Villa
10.0(108 Reviews)
3 Bedrooms
6 Guests
Oceanfront
Parking
Ocean View
Balcony/Terrace
CA $677/Night
7 Nights - CA $4,741
Breakers Winter Rentals & Holiday Homes
Discover winter rentals Breakers - We found 43 exact matches
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Compare Winter Rental in Breakers
10.0
CA $1,992/Night
7 Nights - CA $13,943
Apartment
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
Pool- Ocean View
CA $839/Night
7 Nights - CA $5,874
Villa
10.0(80 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
Hot Tub- Parking
- Ocean View
CA $571/Night
7 Nights - CA $3,993
House
4 Bedrooms
10 Guests
- Parking
- Pool
Kitchen
Air Conditioner
CA $1,792/Night
7 Nights - CA $12,545
Apartment
10.0(77 Reviews)
3 Bedrooms
7 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
CA $681/Night
7 Nights - CA $4,765
CA $1,135/Night
7 Nights - CA $7,942
Condo
10.0(57 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $655/Night
7 Nights - CA $4,582
Cottage
10.0(45 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $727/Night
7 Nights - CA $5,087
House
10.0(16 Reviews)
4 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $941/Night
7 Nights - CA $6,585
Villa
10.0(15 Reviews)
5 Bedrooms
17 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $1,908/Night
7 Nights - CA $13,358
House
10.0(9 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $669/Night
7 Nights - CA $4,680
Condo
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $492/Night
7 Nights - CA $3,445
House
10.0(4 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $2,547/Night
7 Nights - CA $17,828
Condo
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $518/Night
7 Nights - CA $3,623
House
10.0(1 Review)
5 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $7,884/Night
7 Nights - CA $55,188
Villa
10.0(1 Review)
6 Bedrooms
18 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $7,696/Night
7 Nights - CA $53,876
House
10.0(1 Review)
3 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $2,606/Night
7 Nights - CA $18,244
House
10.0(1 Review)
6 Bedrooms
18 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,789/Night
7 Nights - CA $12,524
Villa
9.8(35 Reviews)
5 Bedrooms
11 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,971/Night
7 Nights - CA $13,796
Condo
9.8(33 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
CA $398/Night
7 Nights - CA $2,787
House
9.6(27 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,725/Night
7 Nights - CA $12,072
House
9.6(19 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $803/Night
7 Nights - CA $5,622
House
9.0(2 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,457/Night
7 Nights - CA $10,198
About Breakers Winter Rental on Casai.ca
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 43 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 Breakers Winter Rentals
What are the top rated Winter Rentals in Breakers?
There are a lot of options in Breakers. If you plan on staying in the Breakers area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Breakers:
- Silver Reef 1 Luxury 2BR Beachfront Retreat with Pool
- KiToCay: Modern Beach House w/Over-the-Water Sun Deck & Private Beach Lot
- Piece of Mine Yellow: Beach Cottage on 200-feet of Shoreline w/Reef Snorkeling + Seaside Hammocks
- Old Man Bay Villa #2 - Modern, One Bedroom Villas
- Hidden Treasure by Grand Cayman Villas
- Piece of Mine Green: Beach Cottage on 200-feet of Shoreline w/Screened Porch, Snorkeling + Hammocks
- Old Man Bay Villa #1 - Modern, One Bedroom Villas
- Christmas Palms: Serene Villa with an Oceanfront Pool and Private Beach
- Jasmine Cottage: Shore Diver's Paradise w/Private Pool & Backyard Snorkeling
- Piece of Mine Blue: Beach Cottage on 200-feet of Shoreline w/Screened Porch, Snorkeling + Hammocks
How much does it cost to rent a place to stay near Breakers in the wintertime?
The average cost for winter rentals in Breakers is $2,086 per night. Casai has a wide list of great winter places to stay near Breakers that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Breakers that allow pets?
Yes, here are the top cottage/chalet rentals in Breakers that allow you to bring your pet or dog:
- Azure Breeze 3! Peaceful & Pristine-3Bd, 3 BATH AWAY from crowds! Beachfront!
- Halcyon Point
- Silver Reef Residencies
- BEAUTIFUL 3 BEDROOM VILLA LOCATED DIRECTLY ON THE BEACH, EXCELLENT SNORKELING
See all pet-friendly vacation rentals in Breakers on Casai.ca
Do you have any winter rentals in Breakers that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Breakers to find what works for you.
Are there winter accommodations in Breakers that have indoor swimming pools?
As of 2026, the data from Casai.ca shows that there are over 43 private swimming pools or indoor pools accommodations near Breakers along with other great amenities.
Do any winter holiday rentals in Breakers have hot tubs?
About 43 holiday rentals in Breakers boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Breakers?
Yes, there are many luxury places to stay in Breakers for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Breakers with all the best amenities for your next trip.
