Winter Haven Vacation Rentals

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Our top choices for Winter Haven vacation rentals

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 P2,356
P13,882 total
includes taxes & fees
May 31 - Jun 1
BlockHaven near Legoland & Disney

Hook, Line & Leisure: Lakefront Gem w/ Porch!

Hook, Line & Leisure: Lakefront Gem w/ Porch!
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 P9,748
P26,140 total
includes taxes & fees
May 24 - May 25
Hook, Line & Leisure: Lakefront Gem w/ Porch!

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (193 reviews)
"Was probably once a great time place. Owner was nice. Night time neighborhood is a bit noisy guess it's just how people act now no respect for property."
United States
wade
The price is P4,866
P5,449 total
includes taxes & fees
Jun 3 - Jun 4
Lake Ida Beach Resort

Legoland & Lakes Pool Home Pet Friendly

Legoland & Lakes Pool Home Pet Friendly
3.0 star property
Winter Haven
The price is P10,550
P34,646 total
includes taxes & fees
May 25 - May 26
Legoland & Lakes Pool Home Pet Friendly

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,182 reviews)
The price is P3,991
P6,070 total
includes taxes & fees
May 26 - May 27
Vacation Village Orlando, Celebration

Aster Cove

Aster Cove
4.0 star property
Crescent Lakes
The price is P9,978
P34,260 total
includes taxes & fees
May 29 - May 30
Aster Cove

Family Friendly Davenport Pool Villa

Family Friendly Davenport Pool Villa
4.0 star property
Florida Pines
The price is P8,426
P31,982 total
includes taxes & fees
May 27 - May 28
Family Friendly Davenport Pool Villa

Explore & Relax: Chic & Cozy Retreat in Lakeland!

Explore & Relax: Chic & Cozy Retreat in Lakeland!
3.0 star property
Lakeland
10.0 out of 10, Exceptional, (1 review)
"We had a great time. The house was beautiful. Decor was beautiful and bedding comforting. I sleep so good. The house was family friendly and plenty of rooms. "
United States
Debra
The price is P6,405
P23,636 total
includes taxes & fees
May 29 - May 30
Explore & Relax: Chic & Cozy Retreat in Lakeland!

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 P12,195
P41,446 total
includes taxes & fees
Jun 2 - Jun 3
Lakeview 6Br W/ Pool, Hot Tub & Near Theme Parks

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (303 reviews)
"Clean room would book again, great service"
United States
Alexandra
The price is P7,476
P9,254 total
includes taxes & fees
May 25 - May 26
Barefoot'n Resort Kissimmee Orlando

Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (208 reviews)
"Camp Mack is a wonderful place to stay!"
United States
Tommy
The price is P6,585
P7,375 total
includes taxes & fees
May 24 - May 25
Camp Mack Lodge, Marina & RV Resort

Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.5 star property
Kissimmee
The price is P2,710
P12,280 total
includes taxes & fees
May 25 - May 26
Harmony Ensuite Room Shared Home No Car

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

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
4.0 star property
Kissimmee
10.0 out of 10, Exceptional, (3 reviews)
"Would stay again and so should you! "
United States
katie
The price is P5,811
P14,852 total
includes taxes & fees
May 27 - May 28
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Bright 3BR Resort Condo Near Disney + Pools

Bright 3BR Resort Condo Near Disney + Pools
3.0 star property
Davenport
The price is P4,997
P21,329 total
includes taxes & fees
Jun 1 - Jun 2
Bright 3BR Resort Condo Near Disney + Pools

Florida Breeze

Florida Breeze
4.0 star property
Bellavida
Florida Breeze

Doppio Westside

Doppio Westside
4.0 star property
Davenport
9.4 out of 10, Exceptional, (43 reviews)
"The property exceeded our expectations. There was communication with the host and the instructions provided were detailed and easy to navigate for a seamless stay. It was a quiet location close enough to the major parks. We will definitely look to stay here again when we return to Florida. The decor was clean and modern, felt like home away from home. "
United States
Cecilia
The price is P13,611
P32,576 total
includes taxes & fees
May 25 - May 26
Doppio Westside

Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo

Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is P7,372
P35,648 total
includes taxes & fees
May 27 - May 28
Paradise Breeze Cottage By Shine Villas Margaritaville Resort Orlando 4 Bedroom Condo

LOVELY LUXURY APARTMENT CLOSE DISNEY

LOVELY LUXURY APARTMENT CLOSE DISNEY
3.5 star property
Kissimmee
8.4 out of 10, Very Good, (8 reviews)
"Nice appartment, everything you needed and clean and modern"
United Kingdom
Martyn
The price is P6,735
P18,759 total
includes taxes & fees
May 27 - May 28
LOVELY LUXURY APARTMENT CLOSE DISNEY

Sunny Private Pool & Spa & Fenced Yard. Nr Parks

Sunny Private Pool & Spa & Fenced Yard. Nr Parks
4.5 star property
Indian Point
The price is P9,847
P34,142 total
includes taxes & fees
May 29 - May 30
Sunny Private Pool & Spa & Fenced Yard. Nr Parks

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,230 reviews)
"Excellent place to stay. Very clean with all the amenities. "
United States
Shari
The price is P7,194
P8,786 total
includes taxes & fees
May 25 - May 26
The Berkley, Orlando
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

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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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 54 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.