
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.

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

Crystal House on Siesta Key Beach
This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

Oceanfront LBK: Relax & Recharge!
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!

Sarasota Surf & Racquet Club Siesta Key Condo
Sarasota Surf and Racquet Club is located on Siesta Key's award winning Crescent Beach. Our condo unit has all of the amenities of home for your convenience. The master bedroom has a king sized bed and it's own ensuite with walk-in shower. The second bedroom has 2 beds with a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

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.

Adorable Cozy Silver Sands Cottage on Siesta Key!!
Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, Keurig in the kitchen, stocked with everything but your clothes and toothbrush.

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.

Steps to Siesta Beach | Chic Studio / Pool & Patio
Bright & Stylish Retreat ✨ This beautifully designed open-concept home blends modern comfort with elegant style. Relax in the airy living/dining space, unwind in the serene bedroom, and soak up natural light from large windows. Enjoy your private patio, take a dip in the pool, and use the queen airbed for extra guests—perfect for couples, friends, or family. Max 4 guests.

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

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

5 minutes to private Siesta Key Beach + 2 pools

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

Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

Beach Retreat•Renovated Pool Patio•Near Siesta Key

Private Siesta Beach House Oasis with Heated Pool.

Newly Reno Cozy 1BR w/ Pool - Walk to Gated Beach
Apartment rentals with a pool

Steps away from beach and village! #1 in Siesta!

Villa Maria: Minutes to Siesta Key!

Siesta Key For Me @ The Palm Bay Club

Best Deals on Siesta Key

Comfy Siesta Key Condo

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Siesta Key Beach Front Condo

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

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

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Private Beach Access - Spacious & Modern Gem!

Cozy Top-Floor Stay on Siesta Key

Amazing beach view! Entire unit renovated!

Breathtaking Beachfront Views in Siesta Key

Super Clean Cozy and Quaint steps from the beach

House Of Sun-Ocean Views On Beach. Walk Everywhere
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 $88 SGD 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
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- Rentals with pools Sarasota County
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- Rentals with pools United States
- Anna Maria Island
- Crescent Beach
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- John's Pass
- Turtle Beach
- Coquina Beach
- Caspersen Beach
- Vinoy Park
- 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
- Gulfport Beach Recreation Area
- Myakka River State Park
- The Don CeSar
- Lakewood National Golf Club
- Stump Pass Beach State Park




