
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.

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.

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

Beach Retreat - Jamaica Royale Unit #52
Casually elegant condo fully remodeled in 2025, and very close to beach! One bedroom, one bath unit includes quartz kitchen counters, new appliances, king bed and relaxing patio. Perfect size for 2 guests! No need to cross busy roads to get to stunning white sand; just a 5 -10 minute walk along lush grounds which boast 3 heated pools. Beach gear provided, and unit is stocked with linens and kitchen utensils. Minutes away from Siesta Village and other wonderful dining and activities.

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.

Beautifully Remodeled Home with Pool Near Siesta
It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

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.

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.

[Beach Elements] pool view + private beach & bikes
Relax & Recharge at Siesta Beach in a poolside one-story villa. +2 beach cruiser bikes ( $40 each per stay) NEWLY REMODELED!! King size bed + queen sofa bed This modern studio is fully equipped with a kitchen, granite countertops & stainless steel appliances. King size bed and full-size sleeper sofa. Recently updated kitchen, bathroom, and a complete living area. It overlooks 1 of 3 pools Enjoy the morning sun, with your coffee on the patio.
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!

The Sand Castle - Backyard Oasis Mins from Siesta!

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

The Palms Away

Luxury Canal-Front Home + Heated Pool Near Beach

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

True Island Living House/beach/water views

Bike to Beach Double King Suites, Pool & Mini Golf
Condo rentals with a pool

Beautiful White Sand Siesta Key Beach

Gulf Views | Walkable | Spacious

Sarasota Surf & Racquet Club Siesta Key Condo

Seaside on Siesta Key Beach

Siesta Key Beach Front Condo

Island Time on LBK!

Private Siesta Key Escape

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

2BR Penthouse - Stunning Beach Views on Siesta Key

Private Pool +Game Room Near Siesta Key | Sleeps 9

Direct Gulf View - Residence 603

Walk to Siesta Village, Heated Saltwater Pool

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

Private Heated Pool Retreat for Two Families

Modern, Walkable, Updated, Private.

Outdoor Coastal Living: Pool, Hot Tub, Patio, Dock
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 $83 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 150 rentals that welcome pets

Rentals with dedicated workspaces
740 properties have a dedicated workspace

Wifi availability
1,670 of Siesta Beach vacation 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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