Apartment
10.0(171 Reviews)
1 Bedroom
2 Guests
Hot Tub
Parking
Ocean View
Balcony/Terrace
US $145/Night
7 Nights - US $1,013
Bermuda Winter Rentals & Holiday Homes
Discover winter rentals Bermuda - We found 169 exact matches
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Compare Winter Rental in Bermuda
10.0
Apartment
9.5(15 Reviews)
2 Bedrooms
4 Guests
EV Charge Station- Parking
Pool- Balcony/Terrace
US $400/Night
7 Nights - US $2,800
Bed & Breakfast
9.4(169 Reviews)
1 Bedroom
Breakfast- Balcony/Terrace
Kitchen
Air Conditioner
US $554/Night
7 Nights - US $3,878
Apartment
10.0(155 Reviews)
1 Bedroom
2 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $374/Night
7 Nights - US $2,616
Cottage
10.0(135 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
View
US $205/Night
7 Nights - US $1,436
Resort
9.3(22 Reviews)
50 Guests
Private Pool
Private Beach- Oceanfront
- Hot Tub
US $670/Night
7 Nights - US $4,693
Apartment
10.0(117 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $337/Night
7 Nights - US $2,360
Resort
9.1(76 Reviews)
6 Guests
- Private Beach
- Oceanfront
- Hot Tub
- Breakfast
US $671/Night
7 Nights - US $4,697
Apartment
10.0(114 Reviews)
1 Bedroom
3 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $219/Night
7 Nights - US $1,533
Resort
9.1(48 Reviews)
35 Guests
- Hot Tub
- Breakfast
- EV Charge Station
- Parking
US $793/Night
7 Nights - US $5,551
Cottage
10.0(107 Reviews)
1 Bedroom
3 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $295/Night
7 Nights - US $2,064
US $517/Night
7 Nights - US $3,619
Apartment
10.0(104 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $264/Night
7 Nights - US $1,846
Cottage
10.0(84 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $406/Night
7 Nights - US $2,843
House
10.0(52 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $651/Night
7 Nights - US $4,555
House
10.0(25 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $352/Night
7 Nights - US $2,462
Cottage
10.0(22 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $285/Night
7 Nights - US $1,993
Apartment
10.0(21 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $304/Night
7 Nights - US $2,130
House
10.0(19 Reviews)
8 Bedrooms
16 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $5,630/Night
7 Nights - US $39,413
Cottage
10.0(19 Reviews)
1 Bedroom
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $419/Night
7 Nights - US $2,932
Apartment
10.0(16 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $289/Night
7 Nights - US $2,021
House
10.0(13 Reviews)
5 Bedrooms
9 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $4,203/Night
7 Nights - US $29,421
US $2,048/Night
7 Nights - US $14,333
About Bermuda Winter Rental on Casai.nz
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 169 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 Bermuda Winter Rentals
What are the top rated Winter Rentals in Bermuda?
There are a lot of options in Bermuda. If you plan on staying in the Bermuda area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Bermuda:
- 2 Units Combined - Include private dock and Lovely Water Views
- Pembroke Villa - Business and Vacation Home
- Tranquil, Roomy Getaway - Close to City of Hamilton
- Luxury, Harbour View Gem In Historic St George's
- Coral Sea Oasis with private beach and infinity Pool
- Luxurious 4 Bedroom Oceanside house with pool
- 'RIPPLE WATERS' - More for Less - Great One Bedroom Pool House
- 2-bedroom cottage with 2 King beds, Private Pool, Full kitchen and Ocean views
- "MasterView" a Waterfront Retreat - Two Bedroom Cottage on the Sea
- Spacious Hilltop Retreat in Tuckerstown with Stunning Views, Newly Renovated
How much does it cost to rent a place to stay near Bermuda in the wintertime?
The average cost for winter rentals in Bermuda is $699 per night. Casai has a wide list of great winter places to stay near Bermuda that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Bermuda that allow pets?
Yes, here are the top cottage/chalet rentals in Bermuda that allow you to bring your pet or dog:
- Location! Location! AUTUMN SAVINGS at 5 Cross Bay Estate, next to Horseshoe Bay
- Frognal Apartment
- The Oxford House
- Spacious Beachfront and Private Resort living
See all pet-friendly vacation rentals in Bermuda on Casai.nz
Do you have any winter rentals in Bermuda that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Bermuda to find what works for you.
Are there winter accommodations in Bermuda that have indoor swimming pools?
As of 2026, the data from Casai.nz shows that there are over 169 private swimming pools or indoor pools accommodations near Bermuda along with other great amenities.
Do any winter holiday rentals in Bermuda have hot tubs?
About 169 holiday rentals in Bermuda boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Bermuda?
Yes, there are many luxury places to stay in Bermuda for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Bermuda with all the best amenities for your next trip.
