Sarasota Winter Rentals & Holiday Homes

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:

• Carlisle Inn
• Across The Street From #1 Beach
• Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
• Immaculate, 3 bedroom, 2 bath Close to Siesta Beach, with HEATED POOL
• Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
• Beautiful, Gulf-Front Home on Bean Point-Halcyon House
• Beachfront Condo, Newly renovated! Heated Pool on the beach. GulfView 102.
• A Bayside Treasure - Outstanding Waterfront Views!
• Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
• 4 Bedroom, 2 Bath. Heated Pool & Spa! Close to Beaches!

The average cost for winter rentals in Sarasota is $534 per night. Ownerdirect 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.

Yes, here are the top cottage/chalet rentals in Sarasota that allow you to bring your pet or dog:

• Private Heated Pool - 100 Steps to Beach Access - 5-min walk to Siesta Key Village
• Beach & Bay by Beach Boutique Rentals
• Lulu's Key House Kemp Ridley 1/1 Downstairs
• Las Hermanas 1

See all pet-friendly vacation rentals in Sarasota on Ownerdirect

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.

As of 2026, the data from Ownerdirect shows that there are over 12106 private swimming pools or indoor pools accommodations near Sarasota along with other great amenities.