Winter Haven Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Winter Haven holiday rentals

Interior

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is S$553
includes taxes & fees
21 Feb - 22 Feb
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Living area

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"House was great, perfect central location. Very quiet neighborhood nice farm outside peaceful back yard seating area. "
United States
Wade
The price is S$339
includes taxes & fees
1 Mar - 2 Mar
BlockHaven near Legoland & Disney
Outdoor pool, pool umbrellas, pool loungers

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
The price is S$106
includes taxes & fees
18 Feb - 19 Feb
Lake Ida Beach Resort
Exterior

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.4 out of 10, Good, (1,010 reviews)
"Staff was very helpful, location was what we needed and rooms and pool were outstanding "
United States
Chester Joseph
The price is S$130
includes taxes & fees
24 Feb - 25 Feb
voco Kissimmee Orlando by IHG
Marina

Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (198 reviews)
"Nice rooms helpful staff would go again for sure"
United States
David
Camp Mack Lodge, Marina & RV Resort
2 outdoor pools

Oasis Private Ensuite Room Shared Home

Oasis Private Ensuite Room Shared Home
3.5 star property
Kissimmee
The price is S$180
includes taxes & fees
27 Feb - 28 Feb
Oasis Private Ensuite Room Shared Home
Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,376 reviews)
"Yes .. very clean rooms and hotel chef was great"
United States
Alicia
The price is S$153
includes taxes & fees
8 Mar - 9 Mar
Vacation Village Orlando, Celebration
Pool

Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse

Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse
3.5 star property
Kissimmee
Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse
Full-sized fridge, microwave, oven, stovetop

Leisure Lounge

Leisure Lounge
3.5 star property
Solterra Resort
8.0 out of 10, Very good, (18 reviews)
"The room was so nice! Very clean and in tact."
United States
Amber Carchelle
The price is S$146
includes taxes & fees
26 Feb - 27 Feb
Leisure Lounge
Exterior

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (203 reviews)
"Great place. Great location. "
United States
Andrew
The price is S$160
includes taxes & fees
22 Feb - 23 Feb
Barefoot'n Resort Kissimmee Orlando
5 bedrooms

Mickey s Villa - Child-friendly Game Room Pool Spa

Mickey s Villa - Child-friendly Game Room Pool Spa
2.0 star property
Kissimmee
The price is S$670
includes taxes & fees
23 Feb - 24 Feb
Mickey s Villa - Child-friendly Game Room Pool Spa
Outdoor pool, pool umbrellas, pool loungers

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,828 reviews)
"Great place. To stay "
United States
THOMAS
Barefoot Suites
Outdoor pool

Magical Dreams

Magical Dreams
4.0 star property
Kissimmee
5.4 out of 10, (17 reviews)
"Overall was a good stay . "
United States
Sorina
The price is S$184
includes taxes & fees
3 Mar - 4 Mar
Magical Dreams
Lobby

Elita Inn

Elita Inn
3.0 star property
Dundee
7.6 out of 10, Good, (25 reviews)
"Very nice accommadations..friendly staff"
United States
lance
The price is S$112
includes taxes & fees
18 Mar - 19 Mar
Elita Inn
Property amenity

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, (529 reviews)
"It was lovely! We would stay here again for sure! "
United States
Hilary
The price is S$201
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Interior entrance

Jade Manor

Jade Manor
2.5 star property
Solterra Resort
8.8 out of 10, Excellent, (3 reviews)
"Amazing "
United States
Nilda
The price is S$170
includes taxes & fees
2 Mar - 3 Mar
Jade Manor
Exterior

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, (3,065 reviews)
"Overall the stay was great. Staff were very helpful. We had some issues with the room carpet but it was taken care of as soon as I reported to the front desk. I very much recommend this place."
United States
Lucia
Regal Oaks Resort Vacation Townhomes by IDILIQ
Interior

Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse

Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse
3.0 star property
Loughman
The price is S$1,100
includes taxes & fees
22 Feb - 23 Feb
Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse
In-room dining

FL- 1904 Nice Ct

FL- 1904 Nice Ct
3.0 star property
Kissimmee
The price is S$633
includes taxes & fees
18 Feb - 19 Feb
FL- 1904 Nice Ct
Outdoor pool

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
3.0 star property
Kissimmee
The price is S$356
includes taxes & fees
21 Feb - 22 Feb
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
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

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

10/10 Excellent
"Went for a long weekend with 3 young children aged 2-7. Stayed in a 2 bedroom villa. Very accommodating and provided a crib and high chair for our stay, also a few dishwasher pods and laundry soap which was really convenient! Villa was newly renovated and spotless. We loved the pools (heated)!, great for all ages of our children. Pool bars and food were great also! Would definitely stay again!"
Claire Mary 3-night trip
Posted 13 hours ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

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 66 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.