Winter Haven Vacation Rentals

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Vacation Rentals in Winter Haven

Aerial view
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3037)
"Great place to stay"
United States
Jose
The price is P5,376
P7,578 total
includes taxes & fees
Dec 1 - Dec 2
Vacation Village Orlando, Celebration
Interior
Margaritaville Cottages Orlando by Rentyl

Margaritaville Cottages Orlando by Rentyl

4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1707)
"Our favorite hotel!"
United States
Odanis
The price is P11,752
P25,159 total
includes taxes & fees
Nov 22 - Nov 23
Margaritaville Cottages Orlando by Rentyl
Lobby
The Berkley, Orlando

The Berkley, Orlando

4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (1975)
"This property meets ALL my needs and I'll continue to stay here when i visit Orlando. Always friendly staff when i arrive there! Looking forward to my next visit, next year."
United States
Julia
The price is P7,479
P9,085 total
includes taxes & fees
Nov 20 - Nov 21
The Berkley, Orlando
2 bars/lounges, poolside bar
Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
Kissimmee
8.4 out of 10, Very Good, (3006)
"Superb accommodation and an excellent location for the parks if you have hired a car. My only criticism was we had a huge cockroach in the house that we had to get rid of. "
United Kingdom
Jordan
The price is P7,045
P19,658 total
includes taxes & fees
Nov 30 - Dec 1
Regal Oaks Resort Vacation Townhomes by IDILIQ
Water park
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5.0 star property
Reunion
8.8 out of 10, Excellent, (1422)
"Was amazing beautiful and is an special place to go with kids , we love it !! "
United States
Yamila
Reunion Resort & Golf Club
Outdoor pool, pool umbrellas, sun loungers
Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
Kissimmee
9.2 out of 10, Wonderful, (1152)
"Easy check-in, clean room"
United States
THOMAS
Magic Village Yards, Trademark Collection by Wyndham
Exterior
Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando

2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (156)
"Condo has a friendly staff, clean and walking distance to Old Town. "
United States
BONNIE
The price is P7,168
P8,873 total
includes taxes & fees
Nov 17 - Nov 18
Barefoot'n Resort Kissimmee Orlando
Exterior
Magical Dreams

Magical Dreams

4.0 star property
Kissimmee
7.0 out of 10, Good, (4)
"This was one of the worst lodging experiences we’ve ever had. We booked through Hotels.com thinking this was a hotel or private suite. Instead, it turned out to be a single bedroom and bathroom inside a shared house in the Bella Vida subdivision. The house was not clean—dirty carpets, marked walls, and bugs. Parking was a major issue. The driveway was full, the street had “No Parking” signs, and no realistic alternative was provided. We parked our small Chevy Trax in the marked spot “E,” which...
United States
Sean
The price is P3,366
P7,842 total
includes taxes & fees
Nov 17 - Nov 18
Magical Dreams
2 outdoor pools, pool umbrellas, sun loungers
Encantada Resort Vacation Townhomes by IDILIQ

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
Kissimmee
8.6 out of 10, Excellent, (1398)
"Everything was great over all"
United States
Jesus
The price is P6,461
P18,996 total
includes taxes & fees
Dec 7 - Dec 8
Encantada Resort Vacation Townhomes by IDILIQ
Dock
Grand Lake Resort

Grand Lake Resort

3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (149)
"Very nice property staff are very nice "
United States
Dian
Grand Lake Resort
Dock
Barefoot Suites

Barefoot Suites

3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1786)
"Yes Espectacular, from the sixth floor I we saw Disneys fireworks ❤️❤️"
United States
Daniel
Barefoot Suites
Private pool
Formosa Valley Resort by UNE Homes

Formosa Valley Resort by UNE Homes

4.0 star property
Kissimmee
9.4 out of 10, Exceptional, (186)
"Brilliantly decorated and very spacious villa in a perfect location. "
United Kingdom
Bradley
The price is P8,770
P28,792 total
includes taxes & fees
Nov 17 - Nov 18
Formosa Valley Resort by UNE Homes
2 outdoor pools, open 8 AM to 10 PM, sun loungers
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 star property
Davenport
9.2 out of 10, Wonderful, (495)
"Everything was excellent! "
United States
Laura
The price is P6,791
P8,503 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Lake view
Lifetime of Vacations Resort

Lifetime of Vacations Resort

3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (149)
"The room was spacious and clean. Staff was kind and professional. Highly recommended!!"
United States
Kishi
Lifetime of Vacations Resort
Private kitchen
Summerville Vacation Homes by Columbia Management

Summerville Vacation Homes by Columbia Management

4.0 star property
Kissimmee
8.4 out of 10, Very Good, (152)
"Nice place ,plenty of room to relax,, hottub was also a great place to hang out after a long day of walking the parks"
United States
Kevin
Summerville Vacation Homes by Columbia Management
Exterior
Landing Townhomes Davenport

Landing Townhomes Davenport

4.0 star property
Davenport
8.8 out of 10, Excellent, (8)
"I appreciate everything that was provided. Everthing was great with the exception no access to gym after office hours and closed on Sunday. "
United States
ANGEL
Landing Townhomes Davenport
Sauna
Harmony Haven

Harmony Haven

2.5 star property
Kissimmee
The price is P2,953
P7,373 total
includes taxes & fees
Nov 17 - Nov 18
Harmony Haven
4 bedrooms, blackout drapes, iron/ironing board, free WiFi
Doppio Westside

Doppio Westside

4.0 star property
Davenport
9.4 out of 10, Exceptional, (23)
"My family loved our stay highly recommend for family vacation. I would stay here again in the future!"
United States
Myia
The price is P9,780
P25,175 total
includes taxes & fees
Nov 17 - Nov 18
Doppio Westside
2 outdoor pools
Champions Gate condos by UNE

Champions Gate condos by UNE

4.0 star property
Champions Gate
9.0 out of 10, Wonderful, (49)
"Very beautiful property."
United States
Alfred
The price is P7,654
P19,411 total
includes taxes & fees
Nov 18 - Nov 19
Champions Gate condos by UNE
Outdoor pool, a heated pool
Caribe Cove Resort

Caribe Cove Resort

3.5 star property
Kissimmee
8.8 out of 10, Excellent, (2259)
"The property was clean and quiet. "
United States
THEIRICK
Caribe Cove Resort
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.
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Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"We didn’t eat at the restaurant but really took in the atmosphere of the hotel. A big!!! Plus that the hotel had a restroom in the lobby."
Keshia 1-night trip
Posted 16 hours ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Haven

Search for holiday rentals in Winter Haven on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter Haven using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winter Haven!

Frequently asked questions

Can I find a vacation rental in Winter Haven?

Yes, there are vacation rentals in Winter Haven close to LEGOLAND® Florida, or you can choose a more secluded option if you'd like a relaxing place to stay. Visitors to Winter Haven speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave time to check out the gardens and entertainment venues during your visit.

What's the top vacation rental that Winter Haven has to offer?

The Berkley, Orlando: This vacation home rental outside of Winter Haven offers a furnished patio, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave, and a coffee maker. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Winter Haven?

Choose from 130 Expedia vacation rentals in Winter Haven for a memorable vacation.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Peppa Pig Theme Park Florida, whereas The Circle B Bar Reserve and Inman Park are a couple of great spots to enjoy the outdoors. Theatre Winter Haven and Chain of Lakes Park are other places to visit while you're in town.

What are vacation rentals like in Winter Haven?

Vacation rentals are private properties you can book for a few days or a quick weekend in Winter Haven. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.