Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Winter Haven vacation rentals

Outdoor pool, pool umbrellas, sun loungers

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (190 reviews)
"We have stayed here several times. "
United States
Martha
The price is ￥12,540
￥14,045 total
includes taxes & fees
Apr 5 - Apr 6
Lake Ida Beach Resort
House (3 Bedrooms) | 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 ￥27,143
￥69,565 total
includes taxes & fees
Apr 19 - Apr 20
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
Luxury House, 3 Bedrooms, Garden View | Living area | 50-inch Smart TV with digital channels, toys, heated floors

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Great communication with host. "
United States
Reid
The price is ￥14,008
￥44,667 total
includes taxes & fees
Apr 12 - Apr 13
BlockHaven near Legoland & Disney
Interior

Serene Lake Views: Winter Haven Home

Serene Lake Views: Winter Haven Home
3.0 star property
Winter Haven
Serene Lake Views: Winter Haven Home
Deluxe Room, 1 King Bed, Non Smoking

Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.0 star property
Kissimmee
The price is ￥6,670
￥18,681 total
includes taxes & fees
Apr 9 - Apr 10
Harmony Ensuite Room Shared Home No Car
House (3 Bedrooms) | Front of property

Lakefront Babson Park Escape: Pet Friendly!

Lakefront Babson Park Escape: Pet Friendly!
3.0 star property
Babson Park
Lakefront Babson Park Escape: Pet Friendly!
Exterior

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,788 reviews)
"Nice place to stay and close to the parks. "
United States
Kena
The price is ￥15,190
￥21,209 total
includes taxes & fees
Apr 7 - Apr 8
Vacation Village Orlando, Celebration
Lake

Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (206 reviews)
"Camp Mack is a wonderful place to stay!"
United States
Tommy
The price is ￥18,480
￥20,698 total
includes taxes & fees
Apr 5 - Apr 6
Camp Mack Lodge, Marina & RV Resort
Terrace/patio

Disney's Animal Kingdom Villas - Kidani Village

Disney's Animal Kingdom Villas - Kidani Village
4.0 star property
Bay Lake
9.0 out of 10, Wonderful, (167 reviews)
"The animals are amazing and the location for Animal Kingdom was perfect! The room was clean and comfortable."
United States
Kelly
Disney's Animal Kingdom Villas - Kidani Village
Outdoor pool

Orlando Getaway With Pool View Balcony

Orlando Getaway With Pool View Balcony
4.0 star property
Celebration
Orlando Getaway With Pool View Balcony
Interior entrance

Family Friendly Davenport Pool Villa

Family Friendly Davenport Pool Villa
4.0 star property
Florida Pines
The price is ￥39,214
￥103,005 total
includes taxes & fees
Apr 2 - Apr 3
Family Friendly Davenport Pool Villa
Lounge

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
10.0 out of 10, Exceptional, (1 review)
"Room was clean and ammenities were as advertised. "
United States
John
The price is ￥13,714
￥36,857 total
includes taxes & fees
Apr 2 - Apr 3
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
Exterior

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.2 out of 10, Wonderful, (250 reviews)
"We love staying at this resort, great area"
United States
Mary
The price is ￥15,028
￥19,038 total
includes taxes & fees
Apr 22 - Apr 23
Barefoot'n Resort Kissimmee Orlando
Exterior

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (1,892 reviews)
"Amazing place. "
Mexico
Ahmed
The price is ￥34,762
￥71,224 total
includes taxes & fees
Apr 21 - Apr 22
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Interior

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is ￥23,016
￥73,253 total
includes taxes & fees
Apr 4 - Apr 5
Serenity - Family & Pet Friendly, Amazing Location
Apartment (2 Bedrooms) | Interior

Pet-friendly Lakeland Condo w/ Screened Porch!

Pet-friendly Lakeland Condo w/ Screened Porch!
4.0 star property
Lakeland
Pet-friendly Lakeland Condo w/ Screened Porch!
Townhome, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Priceless Peace At Serenity By Shine Villas. 081 3 Bedroom Townhouse

Priceless Peace At Serenity By Shine Villas. 081 3 Bedroom Townhouse
3.0 star property
Clermont
Priceless Peace At Serenity By Shine Villas. 081 3 Bedroom Townhouse
Interior

4703 Flagler Beach Way, Kissimmee Florida,3bed

4703 Flagler Beach Way, Kissimmee Florida,3bed
3.0 star property
Kissimmee
4703 Flagler Beach Way, Kissimmee Florida,3bed
Floor plan

Bright 3BR Resort Condo Near Disney + Pools

Bright 3BR Resort Condo Near Disney + Pools
3.0 star property
Davenport
The price is ￥16,920
￥59,427 total
includes taxes & fees
Apr 12 - Apr 13
Bright 3BR Resort Condo Near Disney + Pools
Outdoor pool

Lakeview 6Br W/ Pool, Hot Tub & Near Theme Parks

Lakeview 6Br W/ Pool, Hot Tub & Near Theme Parks
4.5 star property
Lake Berkley
The price is ￥63,214
￥144,697 total
includes taxes & fees
Apr 12 - Apr 13
Lakeview 6Br W/ Pool, Hot Tub & Near Theme Parks
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

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

8/10 Good
"."
Jamie Marie 7-night trip
Posted 1 hour ago
Hilton Vacation Club Mystic Dunes Orlando

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 55 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 Indigo's Family Fun Center, 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.