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Winter Gardens Holiday Rentals

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Our top choices for Winter Gardens holiday rentals

1. Spacious 4-bedroom house with AC, fitness equipment in wonderful Lakeside

Spacious 4-bedroom house with AC, fitness equipment in wonderful Lakeside
Lakeside
9.6 out of 10, Exceptional, (7 reviews)
"From the check in process to the stay it was a great experience . The house was clean and well stocked with everything needed to enjoy our stay"
United States
Timothy C.
The price is AU$807
includes taxes & fees
15 Sept - 16 Sept
Spacious 4-bedroom house with AC, fitness equipment in wonderful Lakeside

2. Elegant Hillside Estate | Heated Pool+Sunset Views

Elegant Hillside Estate | Heated Pool+Sunset Views
El Cajon
The price is AU$1,223
includes taxes & fees
15 Sept - 16 Sept
Elegant Hillside Estate | Heated Pool+Sunset Views

3. Cozy Private Studio in El Cajon

Cozy Private Studio in El Cajon
Mount Helix
8.8 out of 10, Excellent, (29 reviews)
"It was a great plead to stay"
United States
Simon
The price is AU$206
includes taxes & fees
17 Sept - 18 Sept
Cozy Private Studio in El Cajon

4. Riviera Oaks Resort by Coolvacay

Riviera Oaks Resort by Coolvacay
3.0 star property
San Diego Country Estates
9.6 out of 10, Exceptional, (1,072 reviews)
"best place to relax, nice people"
United States
BO
The price is AU$185
includes taxes & fees
15 Sept - 16 Sept
Riviera Oaks Resort by Coolvacay

5. La Casita Guest House, private fenced yard & with heat and AC, pet friendly

La Casita Guest House, private fenced yard & with heat and AC, pet friendly
Mount Helix
9.8 out of 10, Exceptional, (13 reviews)
"Thank you so much for the hospitality and your kindness"
United States
Lisa D.
The price is AU$457
includes taxes & fees
19 Sept - 20 Sept
La Casita Guest House, private fenced yard & with heat and AC, pet friendly

6. La Mesa Family Retreat - 20 minutes to Beaches & More!

La Mesa Family Retreat - 20 minutes to Beaches & More!
La Mesa
9.0 out of 10, Wonderful, (11 reviews)
"The property was well located for us. "
United States
Ann D.
The price is AU$759
includes taxes & fees
15 Sept - 16 Sept
La Mesa Family Retreat - 20 minutes to Beaches & More!

7. Lake Murray 3BR Retreat with AC and Skylight

Lake Murray 3BR Retreat with AC and Skylight
La Mesa
10.0 out of 10, Exceptional, (16 reviews)
"Our stay was fantastic and it had everything we need for our 1 week stay. I recommend this location. "
United States
Rosa C.
The price is AU$400
includes taxes & fees
15 Sept - 16 Sept
Lake Murray 3BR Retreat with AC and Skylight

8. The Outside Inn at The Tipsy Goat Ranch

The Outside Inn at The Tipsy Goat Ranch
Lakeside
10.0 out of 10, Exceptional, (28 reviews)
"Host was fantastic. Property is exactly as described, unique place to stay and definitely memorable."
United States
Tom D.
The price is AU$412
includes taxes & fees
15 Sept - 16 Sept
The Outside Inn at The Tipsy Goat Ranch

9. Splendid 1-bedroom apartment in delightful La Mesa with AC and Laundry

Splendid 1-bedroom apartment in delightful La Mesa with AC and Laundry
Mid-City
10.0 out of 10, Exceptional, (7 reviews)
"This is probably the nicest place in which I have stayed in my thirty or so years of traveling to San Diego. And Rico was a superb host. But I didn’t have to ask him for much, as he provided an abundance of sundries and drinks. Highest recommendation."
United States
Peter
The price is AU$212
includes taxes & fees
30 Sept - 1 Oct
Splendid 1-bedroom apartment in delightful La Mesa with AC and Laundry

10. 'Ted' 2-bedroom cozy house in central location! 10 minutes to Balboa!

'Ted' 2-bedroom cozy house in central location! 10 minutes to Balboa!
Encanto
8.8 out of 10, Excellent, (39 reviews)
"Beds were very comfortable."
United States
Paula
The price is AU$351
includes taxes & fees
15 Sept - 16 Sept
'Ted' 2-bedroom cozy house in central location! 10 minutes to Balboa!

