Villa
10.0(111 Reviews)
2 Bedrooms
4 Guests
Oceanfront
Parking
Pool
Ocean View
US $436/Night
7 Nights - US $3,050
Treasure Island Winter Rentals & Holiday Homes
Discover winter rentals Treasure Island - We found 1462 exact matches
- Up-front pricing
- No markup
- Trusted partners
Compare Winter Rental in Treasure Island
10.0
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
Hot Tub- Parking
- Pool
View
US $352/Night
7 Nights - US $2,464
US $371/Night
7 Nights - US $2,600
Villa
10.0(99 Reviews)
2 Bedrooms
4 Guests
Private Pool- Parking
- Pool
- Ocean View
US $430/Night
7 Nights - US $3,010
House
10.0(3 Reviews)
1 Bedroom
6 Guests
- Oceanfront
- Hot Tub
- Ocean View
- View
US $282/Night
7 Nights - US $1,973
Condo
10.0(82 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
Balcony/Terrace
US $236/Night
7 Nights - US $1,652
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- View
US $415/Night
7 Nights - US $2,905
Condo
10.0(79 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $404/Night
7 Nights - US $2,825
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- View
US $351/Night
7 Nights - US $2,457
Condo
10.0(76 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $274/Night
7 Nights - US $1,919
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- View
US $351/Night
7 Nights - US $2,457
Cottage
10.0(76 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $219/Night
7 Nights - US $1,531
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Ocean View
- View
US $282/Night
7 Nights - US $1,973
Condo
10.0(75 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $379/Night
7 Nights - US $2,654
Condo
10.0(66 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $311/Night
7 Nights - US $2,180
Condo
10.0(64 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $312/Night
7 Nights - US $2,182
Condo
10.0(60 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $387/Night
7 Nights - US $2,707
Condo
10.0(56 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $252/Night
7 Nights - US $1,766
House
10.0(55 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $417/Night
7 Nights - US $2,920
House
10.0(53 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $573/Night
7 Nights - US $4,012
Condo
10.0(53 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $223/Night
7 Nights - US $1,564
Condo
10.0(50 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $273/Night
7 Nights - US $1,910
New
Condo
10.0(49 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $203/Night
7 Nights - US $1,418
House
10.0(48 Reviews)
1 Bedroom
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $507/Night
7 Nights - US $3,548
About Treasure Island Winter Rental on BedroomVillas
At BedroomVillas, we feature a wide range of listings for accommodations in Treasure Island, FL that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. BedroomVillas winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you are escaping the snow or running to it, BedroomVillas helps connect you to the best cabins, bungalows, lodges, and villas, as well as the best places to stay in both sun and ski resorts. BedroomVillas will make your winter getaway an unforgettable experience.
BedroomVillas offers luxury finds for travelers planning on renting a place in Treasure Island, to enjoy these benefits and to book your winter vacation homes, go to the BedroomVillas filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Treasure Island and unlock even more amazing deals. Relax with BedroomVillas.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Treasure Island Winter Rentals
What are the top rated Winter Rentals in Treasure Island?
There are a lot of options in Treasure Island. If you plan on staying in the Treasure Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Treasure Island:
- Spectacular Oceanfront condo on the Sands of Treasure Island
- Saint Petersburg/Treasure Island Ocean Front Beach Resort
- Pure luxury at #Sunset Wave on the Beach
- Spacious 2 story condo, clean decor 3BR, 2.5 BA. 2 Floors, Pool Waterfront
- Cute.Comfortable.Convenient
- 🐚BBR #10, Steps to the Beach, HTD Pool, Lrg Rm w/Living Rm, Kitchen & 4 Beds!
- New Listing Sunset Tropical Beach Bungallow
- 1950s Retro 3 Bedroom/2 Bath Beach House w/Amazing Deck! John's Pass Gulf-Blvd
- UPDATED OCEANFRONT 2BR SUITE 405N TREASURE ISLAND RESORT GULF VIEW SUNSETVISTAS
- Gulf Views Heated Spa Steps to Beach
How much does it cost to rent a place to stay near Treasure Island in the wintertime?
The average cost for winter rentals in Treasure Island is $409 per night. BedroomVillas has a wide list of great winter places to stay near Treasure Island that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Treasure Island that allow pets?
Yes, here are the top cottage/chalet rentals in Treasure Island that allow you to bring your pet or dog:
- Hidden Gem! Treasure Island Waterfront 2/2 with a pool and dock!
- Land's End 3-305 Bay Front - Premier
- Crystal Palms Beach Resort
- Million Dollar Views! Waterfront 2 bedroom/2 bath duplex with pool and dock.
See all pet-friendly vacation rentals in Treasure Island on BedroomVillas
Do you have any winter rentals in Treasure Island that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Treasure Island to find what works for you.
Are there winter accommodations in Treasure Island that have indoor swimming pools?
As of 2026, the data from BedroomVillas shows that there are over 1462 private swimming pools or indoor pools accommodations near Treasure Island along with other great amenities.
Do any winter holiday rentals in Treasure Island have hot tubs?
About 1462 holiday rentals in Treasure Island boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Treasure Island?
Yes, there are many luxury places to stay in Treasure Island for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Treasure Island with all the best amenities for your next trip.
