Compare Winter Haven Vacation Rentals

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Winter Haven Rentals

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
7593 Gathering Drive, Kissimmee, FL
19.23 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 dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this luxury aparthotel include a lazy river, a children's pool, and a gym.
Pool
Hot Tub
Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

4 out of 5
Formosa Vly Pl, Kissimmee, FL
21.84 mi from city center
$451 nightly
The price is $501 total per night
$501 total
Aug 10 - Aug 11
Total includes taxes and fees
Guests staying at Formosa Valley Resort by UNE Homes enjoy features like an outdoor pool. There's free parking if you drive. A multilingual staff is on hand to help with tours or tickets, and offer sightseeing advice.
Pool
Kitchen
Encantada Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ

3 out of 5
3070-B Secret Lake Drive, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
22.63 mi from city center
$273 nightly
The price is $310 total per night
$310 total
Aug 12 - Aug 13
Total includes taxes and fees
At Encantada Resort Vacation Townhomes by IDILIQ, guests enjoy 2 outdoor pools, a children's pool, and a 24-hour gym. You can put free parking to good use if you drive. The front desk has multilingual staff that can help with luggage storage, tours or tickets, and securing valuables. Other amenities at this family-friendly aparthotel include 2 hot tubs, a 24-hour business center, and a meeting room.
Pool
Hot Tub
Summer Bay Orlando by Exploria Resorts

Summer Bay Orlando by Exploria Resorts

3.5 out of 5
17805 US Highway 192, Clermont, FL
Free Cancellation
Reserve now, pay when you stay
22.86 mi from city center
$150 nightly
The price is $167 total per night
$167 total
Aug 14 - Aug 15
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 concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this family-friendly condominium resort include a gym, 4 hot tubs, and outdoor tennis courts.
Pool
Hot Tub
Grand Lake Resort

Grand Lake Resort

3 out of 5
7770 W Irlo Bronson Memorial Hwy, Kissimmee, FL
23.37 mi from city center
Guests of Grand Lake Resort have access to an outdoor pool, a gym, and free WiFi in public areas. You can take advantage of free parking if you drive. A multilingual staff is on hand to assist with tours/tickets and luggage storage. Other amenities at this family-friendly aparthotel include a business center, a computer station, and a free grocery shopping service.
Pool
Kitchen
Lifetime of Vacations Resort

Lifetime of Vacations Resort

3 out of 5
7770 W Irlo Bronson Memorial Hwy, Kissimmee, FL
23.41 mi from city center
Lifetime of Vacations Resort features an outdoor pool, a gym, and a business center. RV, bus, and truck parking is available. Friendly staff can provide luggage storage, and also offer advice about sightseeing. Additional amenities include a computer station, laundry facilities, and a vending machine.
Pool
Kitchen
Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

4 out of 5
3151 Pantanal Lane, Kissimmee, FL
23.57 mi from city center
At Magic Village Yards, Trademark Collection by Wyndham, guests enjoy features like an outdoor pool, a gym, and free WiFi in public areas. If you plan to drive, free parking is available. The front desk has multilingual staff that can help with concierge services, luggage storage, and securing valuables. Additional amenities include a hot tub, a business center, and a computer station.
Pool
Hot Tub
The Berkley, Orlando

The Berkley, Orlando

4 out of 5
8545 W. Irlo Bronson Highway, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
23.44 mi from city center
$117 nightly
The price is $131 total per night
$131 total
Aug 11 - Aug 12
Total includes taxes and fees
At The Berkley, Orlando, guests enjoy 2 outdoor pools, a children's pool, and a gym. There's free parking and a free theme park shuttle. Front-desk staff can assist with concierge services and luggage storage. Other amenities at this family-friendly vacation home include free WiFi in public areas, a hot tub, and a business center.
Pool
Hot Tub
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4 out of 5
8000 Fins Up Circle, Kissimmee, FL
23.63 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 concierge services, access to locker space, and luggage storage. 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
Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ

4 out of 5
5780 Golden Hawk Way, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
24.79 mi from city center
$274 nightly
The price is $311 total per night
$311 total
Aug 27 - Aug 28
Total includes taxes and fees
Guests of Regal Oaks Resort Vacation Townhomes by IDILIQ have access to 2 outdoor pools, a free water park, and a gym. If you decide to drive, there's free parking. The front desk has multilingual staff that can help with luggage storage, tours or tickets, and securing valuables. Other amenities at this family-friendly condominium resort include free WiFi in public areas, a hot tub, and an outdoor tennis court.
Pool
Hot Tub
Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando

2.5 out of 5
2754 Florida Plaza Blvd, Kissimmee, FL
Free Cancellation
24.9 mi from city center
$132 nightly
The price is $150 total per night
$150 total
Aug 8 - Aug 9
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
Vacation Village at Parkway

Vacation Village at Parkway

3 out of 5
2975 Arabian Nights Blvd, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
24.87 mi from city center
$88 nightly
The price is $100 total per night
$100 total
Aug 12 - Aug 13
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 luggage storage and concierge services. Other amenities at this family-friendly condo building include 7 hot tubs, free WiFi in public areas, and a business center.
Pool
Hot Tub
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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 Haven Large Group Rentals

How to Book Vacation Rentals in Winter Haven



🏠 What is the best price for Winter Haven vacation rentals?

Winter Haven vacation rentals range in price, starting at $100 per night.


🏠 What types of vacation rentals in Winter Haven can I rent?

Orbitz offers a wide range of Winter Haven 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 Haven condo rentals.


🏠 Is it free to cancel my Winter Haven 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 Haven 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 Haven. 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 Haven?

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 Haven apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Winter Haven?

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 Haven package deals will get you even more savings.

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