Apartment
10.0(390 Reviews)
1 Bedroom
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
R3,995/Night
7 Nights - R27,964
San Diego Winter Rentals & Holiday Homes
Discover winter rentals San Diego - We found 6189 exact matches
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Compare Winter Rental in San Diego
10.0
House
10.0(11 Reviews)
6 Bedrooms
15 Guests
Hot Tub- Parking
- Air Conditioner
Internet
R22,967/Night
7 Nights - R160,772
Apartment
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,461/Night
7 Nights - R24,233
House
10.0(365 Reviews)
1 Bedroom
2 Guests
Oceanfront- Parking
Ocean View- Balcony/Terrace
R7,462/Night
7 Nights - R52,230
Apartment
10.0(9 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
Breakfast
Pool
R3,264/Night
7 Nights - R22,851
Condo
10.0(289 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R5,785/Night
7 Nights - R40,489
House
10.0(6 Reviews)
5 Bedrooms
12 Guests
- Oceanfront
EV Charge Station- Parking
- Ocean View
R12,653/Night
7 Nights - R88,572
House
10.0(279 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R6,691/Night
7 Nights - R46,834
Villa
10.0(5 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R19,431/Night
7 Nights - R136,022
Apartment
10.0(268 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
R4,755/Night
7 Nights - R33,294
House
10.0(4 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
R16,272/Night
7 Nights - R113,904
House
10.0(217 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R3,757/Night
7 Nights - R26,298
House
10.0(4 Reviews)
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
View- Internet
R15,539/Night
7 Nights - R108,774
Apartment
10.0(179 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R3,684/Night
7 Nights - R25,782
House
10.0(166 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
R10,011/Night
7 Nights - R70,085
Condo
10.0(145 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R6,822/Night
7 Nights - R47,750
House
10.0(144 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
R7,593/Night
7 Nights - R53,146
House
10.0(144 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R6,662/Night
7 Nights - R46,634
Condo
10.0(139 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R7,731/Night
7 Nights - R54,112
House
10.0(137 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
R7,129/Night
7 Nights - R49,899
House
10.0(127 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R8,724/Night
7 Nights - R61,074
Condo
10.0(126 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R2,955/Night
7 Nights - R20,686
House
10.0(125 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,757/Night
7 Nights - R26,298
House
10.0(118 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R5,016/Night
7 Nights - R35,109
About San Diego Winter Rental on Casai.co.za
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 6189 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.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About San Diego Winter Rentals
What are the top rated Winter Rentals in San Diego?
There are a lot of options in San Diego. If you plan on staying in the San Diego area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in San Diego:
- Storybook Beach House 2 blocks from the Beach or Mission Bay with Pool & Hot tub
- Your Luxury Condo On The Ocean, Unobstructed Sunset And Ocean Views, Central Air
- Ocean Views - SEAGIRT RETREAT- 4 BD/4 BTH - Air Conditioning - Family Getaway
- VIEWS! VIEWS! VIEWS! 4 Master Suites 5 Star Architectural Designer with Spa
- Luxury Pacific Beach Family Getaway Steps to Beach Jacuzzi Yard AC Garage BBQ
- Oceanfront Luxury Condo, Sounds of the Surf, Beautiful Sunsets
- Stunning Remodel 4 BR/3 BA Downtown ,Gaslamp, Petco, Convention Center
- Wow! Private Pool and Spa Home w/Ocean/City Views, A/C, Fire Pit, Putting Green!
- Panoramic Ocean View Of Sunset Cliffs-Best View in Point Loma!
- Immaculate Beach House - 1 min walk to ocean, 2 unshared patios
How much does it cost to rent a place to stay near San Diego in the wintertime?
The average cost for winter rentals in San Diego is $553 per night. Casai has a wide list of great winter places to stay near San Diego that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in San Diego that allow pets?
Yes, here are the top cottage/chalet rentals in San Diego that allow you to bring your pet or dog:
- Spacious Beach Studio
- Balboa 6BR Mansion with Hot Tub and Game Room
- SD Getaway - Boho Studio, Spacious Yard w/BBQ
- 50' from Ocean - Amazing View - Private Cottage - Not a Condo
See all pet-friendly vacation rentals in San Diego on Casai.co.za
Do you have any winter rentals in San Diego that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in San Diego to find what works for you.
Are there winter accommodations in San Diego that have indoor swimming pools?
As of 2026, the data from Casai.co.za shows that there are over 6189 private swimming pools or indoor pools accommodations near San Diego along with other great amenities.
Do any winter holiday rentals in San Diego have hot tubs?
About 6189 holiday rentals in San Diego boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in San Diego?
Yes, there are many luxury places to stay in San Diego for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near San Diego with all the best amenities for your next trip.
