Compare Winter Haven Vacation Rentals

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Winter Haven Rentals

2-Story Slide & Disney Magic – The Ultimate Family Adventure Awaits!

2-Story Slide & Disney Magic – The Ultimate Family Adventure Awaits!

Davenport FL
17.56 mi from city center
At this vacation home, guests enjoy features like an outdoor pool, a gym, and a hot tub. Other amenities at this golf vacation home include an arcade/game room, laundry facilities, and barbecue grills.
Pool
Hot Tub
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
7593 Gathering Drive Kissimmee FL
19.27 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
Encore Resort

Encore Resort

4 out of 5
101 Lasso Drive Kissimmee FL
20.39 mi from city center
Guests staying at this vacation home enjoy an outdoor pool, express check-out, and laundry facilities. If you drive, put free parking to good use.
Pool
Kitchen
Villas At Regal Palms

Villas At Regal Palms

4 out of 5
2700 Sand Mine Road Consolidated Resorts Davenport FL
20.22 mi from city center
Villas At Regal Palms features an outdoor pool, a lazy river, and a gym. If you drive, put free parking to good use. The 24-hour front desk has multilingual staff ready to assist with concierge services and dry cleaning/laundry. Other amenities at this golf aparthotel include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
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
$291 nightly
The price is $331 total per night
$331 total
Jun 21 - Jun 22
Total with 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 securing valuables, luggage storage, and tours or tickets. Other amenities at this family-friendly aparthotel include 2 hot tubs, free WiFi in public areas, and a 24-hour business center.
Pool
Hot Tub
Grand Lake Resort

Grand Lake Resort

3 out of 5
7770 W Irlo Bronson Memorial Hwy Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
23.37 mi from city center
$81 nightly
The price is $91 total per night
$91 total
Jun 28 - Jun 29
Total with taxes and fees
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
The Berkley, Orlando

The Berkley, Orlando

4 out of 5
8545 W. Irlo Bronson Highway Kissimmee FL
23.35 mi from city center
$180 nightly
The price is $203 total per night
$203 total
Jun 22 - Jun 23
Total with 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 luggage storage and concierge services. 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 by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

4 out of 5
8000 Fins Up Circle Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
23.63 mi from city center
$395 nightly
The price is $449 total per night
$449 total
Jul 20 - Jul 21
Total with taxes and fees
Guests of Margaritaville Cottages Orlando by Rentyl with H2O Waterpark 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
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
24.78 mi from city center
$288 nightly
The price is $327 total per night
$327 total
Jun 21 - Jun 22
Total with 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 aparthotel 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
Jun 21 - Jun 22
Total with 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 Orlando, Celebration

Vacation Village Orlando, Celebration

3 out of 5
2975 Arabian Nights Blvd Kissimmee FL
Free Cancellation
Reserve now, pay when you stay
24.87 mi from city center
$99 nightly
The price is $112 total per night
$112 total
Jun 28 - Jun 29
Total with taxes and fees
Guests of Vacation Village Orlando, Celebration enjoy 7 outdoor pools, a children's pool, and a gym. You can take advantage of onsite parking for a fee, along 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 Suites

Barefoot Suites

3 out of 5
2750 Florida Plaza Blvd Kissimmee FL
24.91 mi from city center
$91 nightly
The price is $103 total per night
$103 total
Jul 13 - Jul 14
Total with taxes and fees
Guests staying at Barefoot Suites enjoy an outdoor pool, a children's pool, and free WiFi in public areas. If you drive, take advantage of free parking. The 24-hour front desk has multilingual staff ready to assist with luggage storage and securing valuables. Other amenities at this family-friendly aparthotel include a hot tub, a business center, and a computer station.
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 $91 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.