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Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winter Haven vacation rentals

A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

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

Hook, Line & Leisure: Lakefront Gem w/ Porch!
3.0 star property
Florence Villa
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 NT$5,206
NT$12,746 total
includes taxes & fees
Sep 9 - Sep 10
Hook, Line & Leisure: Lakefront Gem w/ Porch!
A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

2. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (6 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
The price is NT$1,892
NT$7,878 total
includes taxes & fees
Sep 9 - Sep 10
BlockHaven near Legoland & Disney
A swimming pool with a fence, lounge chairs, and a palm tree.

3. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
The price is NT$2,243
NT$2,512 total
includes taxes & fees
Sep 9 - Sep 10
Lake Ida Beach Resort
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a built-in oven.

4. Legoland & Lakes Pool Home w/ Private Suite

Legoland & Lakes Pool Home w/ Private Suite
3.0 star property
Winter Haven
The price is NT$4,606
NT$15,965 total
includes taxes & fees
Sep 25 - Sep 26
Legoland & Lakes Pool Home w/ Private Suite
A modern reception area with a wooden panel design, a tiled floor, and a white door in the background.

5. Elita Inn

Elita Inn
3.0 star property
Dundee
7.4 out of 10, Good, (33 reviews)
"Very nice accommadations..friendly staff"
United States
lance
The price is NT$2,839
NT$3,180 total
includes taxes & fees
Sep 9 - Sep 10
Elita Inn
A modern kitchen with white cabinetry, granite countertops, stainless steel appliances, and a wooden floor.

6. Modern Dundee Townhome Near Lakes & Legoland!

Modern Dundee Townhome Near Lakes & Legoland!
3.5 star property
Dundee
The price is NT$4,164
NT$11,148 total
includes taxes & fees
Sep 9 - Sep 10
Modern Dundee Townhome Near Lakes & Legoland!
A golf course with a large rock formation, palm trees, and a well-maintained green.

7. 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, (578 reviews)
"First time experience. The stay was pretty good."
United States
Anquanice
The price is NT$3,147
NT$4,180 total
includes taxes & fees
Sep 10 - Sep 11
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
A modern kitchen with dark cabinets, stainless steel appliances, a marble floor, and a bar area with stools.

8. The Grand Retreat at CG with pool

The Grand Retreat at CG with pool
4.0 star property
Champions Gate
The price is NT$3,135
NT$12,234 total
includes taxes & fees
Sep 21 - Sep 22
The Grand Retreat at CG with pool
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

9. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (4,995 reviews)
"It's is a very nice resort my family enjoyed it and use way they rooms are designed is awesome you can get a little privacy from your kids and love ones at the same time."
United States
Vernon
The price is NT$2,131
NT$3,210 total
includes taxes & fees
Sep 13 - Sep 14
Vacation Village Orlando, Celebration
A covered outdoor seating area with sofas and chairs, large windows, and a ceiling fan.

10. Solara Resort Home With Private Pool Near Disney

Solara Resort Home With Private Pool Near Disney
3.0 star property
Kissimmee
The price is NT$3,092
NT$10,277 total
includes taxes & fees
Sep 9 - Sep 10
Solara Resort Home With Private Pool Near Disney
A riverside cabin with a dock, surrounded by lush greenery and a cloudy sky.

11. Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (223 reviews)
"Camp Mack is an awesome place for getting away for a few days or longer. The surroundings are beautiful, and the people are so friendly."
United States
Terri
The price is NT$3,373
NT$3,778 total
includes taxes & fees
Sep 9 - Sep 10
Camp Mack Lodge, Marina & RV Resort
A resort with a central pool, palm trees, and a view of the surrounding buildings.

12. 1520 FD Champions Gate

1520 FD Champions Gate
3.5 star property
Champions Gate
The price is NT$5,934
NT$18,609 total
includes taxes & fees
Sep 10 - Sep 11
1520 FD Champions Gate
A room with a bed, a table with a plant, a lamp, and a window with curtains.

13. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
The price is NT$3,123
NT$6,374 total
includes taxes & fees
Sep 9 - Sep 10
Lyrios Vacation Rentals - The Palms
A building with a sign reading "High Point World Resort Welcome Center."

14. High Point World Resort

High Point World Resort
3.5 star property
Kissimmee
8.8 out of 10, Excellent, (175 reviews)
"great place to stay!"
United States
Dylan
The price is NT$4,401
NT$4,995 total
includes taxes & fees
Sep 9 - Sep 10
High Point World Resort
An aerial view of a resort with multiple swimming pools, lounge areas, and palm trees.

15. Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1,620 reviews)
"Great stay! Will visit again."
United States
RYAN
The price is NT$7,266
NT$9,742 total
includes taxes & fees
Sep 9 - Sep 10
Reunion Resort & Golf Club
A modern kitchen with a central island, bar stools, pendant lighting, and stainless steel appliances.

16. Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is NT$5,332
NT$13,536 total
includes taxes & fees
Oct 1 - Oct 2
Golf, Dine & Unwind Poolside! Haines City Getaway
A narrow hallway with beige walls, a white door at the end, and a white shelf on the right.

17. Mvy7664 - 3BR House Near Disney With Hot Tub

Mvy7664 - 3BR House Near Disney With Hot Tub
3.0 star property
Kissimmee
The price is NT$6,073
NT$14,163 total
includes taxes & fees
Sep 25 - Sep 26
Mvy7664 - 3BR House Near Disney With Hot Tub
A swimming pool with a hot tub, surrounded by a glass enclosure with a view of a residential area.

18. Harmony Ensuite Room Shared Home No Car

Harmony Ensuite Room Shared Home No Car
2.5 star property
Kissimmee
The price is NT$1,388
NT$4,082 total
includes taxes & fees
Sep 9 - Sep 10
Harmony Ensuite Room Shared Home No Car
A large swimming pool surrounded by palm trees and lounge chairs, with a view of residential buildings in the background.

19. Stylish 3BR Condo Championsgate w Water Park

Stylish 3BR Condo Championsgate w Water Park
3.0 star property
Davenport
The price is NT$3,324
NT$12,039 total
includes taxes & fees
Sep 9 - Sep 10
Stylish 3BR Condo Championsgate w Water Park
A swimming pool with palm trees, a water slide, and a building with an arched entrance.

20. Spacious Townhome Near Disney, Free Parking

Spacious Townhome Near Disney, Free Parking
3.5 star property
Regal Palms
8.0 out of 10, Very Good, (1 review)
"The unit was clean. The host was responsive. The resort property was fun and welcoming. Definitely enjoyed the pool area. Location was pretty good for all the things we wanted to do. The check-in check-out process was pretty smooth. I would definitely stay here again when I visit this area."
United States
Marquita
The price is NT$2,555
NT$9,540 total
includes taxes & fees
Sep 9 - Sep 10
Spacious Townhome Near Disney, Free Parking
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Ok"
Evelyn 6-night trip
Posted 1 hour ago
The Grove Resort & Water Park 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:

  • View our selection of featured holiday rentals in Winter Haven
  • Use the map to find apartments and other holiday homes in the Winter Haven neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter Haven while they last

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?

Formosa Valley Resort by UNE Homes: This vacation home rental outside of Winter Haven is equipped with an outdoor pool, air-conditioning, and free WiFi to help you feel comfortable during your stay. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

How many vacation rentals are there in Winter Haven?

Choose from 60 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 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 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.