Holiday rentals with a pool in Siesta Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Siesta Key

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Condo in Siesta Key

4.95 out of 5 average rating, 122 reviews

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

Superhost

Cottage in Siesta Key

4.87 out of 5 average rating, 260 reviews

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ FREE pool, kayaks, stand up paddle boards & Tiki Hut. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private screened lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

Top Guest favourite

Guesthouse in Sarasota

5 out of 5 average rating, 206 reviews

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Guest favourite

Condo in Sarasota

4.95 out of 5 average rating, 105 reviews

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!

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 359 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

- Located in a quiet Sarasota neighborhood minutes from shopping, restaurants, & Siesta Key, this amenity packed home is perfect for families and beach enthusiasts! - Enjoy the heated pool and comfy outdoor furniture in your fenced in backyard where you can bask in the sun swimming and grilling. - Beautifully designed coastal interior w/ new appliances, Smart TVs, and fast WiFi. - Your on-site Superhost is available if needed to assist with making your stay enjoyable and worry free.

Guest favourite

Condo in Sarasota

4.87 out of 5 average rating, 115 reviews

Anchor house +6 min. from Siesta Beach+heated pool

★ "Ground floor 1 bedroom 1 bathroom apartment" ★ "An incredible apartment and 6 star hospitality!" 🌴 Stylish Retreat Near Siesta Key Heated Pool! Welcome to your perfect Sarasota getaway! This 600 sq. ft. pet-friendly home offers a heated pool access, and a prime location just 6 minutes from Siesta Key Beach. Whether you're here for a beach vacation, a family trip, or a remote work retreat, this home has everything you need for a comfortable and stress-free stay.

Superhost

Apartment in Siesta Key

4.81 out of 5 average rating, 242 reviews

Cozy, Remodeled Studio Steps from Siesta Key Beach

This beautifully designed open-concept space blends modern comfort with stylish elegance. The seamless flow between the living and dining areas creates a welcoming atmosphere, perfect for relaxation or entertainment. The cozy bedroom, featuring soft colors and plush furnishings, offers a peaceful retreat. Large windows bathe the space in natural light. For added convenience, we offer a queen airbed for additional guests, ensuring everyone enjoys a comfortable stay.

Top Guest favourite

Condo in Siesta Key

4.97 out of 5 average rating, 320 reviews

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!

Guest favourite

Condo in Siesta Key

4.84 out of 5 average rating, 238 reviews

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.

Guest favourite

Condo in Siesta Key

4.94 out of 5 average rating, 109 reviews

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.

Guest favourite

Apartment in Sarasota

4.9 out of 5 average rating, 286 reviews

VILLA 3 · Pool view. Walk to beach. Daily rentals

Villa 3 is newly renovated Everything has been remolded and upgraded Featuring 1 bedroom, 1 bathroom,With 2 person shower with beach pebble floor Separate living room, With Large SMART TV A/C, stainless steel fridge, freezer, toaster, free wifi 2 minutes walk from your door to the beach access #13 Shared swimming pool at your door Perfect for couples No smoking No pets Great Location Good Value

Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 327 reviews

NEW 3/NTS JULY OPEN! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!