11. San Diego Country Estates

San Diego Country Estates
2.5 star property
San Diego Country Estates
9.4 out of 10, Exceptional, (297 reviews)
"Great stay!"
United States
Kelly
The price is AU$165
includes taxes & fees
20 Sept - 21 Sept
San Diego Country Estates

12. Luxury Hilltop Estate I Resort Pool + Sunset Views

Luxury Hilltop Estate I Resort Pool + Sunset Views
Rancho San Diego
9.8 out of 10, Exceptional, (21 reviews)
"We had a fantastic time, highly recommend staying that this property! "
United States
Alex E.
The price is AU$1,440
includes taxes & fees
21 Sept - 22 Sept
Luxury Hilltop Estate I Resort Pool + Sunset Views

13. Uptown Inn by Vantaggio - Limited Service Apart-Hotel

Uptown Inn by Vantaggio - Limited Service Apart-Hotel
2.5 star property
Hillcrest
8.4 out of 10, Very good, (460 reviews)
"Room was perfect for our short trip. Clean room and friendly staff."
United States
Diana
The price is AU$155
includes taxes & fees
30 Sept - 1 Oct
Uptown Inn by Vantaggio - Limited Service Apart-Hotel

14. Canyon View Tranquil Oasis, Private Pool and Dreamy Sunsets, New Backyard

Canyon View Tranquil Oasis, Private Pool and Dreamy Sunsets, New Backyard
San Carlos
9.4 out of 10, Exceptional, (70 reviews)
"Communication with the host was excellent. Very nice home with a beautiful pool. Would visit again"
United States
Mary N.
The price is AU$954
includes taxes & fees
23 Sept - 24 Sept
Canyon View Tranquil Oasis, Private Pool and Dreamy Sunsets, New Backyard

15. Cozy 2-Bedroom Cottage Near Balboa Park

Cozy 2-Bedroom Cottage Near Balboa Park
Mid-City
8.8 out of 10, Excellent, (12 reviews)
"Overall it was a great place to stay."
United States
Cristal M.
The price is AU$423
includes taxes & fees
17 Sept - 18 Sept
Cozy 2-Bedroom Cottage Near Balboa Park

16. Hideaway in the heart of San Diego!

Hideaway in the heart of San Diego!
Mid-City
9.8 out of 10, Exceptional, (10 reviews)
"Very pet friendly. Parking right behind the house. Overall excellent stay."
United States
Lisa S.
The price is AU$487
includes taxes & fees
15 Sept - 16 Sept
Hideaway in the heart of San Diego!

17. Jamul's Jewel: 10ACRES,Hilltop,Heated*Salt Pool,Spa*,City & Mtn.Views,B-Ball Court*,Grill,Horseshoes

Jamul's Jewel: 10ACRES,Hilltop,Heated*Salt Pool,Spa*,City & Mtn.Views,B-Ball Court*,Grill,Horseshoes
Jamul
9.6 out of 10, Exceptional, (59 reviews)
"Great stay"
United States
Carson M.
The price is AU$662
includes taxes & fees
17 Sept - 18 Sept
Jamul's Jewel: 10ACRES,Hilltop,Heated*Salt Pool,Spa*,City & Mtn.Views,B-Ball Court*,Grill,Horseshoes

18. Villa Del Cerro

Villa Del Cerro
Del Cerro
9.4 out of 10, Exceptional, (28 reviews)
"We had a great stay. Beautiful home with lots of activities. Great for a family reunion or retirement gathering. Would love to stay here again! "
United States
Tera F.
The price is AU$1,258
includes taxes & fees
16 Sept - 17 Sept
Villa Del Cerro

19. Hilltop cabin with panoramic lake & mountain views

Hilltop cabin with panoramic lake & mountain views
Del Dios
9.6 out of 10, Exceptional, (55 reviews)
"I loved how unique and cute this stay was"
United States
Kayla
The price is AU$273
includes taxes & fees
15 Sept - 16 Sept
Hilltop cabin with panoramic lake & mountain views

20. Little Italy Inn - Limited Service Apart Hotel

Little Italy Inn - Limited Service Apart Hotel
2.5 star property
Downtown San Diego
8.4 out of 10, Very good, (298 reviews)
"Very close to little Italy with tons of good food."
United States
Laura
The price is AU$158
includes taxes & fees
21 Sept - 22 Sept
Little Italy Inn - Limited Service Apart Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Gardens Hotel Reviews

Find out more about Winter Gardens

Everything you need to know about Winter Gardens holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Gardens holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Gardens holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winter Gardens holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Gardens. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winter Gardens holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winter Gardens holiday rentals we have selected for you start as low as AU$154 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winter Gardens rentals

At Expedia, we put the best Winter Gardens holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winter Gardens rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Gardens holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Gardens. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Winter Gardens?

Yes, we give you a choice of holiday rentals where you'll be just 14.3 mi (22.9 km) from San Diego Zoo, offering you a more secluded option to escape the hustle and bustle.

What are some of the best holiday rentals that Winter Gardens has to offer?

3 Story Spanish Style House, Best Location in SD. Views of North Park, With AC: This holiday home rental outside of Winter Gardens is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Winter Gardens?

Choose from 5 Expedia holiday rentals in Winter Gardens for a memorable holiday.

What can I see and do in Winter Gardens?

Explore the area and family-friendly sights such as San Diego Zoo, or get out into nature at a spot like Balboa Park. Petco Park and Marine Corps Recruit Depot are other popular places to visit in the area.

What are holiday rentals like in Winter Gardens?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Gardens. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.