Villa
10.0(18 Reviews)
3 Bedrooms
6 Guests
Private Pool
Parking
Pool
Balcony/Terrace
CA $1,290/Night
7 Nights - CA $9,027
Anguilla Winter Rentals & Holiday Homes
Discover winter rentals Anguilla - We found 189 exact matches
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Compare Winter Rental in Anguilla
10.0
CA $552/Night
7 Nights - CA $3,861
CA $2,592/Night
7 Nights - CA $18,141
Villa
10.0(17 Reviews)
4 Bedrooms
8 Guests
- Private Pool
Oceanfront
Hot Tub- Parking
CA $4,360/Night
7 Nights - CA $30,517
House
10.0(5 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
Breakfast- Parking
- Balcony/Terrace
CA $376/Night
7 Nights - CA $2,635
Villa
10.0(16 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
Ocean View
CA $1,190/Night
7 Nights - CA $8,332
Resort
9.3(64 Reviews)
79 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
CA $1,285/Night
7 Nights - CA $8,995
Villa
10.0(9 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $4,007/Night
7 Nights - CA $28,049
Bed & Breakfast
9.0(3 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Balcony/Terrace
Air Conditioner
CA $132/Night
7 Nights - CA $922
House
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $462/Night
7 Nights - CA $3,232
CA $7,702/Night
7 Nights - CA $53,914
Condo
10.0(7 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
CA $313/Night
7 Nights - CA $2,194
CA $9,257/Night
7 Nights - CA $64,799
Villa
10.0(5 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Breakfast
- Parking
CA $5,794/Night
7 Nights - CA $40,558
CA $1,920/Night
7 Nights - CA $13,441
Villa
10.0(4 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $1,813/Night
7 Nights - CA $12,692
New
Condo
10.0(4 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
CA $1,721/Night
7 Nights - CA $12,043
Villa
10.0(4 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $1,532/Night
7 Nights - CA $10,724
Villa
10.0(3 Reviews)
6 Bedrooms
11 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
CA $10,070/Night
7 Nights - CA $70,493
New
Condo
10.0(3 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Breakfast
- Parking
- Ocean View
CA $1,298/Night
7 Nights - CA $9,083
Villa
10.0(2 Reviews)
9 Bedrooms
20 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $13,036/Night
7 Nights - CA $91,248
Villa
10.0(2 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
CA $9,010/Night
7 Nights - CA $63,071
Villa
10.0(2 Reviews)
6 Bedrooms
12 Guests
- Private Pool
- Pool
- Balcony/Terrace
View
CA $4,421/Night
7 Nights - CA $30,948
Villa
10.0(2 Reviews)
7 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $3,367/Night
7 Nights - CA $23,573
About Anguilla Winter Rental on Casai.ca
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 189 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 Anguilla Winter Rentals
What are the top rated Winter Rentals in Anguilla?
There are a lot of options in Anguilla. If you plan on staying in the Anguilla area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Anguilla:
- Tranquility Beach Anguilla
- Villa Farina in the Farrington
- Fortune Estate East (Rental Car Available)
- Sand Villa at Long Bay Villas: Ultra-luxury on the beach with 5-star service
- Stunning 3 Acre Estate with beach, pool + jacuzzi
- Infinity at Sheriva Villas/2 pools/2 Hot Tubs/2 Golf Carts-2 min. to Beach
- Infinity at Sheriva Villas/Ocean-view with 2 pools/2 Hot Tubs/Golf Cart
- Beaches Edge | Oceanfront Estate, Anguilla
- Dolphin at Anguillitta: 3BR Beachfront, Book Now!
- Luxury 1-Bedroom + Hot Tub at Award-Winning Tranquility Beach on Meads Bay Beach
How much does it cost to rent a place to stay near Anguilla in the wintertime?
The average cost for winter rentals in Anguilla is $3,560 per night. Casai has a wide list of great winter places to stay near Anguilla that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Anguilla that allow pets?
Yes, here are the top cottage/chalet rentals in Anguilla that allow you to bring your pet or dog:
- Ocean Front Villa In Island Harbour, Anguilla BWI
- Châlet Genesis
- Anguilla's Bird of Paradise
- ON THE BEACH Luxury BeachHouse, sleeps 8, pool, hot-tub, fire-pit, …
See all pet-friendly vacation rentals in Anguilla on Casai.ca
Do you have any winter rentals in Anguilla that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Anguilla to find what works for you.
Are there winter accommodations in Anguilla that have indoor swimming pools?
As of 2026, the data from Casai.ca shows that there are over 189 private swimming pools or indoor pools accommodations near Anguilla along with other great amenities.
Do any winter holiday rentals in Anguilla have hot tubs?
About 189 holiday rentals in Anguilla boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Anguilla?
Yes, there are many luxury places to stay in Anguilla for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Anguilla with all the best amenities for your next trip.
