Siesta Key Vacation Rental Homes By Owner

We invite you to stay in our spacious condo managed by The Anchorage Community Rental Program. The Community Rental Program provides quality homes at a fair price... Read More

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Nearly Beachfront Home with Gorgeous Gulf of Mexico,... Read More

This FULLY REMODELED 2-BR, 1-BA HOME accommodates up to SIX people. It is IDEALLY-LOCATED in an amazing and unique location: just steps away from The Village and... Read More

Welcome to Siesta Key!! This 2 bedroom condo offers bay views, is an end unit, has a light and bright interior, and just steps from the Bayfront pool! There is a... Read More

This FULLY REMODELED 1-BR, 1-BA COTTAGE accommodates up to THREE people. It is IDEALLY LOCATED in an amazing and unique location: just steps away from The... Read More

White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta... Read More

White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta... Read More

Recently updated with tasteful coastal decor. Our private beach, pools and bay are not crowded at all. Two heated pools, tennis courts, pickleball and sauna. The... Read More

Stay in one of the most family-friendly and safe communities on the key. We are a gated community, 5 minute walk across the street to private beach access and a... Read More

Full house, 80 steps to the Gulf and just minutes to the world-famous Siesta Key Beach and all the shops, restaurants and pubs of Siesta Key Village. Cast your... Read More

PRIVATE BEACH with full ocean views throughout the condo awaits you!!! Experience the most amazing beach views on the Gulf of Mexico from the 15th floor of the... Read More

The Siesta Key Beach Cottage is located right on Beach Rd directly across the street from the #1 Beach in the USA. Walk out the front door and walk across the... Read More

Enjoy your private beach at Crescent Arm. Beach chairs set up for you every morning and brought back to the seawall every evening for free. Saturday to Saturday... Read More

The Siesta Key Beach Cottage is located right on Beach Rd directly across the street from the #1 Beach in the USA. Walk out the front door and walk across the... Read More

Sip on ice cold drinks made at the wet bar, lounge in the private pool under the lanai, and make memorable meals at home in the fully equipped kitchen during your... Read More

“GEM” at Barefoot Bungalows is a 2 bedroom, 1 full bath, fully furnished unit on 2nd floor. This beach cottage offers the comforts of home with the location of a... Read More

Experience the beauty of Siesta Key when you and your whole beach-loving crew stay at this fabulous 2-bedroom, 1.5-bathroom vacation rental at Midnight Cove II.... Read More

Beautiful Duplex located 1 house away from beach! Amazing Location! These beautifully decorated duplexes feature all the conveniences of home with a fully... Read More

Across the street from Beach Way East is Siesta Key beach & Pavilion!! Gorgeous condo on the 3rd floor (elevator) sits right across the street from the BEST... Read More

Get ready for relaxation with your loved ones at this waterfront Siesta Key vacation rental! Featuring a lush backyard and a lanai complete with a heated pool,... Read More