Discover winter rentals Surfside - We found 756 exact matches
About Surfside Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Surfside, FL perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Surfside. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Surfside and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Surfside Winter Rentals
What are the top rated Winter Rentals in Surfside?
There are a lot of options in Surfside. If you plan on staying in the Surfside area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Surfside:
- SANDCASTLES OCEAN VIEW TOP FLOOR.DATES AVAILABLE (check Reviews)
- Pool/Beach View Condo
- Beachfront Condo
- SANDCASTLES DIRECT OCEANFRONT CONDO-FALL, WINTER, FEBRUARY, MARCH 2026 AVAILABLE
- CK our super low rates for the fall in this 3 bedroom 2 bath direct ocean front
- Beautiful Oceanfront Condominium
- DIRECT OCEANFRONT NOW RENTING SUMMER FALL AND WINTER! BEAUTIFUL OCEANFRONT VIEW!
- 4th Floor Direct Ocean Front Corner Condo With Fantastic views & reviews
- SANDCASTLES 201 LUXURIOUS VACATION RETREAT Read Our Reviews!
- Direct Ocean, 3 bdrm 2 bathrm condo, wrap around balcony, WIFi, beautiful
How much does it cost to rent a place to stay near Surfside in the wintertime?
The average cost for winter rentals in Surfside is $367 per night. Vacation Cottage has a wide list of great winter places to stay near Surfside that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Surfside that allow pets?
Yes, here are the top cottage/chalet rentals in Surfside that allow you to bring your pet or dog:
- Family-Friendly Beach House – Private Pool, Balcony, BBQ Grills & Prime Location!
- *Ocean Oasis: Beach Extras & Bikes & Surfboards*
- Sandcastles by Happy Palm Stays
- Salt + Sol Cocoa Beach
See all pet-friendly vacation rentals in Surfside on Vacation Cottage
Do you have any winter rentals in Surfside that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Surfside to find what works for you.
Are there winter accommodations in Surfside that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 756 private swimming pools or indoor pools accommodations near Surfside along with other great amenities.
Do any winter holiday rentals in Surfside have hot tubs?
About 756 holiday rentals in Surfside boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Surfside?
Yes, there are many luxury places to stay in Surfside for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Surfside with all the best amenities for your next trip.
