Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

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, (3012)
"Nice place "
United States
Shadea
The price is ￥13,966
￥19,687 total
includes taxes & fees
Nov 23 - Nov 24
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, (1690)
"Having your private pool-spa was excellent and the rest of the grounds were excellent too, the pool with the hotel was my best pool ever.."
United States
Mary
The price is ￥27,462
￥61,878 total
includes taxes & fees
Nov 10 - Nov 11
Margaritaville Cottages Orlando by Rentyl
Lobby
The Berkley, Orlando

The Berkley, Orlando

4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (1968)
"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 ￥18,662
￥22,736 total
includes taxes & fees
Nov 11 - Nov 12
The Berkley, Orlando
View from property
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, (2999)
"Loved the location of the property and that the property was gated"
United States
Darlene
The price is ￥16,378
￥48,889 total
includes taxes & fees
Nov 10 - Nov 11
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, (1421)
"Was amazing beautiful and is an special place to go with kids , we love it !! "
United States
Yamila
The price is ￥32,111
￥43,718 total
includes taxes & fees
Dec 9 - Dec 10
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, (1149)
"Condo was decent, could have had a few more supplies in the unit. Half rolls of TP is pretty sh*tty... literally."
Canada
Aaron
Magic Village Yards, Trademark Collection by Wyndham
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, (1397)
"2nd time staying here safe to say this is our second home "
United States
Melanie
The price is ￥16,785
￥49,350 total
includes taxes & fees
Nov 16 - Nov 17
Encantada Resort Vacation Townhomes by IDILIQ
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 ￥12,995
￥16,658 total
includes taxes & fees
Nov 26 - Nov 27
Barefoot'n Resort Kissimmee Orlando
Outdoor pool
Magical Dreams

Magical Dreams

4.0 star property
Kissimmee
10.0 out of 10, Exceptional, (2)
"Parking can be an issue but as long as you communicate with the others, you’ll be alright. "
United States
Shana
The price is ￥8,501
￥20,066 total
includes taxes & fees
Nov 25 - Nov 26
Magical Dreams
Dock
Barefoot Suites

Barefoot Suites

3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1783)
"Wonderful !!"
United States
carol
Barefoot Suites
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, (494)
"Everything was excellent! "
United States
Laura
The price is ￥16,431
￥20,730 total
includes taxes & fees
Nov 9 - Nov 10
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
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, (185)
"Overall a clean house, one of the best properties I’ve stayed in. "
United States
Cristian
The price is ￥22,783
￥74,799 total
includes taxes & fees
Nov 9 - Nov 10
Formosa Valley Resort by UNE Homes
Dock
Grand Lake Resort

Grand Lake Resort

3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (147)
"Very nice property staff are very nice "
United States
Dian
Grand Lake Resort
Lake view
Lifetime of Vacations Resort

Lifetime of Vacations Resort

3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (148)
"Quiet place "
United States
Iliana
Lifetime of Vacations Resort
Captiva-06 (SMV104) | Private kitchen | Fridge, microwave, oven, stovetop
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
8.6 out of 10, Excellent, (7)
"Entrega una hora más tarde de lo acordado y al llamar al servicio al cliente una “Dama” si se le puede llamar así muy mal educada y poco cordial "
Mexico
Duamel González
Landing Townhomes Davenport
Outdoor pool, a heated pool
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool

Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool

Kissimmee
9.6 out of 10, Exceptional, (48)
"Very nice property. The kids really enjoyed the themed rooms."
United States
Ahmed E.
Glam Villa Near the Parks w Gamer & Princess BRs, Huge Theater, Arcade, Spa Pool
Outdoor pool
VedaHive Luxury Villa

VedaHive Luxury Villa

3.0 star property
Solterra Resort
5.6 out of 10, (5)
"The entire house was nice but what I didn’t like is that it didn’t say anything about a shared bathroom only says shared kitchen. The only thing private you have is the room. The parking is not reserved as they say, it’s a first come first serve basis and on the weekends when it’s busy your guaranteed to have no choice but to wait til midnight when they start to tow cars that didn’t have permits. We actually had a long trip and came back at 9:30pm but had to sit outside and wait til midnight....
United States
Maribel
The price is ￥9,177
￥29,151 total
includes taxes & fees
Nov 15 - Nov 16
VedaHive Luxury Villa
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 ￥17,145
￥47,320 total
includes taxes & fees
Nov 9 - Nov 10
Champions Gate condos by UNE
House (6 Bedrooms) | Interior
Encore Swanky

Encore Swanky

3.0 star property
Kissimmee
Encore Swanky
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

Delta Hotels by Marriott Orlando Celebration

Delta Hotels by Marriott Orlando Celebration

10/10 Excellent
"Good"
Darian 3-night trip
Posted 2 days ago
Delta Hotels by Marriott Orlando Celebration

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:

  • View our selection of featured holiday rentals in Winter Haven
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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 132 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 Rotary 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.