Compare Winter Garden Vacation Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Winter Garden Rentals
Summer Bay Orlando by Exploria Resorts
17805 US Highway 192, Clermont, FL
Free Cancellation
Reserve now, pay when you stay
15.73 mi from city center
$158 nightly
The price is $176 total per night
$176 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests of Summer Bay Orlando by Exploria Resorts enjoy 5 outdoor pools, karaoke, and a children's pool. You can take advantage of free parking, along with a free area shuttle. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, securing valuables, and luggage storage. Other amenities at this family-friendly condominium resort include a gym, 4 hot tubs, and outdoor tennis courts.
Pool
Hot Tub
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
8000 Fins Up Circle, Kissimmee, FL
15.18 mi from city center
Guests of Margaritaville Cottages Orlando with H2O Waterpark by Rentyl have access to a full-service spa, a free water park, and an outdoor pool. A stay here includes free parking. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, access to locker space, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Other amenities at this spa aparthotel include a lazy river, a gym, and a sauna.
Pool
Hot Tub
Vacation Village at Parkway
2975 Arabian Nights Blvd, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
16.19 mi from city center
$100 nightly
The price is $114 total per night
$114 total
Jul 27 - Jul 28
Total includes taxes and fees
Guests of Vacation Village at Parkway enjoy 7 outdoor pools, a children's pool, and a gym. Transportation is made easy with an area shuttle. The 24-hour front desk has staff standing by to help with concierge services and luggage storage. Other amenities at this family-friendly condo building include 7 hot tubs, free WiFi in public areas, and a business center.
Pool
Hot Tub
Barefoot'n Resort Kissimmee Orlando
2754 Florida Plaza Blvd, Kissimmee, FL
16.85 mi from city center
$120 nightly
The price is $136 total per night
$136 total
Jul 28 - Jul 29
Total includes taxes and fees
At Barefoot'n Resort Kissimmee Orlando, guests enjoy an outdoor pool, a children's pool, and free WiFi in public areas. Free parking is available if you drive. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Additional amenities include a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
Reunion Resort & Golf Club
7593 Gathering Drive, Kissimmee, FL
20.41 mi from city center
Reunion Resort & Golf Club features a golf course, 11 outdoor pools, and a free water park. Self parking is available for USD 20 per day. Multilingual staff at the 24-hour front desk can assist with securing valuables, dry cleaning/laundry, and luggage storage. Other amenities at this luxury aparthotel include a lazy river, a children's pool, and a gym.
Pool
Hot Tub
Floridays Resort Orlando
12562 International Drive, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
13.76 mi from city center
$183 nightly
The price is $206 total per night
$206 total
Aug 17 - Aug 18
Total includes taxes and fees
Guests of Floridays Resort Orlando have access to 2 outdoor pools, a gym, and conference space. You can take advantage of free parking, along with an area shuttle. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, securing valuables, and dry cleaning/laundry. Other amenities at this family-friendly condominium resort include a 24-hour business center, a computer station, and an arcade/game room.
Pool
Kitchen
Lake Buena Vista Resort Village & Spa
8113 Resort Village Drive, Orlando, FL
15.9 mi from city center
Guests of Lake Buena Vista Resort Village & Spa have access to a full-service spa, 2 outdoor pools, and a children's pool. There's free parking and a free theme park shuttle. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and luggage storage. Other amenities at this spa condominium resort include a 24-hour gym, 3 hot tubs, and a steam room.
Pool
Hot Tub
Club Wyndham Cypress Palms
17.15 mi from city center
Guests staying at Club Wyndham Cypress Palms enjoy access to 2 outdoor pools, a 24-hour gym, and 2 hot tubs. If you drive, put free parking to good use. The front desk is staffed 24/7 to help with concierge services, luggage storage, and securing valuables. Additional amenities include free WiFi in public areas, a business center, and an arcade/game room.
Pool
Hot Tub
The Point by Edge
7389 Universal Boulevard, Orlando, FL
10.63 mi from city center
$71 nightly
The price is $80 total per night
$80 total
Aug 17 - Aug 18
Total includes taxes and fees
Guests of The Point by Edge have access to an outdoor pool, a gym, and free WiFi in public areas. Front-desk staff can help with concierge services, and provide local restaurant recommendations. This aparthotel also has a terrace.
