Winter Haven Vacation Rentals

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Jul 29 - Jul 30
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Vacation Rentals in Winter Haven

Vacation Village at Parkway
Relax by the resort's central pool, surrounded by lounge chairs and umbrellas.

Vacation Village at Parkway

3.0 star property
8.6 out of 10, Excellent, (2634)
"Very nice place to stay."
The price is P4,718
P6,327 total
includes taxes & fees
Aug 5 - Aug 6
Vacation Village at Parkway
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Experience a luxurious atmosphere in our spacious lobby, surrounded by palm trees, large plants, and vibrant bird murals.

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1516)
"Wonderful property and location!"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Summer Bay Orlando by Exploria Resorts
Relax by the central pool surrounded by palm trees and lounge chairs.

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very Good, (5566)
"Great place to stay with family had a great time a lot of activities to do "
The price is P6,670
P9,307 total
includes taxes & fees
Aug 7 - Aug 8
Summer Bay Orlando by Exploria Resorts
Barefoot'n Resort Kissimmee Orlando
Stunning two-story home with a vibrant facade, front porch, and blue-trimmed door.

Barefoot'n Resort Kissimmee Orlando

2.5 star property
9.0 out of 10, Wonderful, (131)
"Great place, would definitely stay there again "
The price is P6,934
P8,584 total
includes taxes & fees
Aug 16 - Aug 17
Barefoot'n Resort Kissimmee Orlando
Reunion Resort & Golf Club
Surrounded by lush greenery and palm trees, this resort offers multiple pools and a lazy river.

Reunion Resort & Golf Club

5.0 star property
8.8 out of 10, Excellent, (1357)
"Great place for families"
The price is P13,037
P17,505 total
includes taxes & fees
Jul 30 - Jul 31
Reunion Resort & Golf Club
The Berkley, Orlando
Lobby

The Berkley, Orlando

4.0 star property
9.6 out of 10, Exceptional, (1861)
"Very nice property for family vacation)"
The price is P6,100
P7,511 total
includes taxes & fees
Aug 11 - Aug 12
The Berkley, Orlando
Regal Oaks Resort Vacation Townhomes by IDILIQ
Relax by the resort's curved pool, surrounded by palm trees and lounge chairs.

Regal Oaks Resort Vacation Townhomes by IDILIQ

4.0 star property
8.4 out of 10, Very Good, (2952)
"Great stay "
The price is P7,150
P19,398 total
includes taxes & fees
Jul 30 - Jul 31
Regal Oaks Resort Vacation Townhomes by IDILIQ
Formosa Valley Resort by UNE Homes
Relax by the pool surrounded by a spacious deck and comfortable seating.

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (162)
"We loved our stay in UNE HOMES! Very spacious, clean, bathroom in everyroom, big rooms, BIG KITCHEN! Will be back for sure."
The price is P9,564
P29,120 total
includes taxes & fees
Jul 30 - Jul 31
Formosa Valley Resort by UNE Homes
Encantada Resort Vacation Townhomes by IDILIQ
2 outdoor pools, pool umbrellas, sun loungers

Encantada Resort Vacation Townhomes by IDILIQ

3.0 star property
8.6 out of 10, Excellent, (1361)
"Very nice resort "
The price is P7,404
P16,809 total
includes taxes & fees
Aug 3 - Aug 4
Encantada Resort Vacation Townhomes by IDILIQ
Magic Village Yards, Trademark Collection by Wyndham
Relax by the pool surrounded by comfortable lounge chairs and umbrellas.

Magic Village Yards, Trademark Collection by Wyndham

4.0 star property
9.2 out of 10, Wonderful, (1144)
"Spacious accommodations near Disney, with some amenities. "
Magic Village Yards, Trademark Collection by Wyndham
Lifetime of Vacations Resort
Stroll along the paved walkway surrounded by lush greenery and tropical plants, leading to a charming covered seating area.

Lifetime of Vacations Resort

3.0 star property
9.4 out of 10, Exceptional, (142)
"Fairly quiet, beautiful view. We would 100% stay here again."
Lifetime of Vacations Resort
Grand Lake Resort
Enjoy serene views from the pier, where benches offer a peaceful spot to sit and take in the surroundings.

Grand Lake Resort

3.0 star property
9.2 out of 10, Wonderful, (131)
"Always a great place to stay"
Grand Lake Resort
Barefoot Suites
Surrounded by lush greenery, this dock extends over a serene body of water, offering a tranquil escape.

Barefoot Suites

3.0 star property
9.0 out of 10, Wonderful, (1759)
"Much better than the last stay there!"
Barefoot Suites
Champions Gate condos by UNE
Relax by the resort pool surrounded by lounge chairs and umbrellas, with a view of the Mediterranean-style architecture.

Champions Gate condos by UNE

4.0 star property
9.2 out of 10, Wonderful, (20)
"It was a great place to stay"
The price is P7,713
P19,129 total
includes taxes & fees
Jul 30 - Jul 31
Champions Gate condos by UNE
Summerville Vacation Homes by Columbia Management
Private kitchen

Summerville Vacation Homes by Columbia Management

4.0 star property
8.4 out of 10, Very Good, (151)
"Not enough parking "
Summerville Vacation Homes by Columbia Management
Royal Laguna Villas By Magical Memories
Lobby

Royal Laguna Villas By Magical Memories

3.5 star property
7.0 out of 10, Good, (2336)
"the apartment is comfortable and pleasant but the air conditioning does not work, there is only a ceiling fan in the main room and in the living room. They did not give us the card for the pool area and it was a problem to pay and get the lockbox code."
Royal Laguna Villas By Magical Memories
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Relax by the pool surrounded by palm trees and lounge chairs.

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

3.5 star property
9.2 out of 10, Wonderful, (478)
"Very nice hotel...Very safe and clean "
The price is P6,117
P7,718 total
includes taxes & fees
Aug 3 - Aug 4
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
Encore Resort
Relax by the pool surrounded by a patio area and comfortable lounge seating.

Encore Resort

4.0 star property
6.4 out of 10, (117)
"Great place "
Encore Resort
Villas At Regal Palms
Relax by the pool surrounded by lush palm trees and a beautifully maintained area.

Villas At Regal Palms

4.0 star property
8.4 out of 10, Very Good, (568)
"Great location."
Villas At Regal Palms
Bahama Bay Resort
Children can splash and play in this vibrant water area surrounded by lush greenery and palm trees.

Bahama Bay Resort

3.5 star property
8.6 out of 10, Excellent, (2086)
"It's a family place, were you feel comfortable and welcome."
Bahama Bay Resort
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

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"We only stayed one night but the room was clean and comfortable. We would definitely stay again. "
Jennifer 1-night trip
Posted 6 hours ago
Kompose Boutique Resort at Theme Parks

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 145 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.