Holiday rentals with a pool in Siesta Key

5 minutes to private Siesta Key Beach + 2 pools

Escape to this luxurious 1st-floor condo on Siesta Key, just 5 minutes from the award-winning Siesta Key Beach. Enjoy private access to its soft, white sand and turquoise waters. Perfect for families, the condo offers two heated pools, lighted tennis and pickleball courts, a fishing pier, gym, and sauna for endless fun and relaxation. Nestled in a tropical setting, it’s the ideal spot for your beach vacation, staycation, or a peaceful getaway. Everything you need for an unforgettable experience!

"Safe & Clean" - Key West Suite - Siesta Key Beach

Cozy 2 bedr & den apartment -beautifully updated- 2 full baths (1 King + 2 Twins + 1 Queen bed in the den, see photo's ), sleeps 6 people comfortably in beds, 1,200 sq/ft on first floor with two private balconies and partial Gulf views from the den. This apartment offers central AC, washer & dryer, dishwasher, microwave, and 2 flat screen TV's. "Gumbo Limbo Rentals" is a mini resort with only 2 duplexes that share a black bottom lagoon style pool which is heated during colder winter months.

Amazing beach view! Entire unit renovated!

The entire unit is completely renovated! Brand new furniture, appliances, and 2 55-inch smart TVs, etc. It comfortably sleeps 4 people. This 1 bedroom/1 bath unit include a California king bedroom set in the bedroom, queen and full sleeper sofas in the living room, and pack-n-play for infants. Big lanai area, enjoy amazing views of the ocean. This 3rd-floor unit steps away from #1 Siesta Key beach. This unit is a short distance to siesta key village for restaurants, shops, & entertainment.

Seaside Sanctuary

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 bar, or try your luck fishing on the pier, all while viewing the boats on the intercoastal! Included is private deeded beach access that is just a 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. 65" tv free wifi Netflix Disney+. Boat slip available up to 24'

Coastal Elegance Pool Home in Sarasota

Welcome to coastal elegance in Sarasota! - Stunning 4-bed, 4-bath pool home on Palm Island - Recently renovated with modern, open-concept layout - Gourmet kitchen featuring Italian Fulgor cooktop - Ground-floor master suite for privacy and luxury - Sun-filled flex room for various uses - Spacious outdoor area with newly renovated pool - Private dock access for boating enthusiasts - Just 2 blocks from Siesta Key Beach and 10.5 blocks from Siesta Village

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

FULLY RESTORED POST HURRICANE! HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time and post hurricane updates! If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

Palm Bay Club! Resort Style Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

Let's go to the beach and play!

Beautiful 3 bedroom house on Siesta Key, less than a mile away from the famous Siesta Key beach and Siesta Key village. Private back yard with a solar heated pool that backs up to a park, lots of privacy. Just finished renovations. Large patio with an outdoor table to enjoy a meal with your family and friends. Large driveway and 2 car garage. The park behind the house has many entertainment options for kids.

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.