Pool
Free WiFi
The Point Hotel & Suites
7389 Universal Blvd, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
10.66 mi from city center
$99 nightly
The price is $110 total per night
$110 total
Jul 28 - Jul 29
Total includes taxes and fees
Guests staying at The Point Hotel & Suites enjoy an outdoor pool, a gym, and free WiFi in public areas. If you drive, take advantage of free parking. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include a hot tub, a computer station, and express check-out.
Pool
Hot Tub
The View Studio Suites and Event Venue
9309 S Orange Blossom Trail, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
14.7 mi from city center
$90 nightly
The price is $102 total per night
$102 total
Jul 27 - Jul 28
Total includes taxes and fees
Guests staying at The View Studio Suites and Event Venue enjoy a 24-hour gym, free WiFi in public areas, and a picnic area. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready.
Breakfast included
Pet friendly
Florida Hotel & Conference Center in the Florida Mall
1500 Sand Lake Road, Orlando, FL
Free Cancellation
Reserve now, pay when you stay
14.25 mi from city center
$197 nightly
The price is $221 total per night
$221 total
Aug 9 - Aug 10
Total includes taxes and fees
At Florida Hotel & Conference Center in the Florida Mall, guests enjoy an outdoor pool, a gym, and free WiFi in public areas. There's RV, bus, and truck parking and a free theme park shuttle. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. Other amenities at this family-friendly aparthotel include a hot tub, a conference center, and a 24-hour business center.
Pool
Hot Tub
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.
Winter Garden Large Group Rentals
The Berkley, Orlando
8545 W. Irlo Bronson Highway, Kissimmee, FL
$117 nightly
The price is $131 total per night from Jul 28 to Jul 29
$131 total
Jul 28 - Jul 29
Total includes taxes and fees
9.4/10 Exceptional! (1,849 reviews)
Marriott's Sabal Palms
8805 World Center Dr, Orlando, FL
$199 nightly
The price is $224 total per night from Aug 14 to Aug 15
$224 total
Aug 14 - Aug 15
Total includes taxes and fees
9.4/10 Exceptional! (194 reviews)
Formosa Valley Resort by UNE Homes
Formosa Vly Pl, Kissimmee, FL
$481 nightly
The price is $535 total per night from Jul 29 to Jul 30
$535 total
Jul 29 - Jul 30
Total includes taxes and fees
9.4/10 Exceptional! (159 reviews)
Close to Disney! Private Pool-Spa! Game Room!
Kissimmee
9.4/10 Exceptional! (6 reviews)
Marriott's Imperial Palm Villas
8404 Vacation Way, Orlando, FL
$239 nightly
The price is $269 total per night from Aug 14 to Aug 15
$269 total
Aug 14 - Aug 15
Total includes taxes and fees
9/10 Wonderful! (57 reviews)
Encore Resort
101 Lasso Drive, Kissimmee, FL
6.4/10 (117 reviews)
How to Book Vacation Rentals in Winter Garden
🏠 What is the best price for Winter Garden vacation rentals?
Winter Garden vacation rentals range in price, starting at $80 per night.
🏠 What types of vacation rentals in Winter Garden can I rent?
Orbitz offers a wide range of Winter Garden rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Winter Garden condo rentals.
🏠 Is it free to cancel my Winter Garden vacation rental with Orbitz?
Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.
🏠 How do I find the best deals to rent a Winter Garden vacation rental with Orbitz?
There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Winter Garden. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.
🏠 How can I cancel my vacation rental booking through Orbitz?
Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.
🏠 What are the advantages of booking a vacation rental in Winter Garden?
Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Winter Garden apartments and enjoy an extended stay.
🏠 Why should I book my vacation rental with Orbitz in Winter Garden?
Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Winter Garden package deals will get you even more savings.
More Places To Stay in Winter Garden
Recommended Vacation Rental Locations
Book on Expedia
Top Trending
Hotels
- Daytona Beach Hotel Deals
- Naples Hotel Deals
- St. Augustine Beach Resorts & Hotels
- Daytona Beach Cheap Hotels
- Destin Beach Resorts & Hotels
- Sarasota Beach Resorts & Hotels
- Cocoa Beach Hotel Deals
- Fort Myers Hotel Deals
- Sarasota Hotel Deals
- Pensacola Cheap Hotels
- Fort Walton Beach Hotel Deals
- Key West Hotel Deals
- Fort Myers Beach Hotel Deals
- St. Augustine Hotel Deals
- Panama City Beach Hotel Deals
- Pensacola Beach Resorts & Hotels
- Key West Cheap Hotels
- Key West All Inclusive Resorts & Hotels
- Naples Oceanfront Hotels
Flights