated pool and fenced backyard, used exclusively by the three guest units. Siesta Key Beach is about a 4-minute drive, while the setting remains quiet and relaxing. • Pet-friendly – flat $10 pet fee per reservation, regardless of number of pets • shared heated pool (only for the 3 on-site units) • shared fenced backyard • large shared gas BBQ grill

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

Sarasota's Luxury Oasis

Luxury 3B/3B waterfront home w/ pool + boat access

The Palms Away

Luxury Lido Key Getaway on St. Armands Circle

Siesta Serenity ~ Pool/Waterslide/Waterfront

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

Bike to Beach Double King Suites, Pool & Mini Golf

Private Heated Pool Retreat for Two Families
Condo rentals with a pool

6 Siesta Breakers - Condo, Ocean View, Heated Pool

Gulf Views | Walkable | Spacious

Beach Retreat - Jamaica Royale Unit #52

Siesta Key For Me @ The Palm Bay Club

Sarasota Surf & Racquet Club Siesta Key Condo

Siesta Key Ground Floor Condo 2BR On Trolley Line

[Beach Elements] pool view + private beach & bikes

Heated Pool Apartment Near Siesta Key | 1BR
Other vacation rentals with a pool

Stunning New 3 bed 3 bath pool home by Siesta Key!

Serenity Springs | Private Heated Pool + Waterfall

New listing - Pool Home, 500ft to Beach!

True Island Living House/beach/water views

Is this Heaven? No, it's Longboat Key

Siesta Key House, Pool & Hot Tub, 1 mile to beach

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

Siesta Key*PRIVATE BEACH*Gulf Side*Heated Pool
Quick stats about rentals with a pool near Siesta Beach

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

Nightly prices starting at
Siesta Beach vacation rentals start at R 994 ZAR per night before taxes and fees

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

Family-friendly vacation rentals
1,430 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 150 rentals that welcome pets

Rentals with dedicated workspaces
740 properties have a dedicated workspace

Wi-Fi availability
1,670 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!
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- Rentals with pools Sarasota County
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- Anna Maria Island
- Raymond James Stadium
- Crescent Beach
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Coquina Beach
- Lido Key Beach
- Turtle Beach
- Amalie Arena
- Vinoy Park
- Caspersen Beach
- Tampa Convention Center
- Cortez Beach
- Manasota Key Beach
- Tropicana Field
- St Pete Beach
- Anna Maria Public Beach
- Englewood Beach
- Jannus Live
- River Strand Golf and Country Club
- North Beach At Fort DeSoto Park
- Myakka River State Park
- The Don CeSar





