Siesta Key Vacation Rentals
Discover the best Siesta Key vacation condos & homes for your coastal escape
Our collection of Siesta Key vacation rentals features homes and condos of all sizes, with amenities including beachfront locations, beach views, pet-friendly options, private pools, and more! Whether you're visiting for a couple's retreat or a family getaway, our properties provide the perfect space to call home on your beach adventures. Several of our condos are located in Siesta Key's top resort communities, such as Tivoli by the Sea, Bianco Sands, and Gulf and Bay Club. Choose from 1- to 7- bedroom accommodations and be within walking distance to some of Siesta Key's top attractions like Siesta Key Village, Siesta Beach, Crescent Beach, and so much more!
Browse our Siesta Key vacation rentals below, or contact us and let us help you plan your beach vacation!
98 properties available
Step into tranquility at this charming private home, nestled in the heart of Siesta Key. Just a short walk from the famous powder-soft sands of Siesta Beach, this home offers the perfect blend of convenience and relaxation. Featuring a private kitchen, living room, and an onsite private pool, this cottage is perfect for winding down after a day in
Step into tranquility at this charming 1-bedroom cottage, nestled in the heart of Siesta Key. Just a short walk from the famous powder-soft sands of Siesta Beach, this home offers the perfect blend of convenience and relaxation. Complete with a private kitchen, living room, and an onsite shared pool and hot tub, this cottage is perfect for winding
Step into tranquility at this charming 1-bedroom cottage, nestled in the heart of Siesta Key. Just a short walk from the famous powder-soft sands of Siesta Beach, this home offers the perfect blend of convenience and relaxation. Featuring a king size bed, private kitchen, living room, and an onsite shared pool and hot tub, this cottage is perfect f
Welcome to Las Palmas! This gorgeous new home on Siesta Key offers luxury around every turn. Stay with up to 16 guests in this 7-bedroom, 7.5-bathroom home, complete with a private pool and spa area, fenced in yard, large full kitchen, dining room, two living spaces with a game room, and much more! Spend time outside by the pool, featuring a kid’s
Welcome to the enchanting Crystal Sands - Sea La Vie, your perfect beach side retreat in the heart of Siesta Key. This charming two-bedroom villa offers a cozy and inviting space for up to 5 guests and features a full kitchen and spacious living room accompanied by a cozy nook. Guests enjoy access to two heated pools, and a private beach area. Expe
This must-see home on Siesta Key offers a much sought after modern and contemporary design. With plenty of space for the entire family. This unit, located on the 2nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 10 guests. Complete with a full kitchen, living, and dining space, make this place your home away from home and
This must-see home on Siesta Key offers a much sought after modern and contemporary design. With plenty of space for the entire family. This unit, located on the 1nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 10 guests. Complete with a full kitchen, living, and dining space, make this place your home away from home and
Spend your vacation relaxing in this lovely 3-bedroom, 2.5-bathroom townhome. On the ground level, you will find covered parking for up to 2 cars, and storage. The second level hosts an open concept for the living room, dining, and kitchen areas. The spacious living room features rattan ceiling panels for a casual coastal vibe. The kitchen offers p
Spend your vacation relaxing in this lovely 3-bedroom, 2-bathroom townhome. On the ground level, you will find parking for up to 2 cars. The second level hosts a spacious living room, dining, and kitchen areas. The kitchen offers plenty of storage and stainless countertops. The living room offers space for the entire family to relax with large wind
Peace and Relaxation! Enjoy your vacation in a spacious 5 bedroom 3.5 bathroom home on Siesta Key with a private pool and a fenced in yard. This home features 3 livings rooms, a full kitchen, and plenty of space for the whole family. Perfectly located for a trip to the beach or a short walking into the Siesta Key Village, this lovely vacation home
Beach that offers the whitest and softest sand in the World that is always cool to the touch. Relaxing and making your memories is all that’s required but located just minutes is down town’s rich art and cultural community. In the village of Siesta, you’ll be welcomed to enjoy a cool beverage under the palm trees while listening to live music, take
This luxury 2 Bed, 2.5 Bath townhouse comfortably sleeping up to 4 guests! Complete with a beautiful kitchen, and dining area, a large laundry room, and plenty of space to relax by the pool on your island vacation! Just one block from our world-famous, beautiful Siesta Beach, this home is in the best location for a relaxing get-away. Enjoy beautifu
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