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Winter Gardens Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winter Gardens vacation rentals

Private kitchen

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.
$581 nightly
The price is $600
Nov 3 - Nov 4
Total with taxes and fees
Spacious 4-bedroom house with AC, fitness equipment in wonderful Lakeside
A two-story house with a swimming pool, lounge chairs, and a hot tub.

2. Entire Private House with 7 Beds, Pool, Hot Tub, Garage, Gated Yard, Arcade

Entire Private House with 7 Beds, Pool, Hot Tub, Garage, Gated Yard, Arcade
Lakeside
$494 nightly
The price is $530
Nov 4 - Nov 5
Total with taxes and fees
Entire Private House with 7 Beds, Pool, Hot Tub, Garage, Gated Yard, Arcade
Lobby

3. Riviera Oaks Resort by Coolvacay

Riviera Oaks Resort by Coolvacay
3.0 star property
San Diego Country Estates
9.6 out of 10, Exceptional, (1,106 reviews)
"Beautiful and cozy property!"
United States
Kristin
$107 nightly
The price is $121
Nov 1 - Nov 2
Total with taxes and fees
Riviera Oaks Resort by Coolvacay
A room with a dining table, chairs, a fan, and a closed door.

4. Cozy Private Studio in El Cajon

Cozy Private Studio in El Cajon
Mount Helix
8.8 out of 10, Excellent, (29 reviews)
"The host was very helpful"
United States
Bri S.
$133 nightly
The price is $133
Oct 29 - Oct 30
Total with taxes and fees
Cozy Private Studio in El Cajon
A well-maintained garden with various plants and a lawn, surrounded by multi-story buildings with balconies.

5. San Diego Country Estates

San Diego Country Estates
2.5 star property
San Diego Country Estates
9.4 out of 10, Exceptional, (312 reviews)
"This was the perfect location for me during my visit with my daughters. I will for sure be looking to stay here again in my next visits."
United States
Charles
$118 nightly
The price is $131
Oct 29 - Oct 30
Total with taxes and fees
San Diego Country Estates
A deck with two wicker chairs and a small table, overlooking a mountainous landscape and a body of water.

6. Luxury Studio with Lake Views and Spacious Balcony

Luxury Studio with Lake Views and Spacious Balcony
Spring Valley
8.0 out of 10, Very good, (8 reviews)
"Great place"
United States
Brian
$190 nightly
The price is $196
Nov 2 - Nov 3
Total with taxes and fees
Luxury Studio with Lake Views and Spacious Balcony
A living room with a beige sofa, two armchairs, a coffee table, and a rug. There are two lamps, a painting on the wall, and a window with a view of greenery and a blue car outside.

7. '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, (43 reviews)
"Beds were very comfortable."
United States
Paula
$222 nightly
The price is $247
Oct 29 - Oct 30
Total with taxes and fees
'Ted' 2-bedroom cozy house in central location! 10 minutes to Balboa!
A spacious lobby with a sofa, chairs, a bookshelf, and a large window with a view of greenery.

8. 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, (502 reviews)
"It was super clean and smooth easy check in and out process!"
United States
Aviana
$102 nightly
The price is $115
Oct 29 - Oct 30
Total with taxes and fees
Uptown Inn by Vantaggio - Limited Service Apart-Hotel
A modern lobby with a green sofa, a wooden accent wall, and a large plant.

9. 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, (383 reviews)
"Great stay nice staff"
United States
Olivia
$108 nightly
The price is $124
Nov 3 - Nov 4
Total with taxes and fees
Little Italy Inn - Limited Service Apart Hotel
A modern kitchen with a skylight, a dining area with a round table, and a ceiling fan.

10. Lake Murray 3BR Retreat with AC and Skylight

Lake Murray 3BR Retreat with AC and Skylight
La Mesa
10.0 out of 10, Exceptional, (17 reviews)
"Our stay was fantastic and it had everything we need for our 1 week stay. I recommend this location. "
United States
Rosa C.
$324 nightly
The price is $324
Nov 4 - Nov 5
Total with taxes and fees
Lake Murray 3BR Retreat with AC and Skylight
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

11. 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, (8 reviews)
"Our stay was lovely at Neric's place. Nice decor, clean, comfortable, & quiet. The AC worked well to keep the home at the perfect temp for us. We will stay here again!"
United States
Katherine S.
$156 nightly
The price is $156
Nov 3 - Nov 4
Total with taxes and fees
Splendid 1-bedroom apartment in delightful La Mesa with AC and Laundry
A pool with a waterfall feature, surrounded by lounge chairs and a patio area.

