
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.

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

Super Clean Cozy and Quaint steps from the beach
The best of all worlds, cleanliness and steps from the beach. Avoid the crowds at the public beach in this beautiful private beach with lounge chairs already at the beach for your convenience. Literally yards from the beach, exit the ground floor condo and walk 100 yards to the gate to the private beach. Only 2 miles from the village, with an easy close by trolley stop just outside the complex. Beach cart, umbrella, cooler, beach toys and towels provided for your convenience! Look no further.

The Palm Bay Club on Siesta key Beach
Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

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

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.

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.

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!

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.

Sea Shell Ocean View On Beach Walk Everywhere Pool
Enjoy ocean views in this 2 bed 2 bath spacious beach side 4th floor condo at Sea Shell Updated coastal decor across from Capt Curts, restaurants, grocery, coffee, ice cream Easy to WALK everywhere No car needed Perfect location Great for families Sleeps 6- 1 king & 2 queens & walk in closets Balcony with GULF views Private beach steps away from bldg. Free beach loungers. POOL Siesta Beach #1 in US Quick Wifi Superhost- 325+ reviews that ave FIVE STAR!

Siesta Key Luxury | 3BR | BEACH, Gulf Views & Pool
Luxury Beachside Retreat ✨🌊 Just steps from Siesta Key’s Public Beach, this 1,850 sqft 3BR/2.5BA townhouse offers 2 king bedrooms and a romantic loft with queen bed, private balcony + stunning Gulf views. Max. 6 guests. All 3 balconies overlook the beach. Enjoy a heated lagoon pool (shared by only 2 duplexes), free Wi-Fi, beach chairs, umbrellas & parking for 2–3 cars. The best location for your Siesta Key escape!
Popular amenities for rentals with a pool near Siesta Beach
House rentals with a pool

The Sand Castle - Backyard Oasis Mins from Siesta!

Beachfront Getaway in Siesta Key

Your private retreat near Siesta Key Beach.

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

New remodel- 150 Yds to Beach and Restaurants!

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

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

Oasis by Siesta Key Beach and Downtown SRQ w/pool
Apartment rentals with a pool

Villa Maria: Minutes to Siesta Key!

Comfy Siesta Key Condo

Siesta Key Ground Floor Condo 2BR On Trolley Line

Seaside on Siesta Key Beach

Siesta Key Beach Front Condo

Oceanfront LBK: Relax & Recharge!

5209B Menorca Street - Siesta Key Village Condo

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

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Sun-filled cottage with pool, walk to beach

Cozy Lido Key Studio-Steps to Beach & Kayaking

Charming Poolhouse · 1BR · Close to Siesta

Amazing beach view! Entire unit renovated!

Breathtaking Beachfront Views in Siesta Key

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

Tiki Bar Paradise! Heated Pool & Gaming Oasis!
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 $89 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
- Rentals with lake access Siesta Beach
- Rentals with outdoor seating Siesta Beach
- Luxury rentals Siesta Beach
- Rentals with a firepit Siesta Beach
- Rentals with a patio Siesta Beach
- Beachfront rentals Siesta Beach
- Townhouse rentals Siesta Beach
- House rentals Siesta Beach
- Rentals with a fireplace Siesta Beach
- Cottage rentals Siesta Beach
- Rentals with breakfast Siesta Beach
- Pet-friendly rentals Siesta Beach
- Rentals with a washing machine and dryer Siesta Beach
- Flat rentals Siesta Beach
- Rentals with beach access Siesta Beach
- Apartment rentals Siesta Beach
- Rentals with an EV charger Siesta Beach
- Villa rentals Siesta Beach
- Rentals with a kayak Siesta Beach
- Fitness-friendly rentals Siesta Beach
- Rentals with a hot tub Siesta Beach
- Beach house rentals Siesta Beach
- Waterfront rentals Siesta Beach
- Family-friendly rentals 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
- Caspersen Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- Manasota Key Beach
- River Strand Golf and Country Club
- Englewood Beach
- Gulfport Beach Recreation Area
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- Myakka River State Park
- The Don CeSar
- Lakewood National Golf Club
- Stump Pass Beach State Park




