Siesta Key is an incredible vacation destination during any season, but fall really is one of the best times to visit. The weather is warm but not too humid, allowing you to make the most of your time in the sun while also avoiding the crowds. It’s also a great place to spend Thanksgiving with the extended family! Here are the top Siesta Key beach vacation rentals available in the fall. 

Point Break – 336 de Mayo

Point Break is one of the best rentals on Siesta Key. Spend your evenings watching spectacular sunsets from the roof top deck with city and Gulf views. The property is only a few steps away from Siesta Key village shops, nightlife, restaurants and Siesta Key Beach. When you’re not out on the sand or exploring local shops, kick back and relax in the house’s heated resort pool with sun shelf, jacuzzi/spa, and more. Kids will entertain themselves for hours in the arcade room, which includes multiple gaming systems. This is a multi-floor house with 8 bedrooms, 8.5 bathrooms, and elevator access to all floors. Up to 24 guests can be accommodated. For an additional fee, even the family dog can join in the fun!

Sunset Splash – 95 Avenida Messina

Sunset Splash is a beautiful and spacious 8 bedroom 7.5 bathroom luxury home that can accommodate up to 23 guests, all on the ground level for easy access. The open floor plan encourages family or friends to gather and enjoy their vacation time together, just what holidays are for! It’s also located a block away from Siesta Key Beach.

Blue Paradise – 5234 Navarra

Discover your dream vacation rental at Blue Paradise. With a heated private saltwater pool, spa with rain curtain, waterfall, sun shelf, and covered pool bar, you may find it difficult to leave the house! There are 6 bedrooms and 6.5 bathrooms with a sleeping capacity of 18. To sweeten the deal, every bedroom includes an en suite bath! The house is brand new and centrally located, less than a minute’s walk from the beach and village.

Island Time West – 353 Miramar

Island Time West is a stylishly remodeled townhome with 3 bedrooms, 3.5 bathrooms, and a sleeping capacity of 14. It includes a private heated pool and spa. There’s also a game room in the garage area with a ping pong table and foosball. Enjoy the beautiful weather on any of the multiple balconies or patio spaces. When you get out to explore, beaches, restaurants, and shops are just a quick walk or bike ride away! The house is located behind Ocean Boulevard, which is the main street of the village. And if you need more space, the property can be rented with Island Time East next door, which offers the same space and amenities. 

On the Rocks – 309 Miramar

For a beautiful elevated single-story pool home, look no further than On the Rocks. The home sleeps 15 with 5 bedrooms and 5 bathrooms. Hours of fun await the whole family in the large private heated pool and spa with water slide. There’s also a splash sun shelf covered patio, which features a pool table, refrigerator, and deep freezer. This is a great rental property for families with kids or anyone hosting a get-together.

Sugar Sand Cottage – 105 Beach

Are you hoping to wake up to gorgeous Gulf views? Sugar Sand Cottage may be the right rental for you. Watch stunning sunrises and sunsets from the comfort of your bedroom, covered patio, courtyard, or multiple decks and patios. The house includes 5 bedrooms and 3.5 bathrooms and is only steps away from Siesta Key Beach.