12. The Outside Inn at The Tipsy Goat Ranch

The Outside Inn at The Tipsy Goat Ranch
Lakeside
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful stay! Beautiful property and awesome staff! We would love to come back!"
United States
Angela
$298 nightly
The price is $298
Nov 3 - Nov 4
Total with taxes and fees
The Outside Inn at The Tipsy Goat Ranch
A narrow, enclosed walkway with wooden railings and a metal grid barrier, leading to a building entrance.

13. City24 Hotel Little Italy Mission Hills

City24 Hotel Little Italy Mission Hills
4.5 star property
Middletown
9.6 out of 10, Exceptional, (236 reviews)
"Friendly staff!"
United States
Donavin
$157 nightly
The price is $177
Nov 2 - Nov 3
Total with taxes and fees
City24 Hotel Little Italy Mission Hills
A spacious lounge area with a sofa, a coffee table, and a bar with stools.

14. Marriott Vacation Club®, San Diego

Marriott Vacation Club®, San Diego
3.5 star property
Downtown San Diego
9.4 out of 10, Exceptional, (1,256 reviews)
"Great for traveling families."
United States
Veronica Dangerfield
$144 nightly
The price is $167
Nov 10 - Nov 11
Total with taxes and fees
Marriott Vacation Club®, San Diego
87810974-5f2a-4191-9890-d2a532a8539e

15. Luxury Vineyard Escape w Fireplace - Malbec

Luxury Vineyard Escape w Fireplace - Malbec
San Diego County
10.0 out of 10, Exceptional, (3 reviews)
"The property was very nice and comfy, the views were beautiful, similar to the photos, though our stay was at Christmas. Pet friendly, a great location relative to the general Ramona area. Directions to property and accessing it were clear and detailed."
United States
A B.
$220 nightly
The price is $232
Nov 22 - Nov 23
Total with taxes and fees
Luxury Vineyard Escape w Fireplace - Malbec
A modern hotel room with a large bed, a bedside table, a built-in TV, and a shower area.

16. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
La Mesa
10.0 out of 10, Exceptional, (54 reviews)
"Beds were soft but supportive, good rest every night!"
United States
Anonymous traveler
$97 nightly
The price is $107
Nov 1 - Nov 2
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A room with a view of a lake and mountains. There is a wooden deck outside with a chair and a table.

17. Hilltop cabin with panoramic lake & mountain views

Hilltop cabin with panoramic lake & mountain views
Del Dios
9.6 out of 10, Exceptional, (61 reviews)
"I loved how unique and cute this stay was"
United States
Kayla
$196 nightly
The price is $196
Nov 2 - Nov 3
Total with taxes and fees
Hilltop cabin with panoramic lake & mountain views
A patio with outdoor furniture, a pathway, and a fence.

18. Cozy 2-Bedroom Cottage Near Balboa Park

Cozy 2-Bedroom Cottage Near Balboa Park
Mid-City
8.8 out of 10, Excellent, (13 reviews)
"Overall it was a great place to stay."
United States
Cristal M.
$270 nightly
The price is $300
Nov 2 - Nov 3
Total with taxes and fees
Cozy 2-Bedroom Cottage Near Balboa Park
A landscaped garden with a central fountain, stone benches, and a paved walkway leading to a green lawn.

19. 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, (60 reviews)
"Great stay"
United States
Carson M.
$380 nightly
The price is $418
Nov 2 - Nov 3
Total with taxes and fees
Jamul's Jewel: 10ACRES,Hilltop,Heated*Salt Pool,Spa*,City & Mtn.Views,B-Ball Court*,Grill,Horseshoes
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

Crowne Plaza San Diego - Mission Valley by IHG

Crowne Plaza San Diego - Mission Valley by IHG

10/10 Excellent
"The room was great spacious and clean the open layout was pleasant"
Victor 2-night trip
Posted less than an hour ago
Crowne Plaza San Diego - Mission Valley by IHG

Find out more about Winter Gardens

Everything you need to know about Winter Gardens vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Gardens vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Gardens vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winter Gardens in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $115 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Gardens rentals

At Expedia, we put the best Winter Gardens vacation 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 vacation.

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 vacation rentals in Winter Gardens?

Yes, we give you a choice of vacation rentals where you'll be just 14.3 mi (22.9 km) from San Diego Zoo, giving you a more secluded option if you want a quiet place to stay.

What are some of the best vacation home rentals in Winter Gardens?

Spacious 6 Bedroom Vacation Home with Waterslide & Heated Saltwater Pool: This vacation home rental near Winter Gardens is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Winter Gardens?

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

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 vacation rentals like in Winter Gardens?

Vacation rentals are privately owned accommodations you can book for several days or more in Winter Gardens. Vacation rentals offer extras like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.