Sarasota Winter Rentals & Holiday Homes
Discover winter rentals Sarasota - We found 4120 exact matches
When do you want to travel?
- Air Conditioner
- Parking
- Pool
- Parking
- Pool
- Wheelchair Accessible
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Parking
- Pool
- Child Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Frequently Asked Questions About Sarasota Winter Rental
What are the top rated Winter Rentals in Sarasota?
There are a lot of options in Sarasota. If you plan on staying in the Sarasota area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Sarasota:
- Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
- Beachfront Condo, Newly renovated! Heated Pool on the beach. GulfView 102.
- 4 Bedroom, 2 Bath. Heated Pool & Spa! Close to Beaches!
- BEACH NEST IS GETTING A RENOVATION! WE WILL BE BACK! CHECK BACK FOR UPDATES! XOX
- Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to beach!
- Dragonfly - Southern charm on the North end of Anna Maria Island
- Weekly Discounts! Exceptional Rating-A Pearl of a Beach Home- private pool & spa
- Walk To Siesta Village And Beach/Private Heated Pool & Hot Tub
- Palm Bay Club #168 Private beach perfect for a Staycation/recently updated
- Spectacular Beachfront House with Pool
How much does it cost to rent a place to stay near Sarasota in the wintertime?
The average cost for winter rentals in Sarasota is $695 per night. Hottubhomes has a wide list of great winter places to stay near Sarasota that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Sarasota that allow pets?
Yes, here are the top cottage/chalet rentals in Sarasota that allow you to bring your pet or dog:
- Are you ready for a luxury 5-floor penthouse 60 ft from water, 150 reviews
- Sandy Shore 5157
- Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub
- Blue Water Beach House: 5+ bdrm, 4.5 bath, Heated Pool/spa, 1.5 blocks to beach
See all pet-friendly vacation rentals in Sarasota on Hottubhomes
Do you have any winter rentals in Sarasota that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Sarasota to find what works for you.
Are there winter accommodations in Sarasota that have indoor swimming pools?
As of 2026, the data from Hottubhomes shows that there are over 4120 private swimming pools or indoor pools accommodations near Sarasota along with other great amenities.
