Villa
10.0(70 Reviews)
3 Bedrooms
5 Guests
Private Pool
Oceanfront
Parking
Pool
US $326/Night
7 Nights - US $2,282
Tryall Winter Rentals & Holiday Homes
Discover winter rentals Tryall - We found 127 exact matches
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Compare Winter Rental in Tryall
10.0
Resort
8.3(18 Reviews)
104 Guests
Private Beach- Oceanfront
Breakfast- Parking
US $515/Night
7 Nights - US $3,606
US $94/Night
7 Nights - US $658
Villa
10.0(54 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $1,254/Night
7 Nights - US $8,780
Villa
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Private Pool
Hot Tub- Pool
Balcony/Terrace
US $1,460/Night
7 Nights - US $10,223
Villa
10.0(2 Reviews)
6 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $4,297/Night
7 Nights - US $30,081
Villa
10.0(2 Reviews)
6 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $3,721/Night
7 Nights - US $26,044
Villa
10.0(2 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $2,994/Night
7 Nights - US $20,961
Villa
10.0(2 Reviews)
7 Bedrooms
14 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
US $802/Night
7 Nights - US $5,616
Villa
9.8(20 Reviews)
3 Bedrooms
5 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $326/Night
7 Nights - US $2,282
Villa
7.4(3 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,722/Night
7 Nights - US $12,057
Villa
6.0(1 Review)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Pool
Ocean View
US $2,150/Night
7 Nights - US $15,049
US $9,593/Night
7 Nights - US $67,150
New
House
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $7,310/Night
7 Nights - US $51,171
US $5,611/Night
7 Nights - US $39,277
US $5,374/Night
7 Nights - US $37,620
US $5,097/Night
7 Nights - US $35,682
US $4,929/Night
7 Nights - US $34,503
US $4,701/Night
7 Nights - US $32,907
US $4,632/Night
7 Nights - US $32,426
US $4,583/Night
7 Nights - US $32,078
US $4,536/Night
7 Nights - US $31,751
US $4,284/Night
7 Nights - US $29,991
US $4,197/Night
7 Nights - US $29,381
About Tryall Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 127 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
Frequently Asked Questions About Tryall Winter Rentals
What are the top rated Winter Rentals in Tryall?
There are a lot of options in Tryall. If you plan on staying in the Tryall area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Tryall:
- Pineapple House Luxury villa
- Phoenix (5/7 Rooms) Luxury villa
- Bumper's Nest Luxury villa
- Point of View Luxury villa
- Quinntessential Luxury villa
- 5br Oceanfront Contemporary Round Hill Resort Villa Beach Pickleball Spa Gym
- Beautiful Sunset Luxury villa
- Beautiful Trinity Luxury villa
- Bougainvillea House Luxury villa
- Round House Luxury villa
How much does it cost to rent a place to stay near Tryall in the wintertime?
The average cost for winter rentals in Tryall is $3,302 per night. Casai has a wide list of great winter places to stay near Tryall that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Tryall that allow pets?
Yes, here are the top cottage/chalet rentals in Tryall that allow you to bring your pet or dog:
- Free Airport pick-up. private villa with amazing ocean veiw, pool, and maid.
- Round Hill Hotel & Villas
- Sky Beach Rooms
- Allamanda Villa- Tryall Resort Membership- van/driver- nanny
See all pet-friendly vacation rentals in Tryall on Casai.com
Do you have any winter rentals in Tryall that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Tryall to find what works for you.
Are there winter accommodations in Tryall that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 127 private swimming pools or indoor pools accommodations near Tryall along with other great amenities.
Do any winter holiday rentals in Tryall have hot tubs?
About 127 holiday rentals in Tryall boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Tryall?
Yes, there are many luxury places to stay in Tryall for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Tryall with all the best amenities for your next trip.
