Winter Haven Holiday Rentals

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Holiday Rentals in Winter Haven

Summer Bay Orlando by Exploria Resorts
5 outdoor pools

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5041)
"Great place to stay! Quiet and peaceful with lots of natural wildlife and plenty to do on the property. Will definitely be staying here again!"
The price is HK$944
HK$1,307 total
includes taxes & fees
2 Jan - 3 Jan 2025
Summer Bay Orlando by Exploria Resorts
Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1110)
"Great option for groups or families!"
Margaritaville Resort Orlando Cottages by Rentyl
Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1401)
"El hotel está en un lugar muy bueno bien cerca de los parques , el hotel está muy limpio con muchas condiciones muy limpio y un muy buen precio "
Vacation Village at Parkway
Reunion Resort & Golf Club
11 outdoor pools, open 8:00 AM to 11:00 PM, pool umbrellas

Reunion Resort & Golf Club

5.0 star property
8.6 out of 10, Excellent, (1193)
"Great stay!"
The price is HK$2,305
HK$2,985 total
includes taxes & fees
26 Dec - 27 Dec
Reunion Resort & Golf Club
The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1615)
"Very polite and clean"
The Berkley, Orlando
Regal Oaks Resort Vacation Townhomes by IDILIQ
2 outdoor pools, open 8:00 AM to 9:00 PM, pool cabanas (surcharge)

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very good, (2811)
"Had a great time "
The price is HK$880
HK$2,534 total
includes taxes & fees
19 Dec - 20 Dec
Regal Oaks Resort Vacation Townhomes by IDILIQ
Magic Village Yards, Trademark Collection by Wyndham
Outdoor pool, pool umbrellas, pool loungers

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1105)
"Best option "
Magic Village Yards, Trademark Collection by Wyndham
Bahama Bay Resort
Property grounds

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2045)
"Loved everything this property had will be booking again soon. "
Bahama Bay Resort
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, pool loungers

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1315)
"We loved the location and the community amenities. House was nice, clean and exactly what we needed. "
The price is HK$1,243
HK$2,534 total
includes taxes & fees
19 Dec - 20 Dec
Encantada Resort Vacation Townhomes by IDILIQ
Lifetime of Vacations Resort
Lake

Lifetime of Vacations Resort

3.0 star property
9.2 out of 10, Wonderful, (112)
"I loved the charming feel of the property. The rooms were very spacious and clean. The property was very well maintained and the staff was terrific "
The price is HK$818
HK$1,061 total
includes taxes & fees
12 Jan - 13 Jan 2025
Lifetime of Vacations Resort
Villas At Regal Palms
Outdoor pool, pool loungers

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very good, (512)
"Pool area was well kept and the restaurant staff were great. "
Villas At Regal Palms
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
Fridge, microwave, oven, stovetop

Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*

9.6 out of 10, Exceptional, (29)
"House was clean the pool was warm even though the weather was not. "
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
TV

Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!

9.2 out of 10, Wonderful, (23)
"Great stay with friends"
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
Grand Lake Resort
Outdoor pool, pool umbrellas, pool loungers

Grand Lake Resort

3.0 star property
9.0 out of 10, Wonderful, (101)
"The people at the property were great to deal with our whole stay. The grounds were nice and well maintained. Central to a lot of things we did while we visited. We are actually planning a 2 week stay in July. Love the property. Pool is nice. Lake is beautiful. "
The price is HK$1,224
HK$1,535 total
includes taxes & fees
12 Jan - 13 Jan 2025
Grand Lake Resort
Caribe Cove Resort
Outdoor pool

Caribe Cove Resort

3.5 star property
8.8 out of 10, Excellent, (2241)
"Condo is spacious, beds aren’t comfortable but for the price it’s understandable. If they could change the mattress would be amazing! Pool area is really nice. "
Caribe Cove Resort
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
Outdoor pool

Family house / 4 BD-2Baths (August promotion!! low rates for this month)

8.8 out of 10, Excellent, (23)
"As Milton barreled down on us we felt safe and comfortable . The owner checked in on us and made sure everything was ok. Thank you for making a stressful event better. Donna "
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME
A heated pool

MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME

MISSION TO MARS EXTREME PRIVATE ATTRACTION VACATION HOME
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!
Fridge, microwave, oven, stovetop

THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!

9.0 out of 10, Wonderful, (99)
"could have been cleaned better. plus closet door fell off in one room when trying to open. dangerous. glad it was me opening it and not my 3 year old granddaughter."
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (132)
"My family and I really enjoyed our stay. Would definitely stay!"
Formosa Valley Resort by UNE Homes
Luxury 4 bedroom 3 bath pool Home 283
A heated pool

Luxury 4 bedroom 3 bath pool Home 283

9.2 out of 10, Wonderful, (22)
"Great communication with host."
Luxury 4 bedroom 3 bath pool Home 283
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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Other types of properties in Winter Haven you may be interested in

Holiday Inn Winter Haven, an IHG Hotel
Bar (on property)

Holiday Inn Winter Haven, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Very nice stay and wonderful staff. Only complaint was a very slow elevator. One of the elevators was not working properly. "
The price is HK$932
HK$1,044 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Inn Winter Haven, an IHG Hotel
Best Western Plus Winter Haven Inn & Suites 
Desk, laptop workspace, blackout curtains, iron/ironing board

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
9.4 out of 10, Exceptional, (633)
"The front desk was so helpful and courteous the entire time very supportive. I would highly recommend."
The price is HK$1,063
HK$1,190 total
includes taxes & fees
23 Dec - 24 Dec
Best Western Plus Winter Haven Inn & Suites 
Howard Johnson by Wyndham Winter Haven FL
Blackout curtains, iron/ironing board, free cots/infant beds

Howard Johnson by Wyndham Winter Haven FL

2.0 star property
7.0 out of 10, Good, (1003)
"Nice"
The price is HK$793
HK$888 total
includes taxes & fees
29 Dec - 30 Dec
Howard Johnson by Wyndham Winter Haven FL
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.

Frequently asked questions

Can I find a holiday rental in Winter Haven?

Yes, there are holiday rentals in Winter Haven close to LEGOLAND® Florida, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Winter Haven has to offer?

The Berkley, Orlando: This holiday home rental outside of Winter Haven offers a furnished patio, a terrace and a BBQ 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 holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Winter Haven?

Choose from 128 Expedia holiday rentals in Winter Haven for a memorable holiday.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Indigo's Family Fun Center, 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 holiday rentals like in Winter Haven?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Haven. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.