Vacation rentals in Winter Haven

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Top vacation rentals in Winter Haven

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
$123 nightly
The price is $140 total per night
$140 total
Nov 20 - Nov 21
Total with taxes and fees
7 outdoor pools, 7 hot tubs, and a gym are all featured at this smoke-free condo. Bring the family and enjoy the children's pool, playground, and arcade/game room. WiFi in public areas is free.
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
Free Cancellation
Reserve now, pay when you stay
23.63 mi from city center
$355 nightly
The price is $403 total per night
$403 total
Nov 10 - Nov 11
Total with taxes and fees
This smoke-free aparthotel features free water park access, a full-service spa, and a restaurant. Bring the family and enjoy the lazy river, waterslide, and arcade/game room. Enjoy the outdoor pool and perks like free self parking and free WiFi.
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
$132 nightly
The price is $148 total per night
$148 total
Nov 11 - Nov 12
Total with taxes and fees
2 outdoor pools, a hot tub, and a gym are all featured at this smoke-free vacation home. There's fun for all ages with a children's pool and a theme park shuttle, and barbecue grills are available on site. Guests will appreciate free perks like free self parking and WiFi in public areas.
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
$288 nightly
The price is $327 total per night
$327 total
Nov 10 - Nov 11
Total with taxes and fees
Free water park access, 2 restaurants, and 2 outdoor pools are all featured at this Mediterranean condo resort. Bring the family and enjoy the waterslide, arcade/game room, and kid-friendly dining. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
7593 Gathering Drive, Kissimmee, FL
19.23 mi from city center
Get rates
This luxury aparthotel features a golf course, free water park access, and 7 restaurants. Bring the family and enjoy the lazy river, mini golf, and kid-friendly dining. Relax with a drink at one of the 2 poolside bars and enjoy the 11 outdoor pools and gym.
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
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This aparthotel features an outdoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
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
$292 nightly
The price is $331 total per night
$331 total
Nov 16 - Nov 17
Total with taxes and fees
2 outdoor pools, 2 hot tubs, and a 24-hour gym are all featured at this smoke-free aparthotel. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.
Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando

2.5 out of 5
2754 Florida Plaza Blvd, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
24.9 mi from city center
$83 nightly
The price is $95 total per night
$95 total
Nov 16 - Nov 17
Total with taxes and fees
This aparthotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, laundry facilities, and barbecue grills are also on offer.
Magical Dreams

Magical Dreams

4 out of 5
231 Marcello Blvd, Kissimmee, FL
25.14 mi from city center
$116 nightly
The price is $132 total per night
$132 total
Nov 10 - Nov 11
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A communal living room and a virtual front desk are also provided.
Barefoot Suites

Barefoot Suites

3 out of 5
2750 Florida Plaza Blvd, Kissimmee, FL
24.91 mi from city center
$93 nightly
The price is $106 total per night
$106 total
Nov 17 - Nov 18
Total with taxes and fees
This aparthotel features an outdoor pool and a hot tub. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Guests will appreciate free perks like free self parking and WiFi in public areas.
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 out of 5
100 Orlando Breeze Circle, Davenport, FL
Free Cancellation
22.28 mi from city center
$121 nightly
The price is $135 total per night
$135 total
Nov 9 - Nov 10
Total with taxes and fees
2 outdoor pools, a hot tub, and a gym are all featured at this traditional aparthotel. Bring the family and enjoy the mini golf, children's pool, and playground. Guests will appreciate free perks like free self parking and WiFi in public areas.
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
$456 nightly
The price is $507 total per night
$507 total
Nov 9 - Nov 10
Total with taxes and fees
An outdoor pool is featured at this vacation home, along with concierge services. Take advantage of the free self parking.
Grand Lake Resort

Grand Lake Resort

3 out of 5
7770 W Irlo Bronson Memorial Hwy, Kissimmee, FL
23.37 mi from city center
Get rates
This aparthotel features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Guests will appreciate free perks like free self parking and WiFi in public areas.
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
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This condo features an outdoor pool and a gym. A business center, a garden, and a picnic area are also on offer.
Summerville Vacation Homes by Columbia Management

Summerville Vacation Homes by Columbia Management

4 out of 5
2621 Sunrise Shores Drive, Kissimmee, FL
22.57 mi from city center
Get rates
This vacation home features an outdoor pool and a gym. Bring the family and enjoy the free kid's club, playground, and arcade/game room. Enjoy the hot tub and perks like free self parking and free WiFi.
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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.

The Best Way to Find your Vacation Rentals in Winter Haven

How cheap can a vacation rental in Winter Haven be?

You can find vacation rentals in Winter Haven for as low as $95 per night.

How do you look for the best vacation rental deals in Winter Haven with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout Winter Haven so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in Winter Haven can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in Winter Haven?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our Winter Haven vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in Winter Haven?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, Winter Haven vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in Winter Haven?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom Winter Haven vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.