Best Siesta Key Rentals for Winter

Siesta Key is one of the most beautiful spots in Florida, and it remains one of the state’s most well-kept secrets.

You will experience the luxury and relaxation you need from your getaway, and you won’t be bombarded with tons of crowds.

Planning a visit to Siesta Key in the winter will still provide tons of fun in the sun, but you will experience the off-season of the island, which lends itself to even fewer crowds and some amazing winter events. You can still enjoy these 5 unforgettable things to do on vacation and so much more!

Read on for some of our most popular Siesta Key vacation rentals for the winter.

Siesta Palooza

Large groups will love this 8-bed, 8-bath property that is just steps away from downtown Siesta Key. This brand-new luxury home is easy to navigate thanks to the elevator, so you can quickly get to the arcade room, full kitchen, or rooftop deck. Take advantage of the heated resort pool on those cold winter evenings, and enjoy our Professional Linen Program and Property Manager Program for all of your needs during your stay.

The Pool House

This 5-bed, 4-bath home is great for groups of up to 16. Inside, you’ll find amenities like laundry facilities, HDTVs, and gorgeous fixtures and appliances. Then head outside for a barbecue grill, private tiki hut, and heated pool and spa. This family home is breathtaking and cozy both inside and out.

Bahama Mama

You will experience the perfect combination of modern and quaint in this 5-bed, 5-bath home. Your entertaining space and covered patios provide gorgeous views of Siesta Key, and you’re just steps away from the village and the beach. Enjoy laundry facilities, convenient parking, and special features like preferred vendor discounts and our Property Manager Program. 

Island House

In this 7-bed, 6-bath home, your whole family will be able to truly escape the hustle and bustle of everyday life. Every level of the home provides beautiful views of the Gulf, and you all can spend time together inside in the spacious living and dining areas. This property truly shines on the outside, since you are just one block to the beach! Visit the canal across the street to paddleboard or fish, or hang out at the heated resort pool with a swim-up bar, jacuzzi, and more.

Summer House

Perfect for family reunions or wedding party, this 6-bed, 6-bath home comfortably sleeps 22 people! You’re less than a 2-minute walk to the beach and the village, and your preferred vendor discounts will help you get everything you need. Enjoy your covered porch and patio, take care of everyone’s laundry in the washer and dryer in your home, and lounge in the spacious living and kitchen areas.

About Siesta Key Luxury Rental Properties

We are proud to offer Siesta Key beach rentals that will fit your entire family and will help you create lasting memories together. Our rentals come standard with incredible amenities and programs for your convenience. You will find beach chairs and towels included with your rental, and for anything else, you will have access to our preferred vendor discounts. 

Our Professional Linen Program eliminates your need to bring towels, washcloths, or bed sheets, and the Property Manager Program gives you a one-on-one relationship with our staff. Whether you need something for your rental or you just want a dinner recommendation, we’ve got you covered! If you don’t want to leave your property, you can even order groceries online and have them delivered!

What to Do in the Winter

Even though it’s the off-season, there are still tons of fun events in Siesta Key for Christmas. Come out to the holiday parade, pick up a gift at the SantaFest and Holiday Gift Market, or join in on an Ugly Sweater Crawl. Siesta Key and the surrounding area provide so much to do in the winter months, so the whole family can get in on the fun.

Winter is the perfect time to vacation in Siesta Key. We have everything you would need, from Siesta Key rentals with private pools to pet-friendly rentals for your furry friend. For more information on all of our luxury vacation homes, contact us today!


Siesta Key Luxury Rental Properties
5111 Ocean Blvd. Suite B, C & D
Siesta Key, Florida USA 34242
#SiestaKeyLuxury #iHeartSiestaKey
VRMA MemberTrip Advisor Badge