A castle entrance with flags and banners, including a LEGO Kingdoms banner.

Winter Haven Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winter Haven vacation rentals

A swimming pool with a fence, lounge chairs, and a palm tree.

1. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (198 reviews)
"Clean room and private area loved it"
United States
Heather
$71 nightly
The price is $80
Oct 25 - Oct 26
Total with taxes and fees
Lake Ida Beach Resort
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, (8 reviews)
"Very nice house for a small family! Close to everything!"
United States
Yuliett
$214 nightly
The price is $240
Nov 12 - Nov 13
Total with taxes and fees
BlockHaven near Legoland & Disney
A dining area with a round table, two chairs, a view of a lake, and a decorative wall piece.

3. Lakefront Vibes w/ Lanai! Bird-watching Paradise

Lakefront Vibes w/ Lanai! Bird-watching Paradise
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
Oct 22 - Oct 23
Total with taxes and fees
Lakefront Vibes w/ Lanai! Bird-watching Paradise
A dark brown leather sectional sofa with multiple cushions, a carpeted floor, and two wall-mounted dog portraits.

4. 10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney

10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
2.0 star property
Winter Haven
$420 nightly
The price is $457
Oct 22 - Oct 23
Total with taxes and fees
10 min From Lego Land, the Chain of Lakes 45 min From Tampa& Disney
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
7.2 out of 10, Good, (37 reviews)
"Very nice accommadations..friendly staff"
United States
lance
$63 nightly
The price is $71
Oct 22 - Oct 23
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
Oct 22 - Oct 23
Total with taxes and fees
Modern Dundee Townhome Near Lakes & Legoland!
Room

7. Family Villa With Pool in Southern Dunes

Family Villa With Pool in Southern Dunes
2.0 star property
Haines City
$461 nightly
The price is $518
Oct 22 - Oct 23
Total with taxes and fees
Family Villa With Pool in Southern Dunes
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
$360 nightly
The price is $408
Nov 9 - Nov 10
Total with taxes and fees
The Grand Retreat at CG with pool
A golf course with a large rock formation, palm trees, and a well-maintained green.

9. 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, (582 reviews)
"Very nice and clean"
United States
Rob
$118 nightly
The price is $132
Oct 22 - Oct 23
Total with taxes and fees
Holiday Inn Club Vacations Orlando Breeze Resort by IHG
A large hotel complex with multiple high-rise buildings, a central swimming pool, and surrounding greenery.

10. Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (5,208 reviews)
"Awesome place to stay!"
United States
Richard Allen
$98 nightly
The price is $111
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village Orlando, Celebration
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, (225 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
$99 nightly
The price is $110
Oct 22 - Oct 23
Total with taxes and fees
Camp Mack Lodge, Marina & RV Resort
A covered outdoor area with a wooden picnic table and benches, a grill, and a ceiling fan.

12. Lyrios Vacation Rentals - The Palms

Lyrios Vacation Rentals - The Palms
4.0 star property
Kissimmee
$156 nightly
The price is $177
Oct 24 - Oct 25
Total with taxes and fees
Lyrios Vacation Rentals - The Palms
A thatched-roof gazebo with a wooden fence, surrounded by white lounge chairs on a sandy area.

13. Lifetime of Vacations Resort

Lifetime of Vacations Resort
3.0 star property
Kissimmee
9.4 out of 10, Exceptional, (185 reviews)
"We absolutely love coming to lifetime and grand lake resort. This is our favorite place to stay!!"
United States
Alena
$100 nightly
The price is $111
Oct 22 - Oct 23
Total with taxes and fees
Lifetime of Vacations Resort
A modern living room with a glass dining table, leather sofas, and a flat-screen TV.

14. Grand Lake Resort

Grand Lake Resort
3.0 star property
Kissimmee
9.2 out of 10, Wonderful, (271 reviews)
"Place was very clean and staff was a great help very friendly and helpful."
United States
Raymond
$93 nightly
The price is $105
Oct 22 - Oct 23
Total with taxes and fees
Grand Lake Resort
A two-story house with a porch, surrounded by palm trees and greenery.

15. Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (380 reviews)
"Nice rooms pool was great definitely will be back"
United States
Gilbert
$113 nightly
The price is $129
Oct 30 - Oct 31
Total with taxes and fees
Barefoot'n Resort Kissimmee Orlando
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

16. Walkable Dixieland District Gem With Yard

Walkable Dixieland District Gem With Yard
2.0 star property
Dixieland
$248 nightly
The price is $278
Oct 25 - Oct 26
Total with taxes and fees
Walkable Dixieland District Gem With Yard
A residential house with a beige exterior, a white garage door, and a front yard with leaf-covered ground.

17. Golfview Pool Home Southern Dunes

Golfview Pool Home Southern Dunes
2.0 star property
Haines City
$444 nightly
The price is $499
Oct 22 - Oct 23
Total with taxes and fees
Golfview Pool Home Southern Dunes
A swimming pool with palm trees, a water slide, and a building with an arched entrance.

18. 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
$262 nightly
The price is $294
Oct 22 - Oct 23
Total with taxes and fees
Spacious Townhome Near Disney, Free Parking
An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

19. Margaritaville Cottages Orlando by Rentyl with H2O Waterpark

Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
4.0 star property
Kissimmee
9.0 out of 10, Wonderful, (2,326 reviews)
"The cottages wonderful will book again"
United States
Cadine
$398 nightly
The price is $451
Oct 26 - Oct 27
Total with taxes and fees
Margaritaville Cottages Orlando by Rentyl with H2O Waterpark
Interior

20. Vista Grande - Resort&spa - 15 Min to Disney!

Vista Grande - Resort&spa - 15 Min to Disney!
3.0 star property
Bahama Bay
9.4 out of 10, Exceptional, (3 reviews)
"Condo was clean and comfortable, location and amenities were nice. "
United States
Jessica
$317 nightly
The price is $327
Oct 26 - Oct 27
Total with taxes and fees
Vista Grande - Resort&spa - 15 Min to Disney!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Haven Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

8/10 Good
"Main pool area is very nice with the hot tubs and sauna AND the bar but the lazy river area was closed both days we were there. They do not have a dryer available on property for all rooms and no balconies so I could not dry my clothes in between pool days. The showers did not have doors or curtains so I was cold in the shower and the floors stayed wet. The breakfast was amazing!"
Karen 2-night trip
Posted 8 hours ago
Kompose Boutique Resort at Theme Parks

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 $105 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 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 53 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 Peppa Pig Theme Park Florida, 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.