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Winter Haven Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
$361 nightly
The price is $404
Sep 7 - Sep 8
Total with taxes and fees
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
$230 nightly
The price is $258
Sep 9 - Sep 10
Total with taxes and fees
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
$77 nightly
The price is $87
Sep 20 - Sep 21
Total with taxes and fees
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
$452 nightly
The price is $506
Sep 25 - Sep 26
Total with taxes and fees
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
$100 nightly
The price is $112
Sep 7 - Sep 8
Total with taxes and fees
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
$316 nightly
The price is $353
Sep 7 - Sep 8
Total with taxes and fees
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
$136 nightly
The price is $152
Sep 7 - Sep 8
Total with taxes and fees
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
$342 nightly
The price is $388
Sep 21 - Sep 22
Total with taxes and fees
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, (4,973 reviews)
"Enjoyed the stay booked again"
United States
Joseph
$93 nightly
The price is $106
Sep 10 - Sep 11
Total with taxes and fees
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
$287 nightly
The price is $326
Sep 8 - Sep 9
Total with taxes and fees
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, (222 reviews)
"Staff was amazing."
United States
Yaliuska
$96 nightly
The price is $108
Sep 13 - Sep 14
Total with taxes and fees
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
$509 nightly
The price is $578
Sep 8 - Sep 9
Total with taxes and fees
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
$177 nightly
The price is $201
Sep 26 - Sep 27
Total with taxes and fees
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
$155 nightly
The price is $176
Sep 7 - Sep 8
Total with taxes and fees
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, (1,619 reviews)
"Great stay! Will visit again."
United States
RYAN
$296 nightly
The price is $336
Sep 27 - Sep 28
Total with taxes and fees
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
$374 nightly
The price is $419
Sep 7 - Sep 8
Total with taxes and fees
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
$396 nightly
The price is $449
Sep 25 - Sep 26
Total with taxes and fees
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
$108 nightly
The price is $123
Oct 7 - Oct 8
Total with taxes and fees
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
$336 nightly
The price is $382
Sep 8 - Sep 9
Total with taxes and fees
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
$270 nightly
The price is $302
Sep 7 - Sep 8
Total with taxes and fees
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

8/10 Good
"I loved al of the amenities. The water park & pools were werth every dime. The only negatives were the $37 a day to park & $300 deposit that expedia didn't mention to me prior to my arrival. The deposit has to be on a bank card , prepaid or other cards won't be accepted. I still love the place and my family will be coming back next year"
Kevin 3-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

Find out more about Winter Haven

Everything you need to know about Winter Haven vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Haven vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Haven vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Haven vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Haven. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Haven in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Haven rentals

At Expedia, we put the best Winter Haven vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Haven rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Haven vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Haven. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.