Winter Gardens holiday rentals

We found 639 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Winter Gardens that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include a garden and pool. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Winter Gardens

Showing deals for:25 Dec - 1 Jan

Private kitchen
Pool
Living area
Dining
Exceptional
(25 reviews)

Luxury Agua de Sol - Views/Pool/Spa/Sauna/Gym/EV In the heart of San Diego

San Diego

8% off
AU$14,894
for 7 nights, 1 home
AU$2,128 per night
includes taxes & fees
Luxury Agua de Sol - Views/Pool/Spa/Sauna/Gym/EV In the heart of San Diego
Games room
Pool
Pool
Interior
Exceptional
(6 reviews)

Elegant Pool Villa In Mount Helix, close to DT!

La Mesa

12% off
AU$9,518
for 7 nights, 1 home
AU$1,360 per night
includes taxes & fees
Elegant Pool Villa In Mount Helix, close to DT!
Interior
Private kitchen
Interior
Interior
Exceptional
(8 reviews)

New Basement Apartment

La Mesa

16% off
AU$1,518
for 7 nights, 1 apartment
AU$217 per night
includes taxes & fees
New Basement Apartment
Private kitchen
Outdoor dining
Private kitchen
Room
Exceptional
(8 reviews)

Serenity - Amazing Views & Modern Charm, 1 bedrm, 1 bath, 2 beds, kitchen, deck

La Mesa

12% off
AU$2,625
for 7 nights, 1 apartment
AU$375 per night
includes taxes & fees
Serenity - Amazing Views & Modern Charm, 1 bedrm, 1 bath, 2 beds, kitchen, deck
Private kitchen
Living area
Private kitchen
Dining
Exceptional
(8 reviews)

Family Hilltop luxe retreat with breathtaking view

La Mesa

9% off
AU$4,734
for 7 nights, 1 home
AU$676 per night
includes taxes & fees
Family Hilltop luxe retreat with breathtaking view
Dining
Pool
Interior
Outdoor dining
Very good
(5 reviews)

Charming Hilltop Home · Private Pool · Arcade · Close to Downtown La Mesa

La Mesa

9% off
AU$5,593
for 7 nights, 1 home
AU$799 per night
includes taxes & fees
Charming Hilltop Home · Private Pool · Arcade · Close to Downtown La Mesa
Room
Private kitchen
Exterior detail
Private kitchen
Exceptional
(16 reviews)

Lake Murray 3BR Retreat with AC and Skylight

San Diego

9% off
AU$4,939
for 7 nights, 1 apartment
AU$706 per night
includes taxes & fees
Lake Murray 3BR Retreat with AC and Skylight

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Winter Gardens getaway

Learn about the unique charm of Winter Gardens with a stay in a holiday home rental. This city has something for everyone. San Diego Zoo and Petco Park are just a couple of the must-see attractions in the area. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Winter Gardens

Do you want to discover attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that makes Winter Gardens a fun place to get away to. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • San Diego Zoo (14.3 mi / 22.9 km)
  • Singing Hills Country Club - Willow Glen Course (4.3 mi / 6.9 km)
  • Carlton Oaks Country Club (4.5 mi / 7.2 km)
  • Steele Canyon Golf Club (6.5 mi / 10.5 km)
  • Barona Speedway (11.9 mi / 19.2 km)
  • Potato Chip Rock (12.5 mi / 20.1 km)

Exploring the natural landscape of Winter Gardens

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Winter Gardens is a great place to spend some time outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Balboa Park (14.1 mi / 22.6 km)
  • Sportsplex USA Santee (3.1 mi / 4.9 km)
  • Lake Jennings (3.2 mi / 5.2 km)
  • Santee Lakes (4.6 mi / 7.4 km)
  • Mission Trails Regional Park (7.2 mi / 11.6 km)
  • Old Poway Park (11.3 mi / 18.3 km)

How to get to and around Winter Gardens

The nearest airport is in San Diego, CA (SEE-Gillespie Field), located 2.4 mi (3.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into San Diego, CA (MYF-Montgomery Field), which is 12.2 mi (19.6 km) away.

Frequently asked questions

What is the best area to stay in Winter Gardens when booking a holiday rental?
When considering a holiday rental in Winter Gardens, California, a popular area to stay is the neighbourhood surrounding the historic downtown area. This vibrant locale offers a delightful blend of charm and convenience, making it an ideal base for exploring the region. Visitors will find a variety of properties available, ranging from quaint cottages to more spacious family homes, suiting different tastes and budgets.In downtown Winter Gardens, you'll be close to some of the top attractions, including the captivating Water Conservation Garden, which showcases beautiful native plants and sustainable landscaping practices. Another highlight is the nearby historical site of the Olde Towne Theatre, a charming venue that often hosts community events and performances, providing insight into the local culture.Staying in this area not only places you within walking distance of local shops and eateries but also offers easy access to scenic parks and outdoor activities that enhance your holiday experience.
What are the top attractions in Winter Gardens?
In Winter Gardens, California, visitors can explore several attractions that highlight both natural beauty and local charm. The nearby Cuyamaca Rancho State Park offers stunning hiking trails and scenic vistas, ideal for outdoor enthusiasts. The park is known for its diverse ecosystems, including oak woodlands and meadows, making it a great spot for picnicking and wildlife viewing.The area is also close to the historic town of Julian, famous for its apple pies and quaint shops, providing a delightful day trip experience. Additionally, the nearby Lake Cuyamaca is superb for fishing, boating, and enjoying a peaceful day by the water, making it a favourite among locals and tourists alike.
Are all fees included in the Winter Gardens holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winter Gardens holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winter Gardens with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winter Gardens holiday homes?
You can find great discounts on holiday homes in Winter Gardens on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winter Gardens holiday home booking on Stayz?
To find Winter Gardens holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winter Gardens?
A long-stay holiday home in Winter Gardens is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winter Gardens holiday home?
Book your Winter Gardens holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winter Gardens?
Prices for holiday homes in Winter Gardens vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winter Gardens to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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