
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.

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!

Luxury King Suite
Start your day with a refreshing cup of coffee, then stroll to the white sands of Siesta Key beach. Allow the sun and the ocean to bring you home to nature. The cool, white sand refined from 99% quartz powder is unlike anything else in the World. Watch the sunset over the soft rolling waves of ocean water, then come back to your luxury condo and refresh for an evening on the key. Immaculately clean, perfect location, and a true beach oasis—book now for the ultimate Siesta Key experience!

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

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.

Oceans2
This condo is set in the perfect location between the beach and the bay! Soak up the sun at the heated pool, enjoy the tiki hut, or try your luck on the fishing pier, all while viewing the boats on the intercoastal as they pass by. Included is a private deeded beach access that is an easy 5 min walk . Hop on the free trolley right outside your door to go to Siesta Key Village with plenty of restaurants, bars and shops only .5 miles away. Boat slip available for up to 24' .

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.

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!

Lovebirds’ Retreat | Steps to Siesta Key Beach
Romantic Honeymoon Suite 💕 Steps from Siesta Key Beach, this 1BR/2BA townhouse is perfect for two. Enjoy 2 balconies with sunset views of the beach, pool & gardens, central AC, and a heated lagoon-style pool for dreamy evening swims. Max 4 guests. Complimentary Wi-Fi, beach chairs & parking for 1 car make this the ultimate couples’ escape.

Siesta Key Condo. Checkout our great rates!
Our beautiful Siesta Key condo is located a short stroll from the famous Siesta Key beach with its beautiful quartz sand and amazing sunsets. The Midnight Cove II condominium complex has private beach access with outstanding amenities and is very family friendly, come and enjoy the natural beauty this complex and all Siesta Key has to offer.
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.

New remodel- 150 Yds to Beach and Restaurants!

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

Beach Retreat•Renovated Pool Patio•Near Siesta Key

Spectacular Sunsets! 15 min Siesta Key!
Condo rentals with a pool

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

Sea Shell Ocean View On Beach Walk Everywhere Pool

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

Villa Maria: Minutes to Siesta Key!

Sunset and beach view from your balcony Unit 403

Siesta Key Ground Floor Condo 2BR On Trolley Line

Seaside on Siesta Key Beach

Siesta Key Beach Front Condo
Other holiday rentals with a pool

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Siesta Key Village, Pool, Beach Access 4-min Walk

Siesta Sunsets Suite

Cozy Lido Key Studio-Steps to Beach & Kayaking

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

Amazing beach view! Entire unit renovated!

Breathtaking Beachfront Views in Siesta Key

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 $99 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 150 rentals that welcome pets

Rentals with dedicated workspaces
710 properties have a dedicated workspace

Wi-Fi availability
1,580 of Siesta Beach holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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