What are the top rated Cottage Rentals in Winter Gardens?

There are a lot of options in Winter Gardens. If you plan on staying in the Winter Gardens area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Winter Gardens: <a href="/property/private-hilltop-estate-pool-spa-bar-arcade/HA-3213112728" class="class="static-page-link"">Private Hilltop Estate: Pool, Spa, Bar, Arcade</a> <a href="/property/luxe-3br-retreat-pool-spa-socal-haven/HA-3214074946" class="class="static-page-link"">Luxe 3BR Retreat Pool &amp; Spa, SoCal Haven</a> <a href="/property/lakeside-hilltop-retreat/HA-1217858167" class="class="static-page-link"">Lakeside Hilltop Retreat</a> <a href="/property/entire-private-home-with-3-bedrooms-2bathrooms-with-yard-parking-king-bed-hot-tub-available-now/BC-14892683" class="class="static-page-link"">Entire Private Home with 3 Bedrooms 2Bathrooms, with Yard, Parking, King Bed, Hot Tub, Available Now</a> <a href="/property/wheelchair-friendly-4bed-3bath-home-in-the-san-diego-suburbs/HA-3213834463" class="class="static-page-link"">Wheelchair friendly 4bed 3bath home in the San Diego Suburbs</a> <a href="/property/secluded-oasis-pickleball-jacuzzi-pool-views/HA-3213673743" class="class="static-page-link"">Secluded Oasis: Pickleball, Jacuzzi, Pool, &amp; Views</a> <a href="/property/luxury-panoramic-paradise/HA-3214705290" class="class="static-page-link"">Luxury-Panoramic Paradise</a> <a href="/property/deluxe-1-bedroom/HA-3214621362" class="class="static-page-link"">Deluxe 1 - Bedroom</a> <a href="/property/romantic-hillside-retreat-at-birdie-s-bungalow/HA-3213054487" class="class="static-page-link"">Romantic Hillside Retreat at Birdie’s Bungalow</a> <a href="/property/bird-of-paradise-retreat-with-stunning-mountain-views/BC-13271455" class="class="static-page-link"">Bird of Paradise Retreat with stunning mountain views</a>

How much does it cost to rent a cottage in Winter Gardens?

The average cost for a cottage rental in Winter Gardens is $1,004 per night. Cottageromance has a wide list of great cottages near Winter Gardens that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Winter Gardens that allow pets?

Yes, here are the top cottage rentals in Winter Gardens that allow you to bring your pet: Sleeps 40+ NEW Luxury Private Resort with Pool Golf Arcade Spa Playground Poker Villa Paradiso Tiny House Farm Stay with Outdoor Kitchen, Private Deck & Shared Pool Luxury Resort POOL/SPA/Golf/Grill/Games/Sleep 40+ Luxe 3BR Retreat Pool & Spa, SoCal Haven El Cajon Home with Wheelchair Access and Big Yard! Hampton Inn & Suites El Cajon San Diego Wheelchair friendly 4bed 3bath home in the San Diego Suburbs <a href="/all/usa/california/winter-gardens" class="class="static-page-link"">See all pet-friendly vacation rentals in Winter Gardens on Cottageromance</a>

Do you have any rental cottages in Winter Gardens that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Winter Gardens to find one that works for you.

Are there quality cottages in Winter Gardens that have indoor swimming pools?

As of 2026, the data from Cottageromance shows that there are Over 10 private swimming pools or cottages with indoor pools in the Winter Gardens area along with other great amenities.

Winter Gardens Cottage Rentals By Owner

Sleeps 40+ NEW Luxury Private Resort with Pool Golf Arcade Spa Playground Poker

From US $2,088

10.0 (14 Reviews)

Villa

Sleeps 40+ NEW Luxury Private Resort with Pool Golf Arcade Spa Playground Poker

Air Conditioner
Parking
Pet Friendly

Winter Gardens Cottage Rentals & Holiday Homes

Find the best cottages in Winter Gardens - We found 10 exact matches

When do you want to travel?