
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 - Private Beach Access - 2BR Retreat
Stay, relax, and play-your Siesta Key retreat is here. Make lasting memories at this cozy Siesta Key townhouse, just steps from the famous white sands. Private beach access and no roads to cross, it’s safe and stress-free for the whole family. Relax in spacious living areas, cook in the full kitchen, or enjoy games and movie nights after a day in the sun. Highlights include 2 bedrooms, private parking, nearby shops and dining, and the free Siesta Key Breeze Trolley for easy island exploring.

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!

The Flamingo's Nest at Sea Club II
The Flamingo's Nest at Sea Club II features a beautiful new pool on the intracoastal waterway, a tiki hut for on-site cocktail hours, a plethora of boats and sea birds to enjoy while cooking on our new charcoal grills, a fishing pier, boat basin, and private beach access directly across the street. We are located 1.5 miles from the Village, loaded with amazing shops, restaurants, and night life. Condo remodeled top to bottom in 2019. Beach towels, chairs, and accessories provided.

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.

Seaside on Siesta Key Beach
Seaside on Siesta is the perfect walkable location to everything you need for a seaside getaway! Located directly across the street Siesta Key Beach. NEWLY RENOVATED in 2025. Walk or take the FREE trolley (trolley stop located feet from our front patio) to Siesta Key Village. First floor unit so no need to wait on elevators. The spectacular white quartz beach and crystal clear water awaits you just outside your door! Search "Seaside on Siesta Tour" on Youtube for a video tour.

Beachfront Resort, Ocean View, Pool, Tennis, Gym
Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

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.

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.

Beautiful White Sand Siesta Key Beach
This studio has lots of space and is across from the pool and just a few short steps from the beautiful Siesta beach. Known for it powder sand white beach and tropical breeze. Average Temperature is 70. The two large pools are heated all year. This unit has one king mattress . There are shuffleboard courts an tennis court and is close to everything.

Beachfront Getaway in Siesta Key
Beachfront complex, this gorgeous home boasts all the luxury you’d expect from a beach house! Beachfront BBQ grills, cabana with lounge chairs,heated swimming pool, Wi-Fi & parking. For your convenience, there are restaurants, grocery store, pharmacy, 24 hours 7-Eleven, bike and Kayak rentals just across the street. A little piece of paradise!
Popular amenities for rentals with a pool near Siesta Beach
House rentals with a pool

The Sand Castle - Backyard Oasis Mins from Siesta!

Your private retreat near Siesta Key Beach.

Location! Siesta 1 mile away. Home with HOT SPA.

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

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Beach Retreat•Renovated Pool Patio•Near Siesta Key

Sea Club II Garden House

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough
Apartment rentals with a pool

Bayside Sunrise Cottage on Siesta Key!

Sea Shell Ocean View On Beach Walk Everywhere Pool

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

Sarasota Surf & Racquet Club Siesta Key Condo

Comfy Siesta Key Condo

Sarasota Surf & Racquet Club Siesta Key Condo

5209B Menorca Street - Siesta Key Village Condo

Near beach. Daily rentals. Pool. king bed
Other holiday rentals with a pool

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Sun and Sea Gem on Siesta Key

Private Standalone Home - Walk to Siesta Key Beach

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Lido Key FL Studio/Efficiency 5

2BR Beach Club – Beach, Heated Pool & Hot Tub

Breathtaking Beachfront Views in Siesta Key

Heated Pool, Dock, Kayaks, 1-mile to Turtle 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 £52 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 150 rentals that welcome pets

Rentals with dedicated workspaces
710 properties have a dedicated workspace

Wifi availability
1,580 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!
Destinations to explore
- Pet-friendly rentals Siesta Beach
- Beach house rentals Siesta Beach
- Fitness-friendly rentals Siesta Beach
- House rentals Siesta Beach
- Rentals with a fireplace Siesta Beach
- Rentals with a firepit Siesta Beach
- Rentals with lake access Siesta Beach
- Cottage rentals Siesta Beach
- Rentals with a patio Siesta Beach
- Waterfront rentals Siesta Beach
- Flat rentals Siesta Beach
- Rentals with beach access Siesta Beach
- Rentals with a washing machine and dryer Siesta Beach
- Rentals with a kayak Siesta Beach
- Family-friendly rentals Siesta Beach
- Rentals with outdoor seating Siesta Beach
- Luxury rentals Siesta Beach
- Apartment rentals Siesta Beach
- Rentals with an EV charger Siesta Beach
- Villa rentals Siesta Beach
- Beachfront rentals Siesta Beach
- Rentals with breakfast Siesta Beach
- Townhouse rentals Siesta Beach
- Rentals with a hot tub Siesta Beach
- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Crescent Beach
- Raymond James Stadium
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Caspersen Beach
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- Manasota Key Beach
- River Strand Golf and Country Club
- Englewood Beach
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- The Don CeSar
- Gulfport Beach Recreation Area
- Myakka River State Park
- Lakewood National Golf Club
- Tampa Convention Center




