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Nov 13 - Nov 15
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Our top choices for Lakeland - Winter Haven villas

A modern kitchen with wooden cabinets, stainless steel appliances, and a black countertop.

1. Family Getaway Near Disney w Resort Pool & Billiards

Family Getaway Near Disney w Resort Pool & Billiards
3.0 star property
Orlando
The price is ￥15,057
￥59,553 total
includes taxes & fees
Nov 5 - Nov 6
Family Getaway Near Disney w Resort Pool & Billiards
A swimming pool with a football on the edge, surrounded by a covered area with a view of trees and a building in the background.

2. 129 Seneca Point Trl

129 Seneca Point Trl
4.0 star property
Indian Point
The price is ￥17,117
￥62,601 total
includes taxes & fees
Nov 18 - Nov 19
129 Seneca Point Trl
A swimming pool with a hot tub, lounge chairs, and a glass-enclosed patio area.

3. Heated Pool Game Room Home Near Disney

Heated Pool Game Room Home Near Disney
2.0 star property
Aylesbury
The price is ￥27,601
￥69,206 total
includes taxes & fees
Nov 5 - Nov 6
Heated Pool Game Room Home Near Disney
A room with wicker furniture, a glass coffee table, and a view of a green lawn and trees.

4. Resort Villa, Pools Fun and relaxation/w Kingbed.

Resort Villa, Pools Fun and relaxation/w Kingbed.
Kissimmee
8.8 out of 10, Excellent, (32 reviews)
"Shannelle was extremely responsive, informative and friendly. Very nice accomodations. Pleasant stay. "
United States
Joel W.
The price is ￥12,838
￥36,947 total
includes taxes & fees
Dec 1 - Dec 2
Resort Villa, Pools Fun and relaxation/w Kingbed.
A residential house with a tiled roof, a palm tree, and a car parked in the driveway.

5. Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion

Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion
Kissimmee
9.2 out of 10, Wonderful, (10 reviews)
"It was an ok visit "
United States
Cordell G.
The price is ￥22,499
￥49,894 total
includes taxes & fees
Nov 10 - Nov 11
Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

6. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is ￥12,880
￥50,035 total
includes taxes & fees
Nov 10 - Nov 11
Amazing Spider | Disney, Slides & River
Exterior

7. Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom

Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom
Kissimmee
9.6 out of 10, Exceptional, (47 reviews)
"Great location and space and gist was great"
United States
terri
The price is ￥15,643
￥58,431 total
includes taxes & fees
Nov 18 - Nov 19
Every Bedroom Has Its Own Bathroom ~ 1.4 Miles to Disney`s Animal Kingdom
An aerial view of a resort with a large swimming pool, multiple lounge areas, and a winding water feature.

8. BBQ~Oasis w/Heated Pool~Marvel &Nemo rooms~Near Disney

BBQ~Oasis w/Heated Pool~Marvel &Nemo rooms~Near Disney
Kissimmee
10.0 out of 10, Exceptional, (14 reviews)
"Lots of space great for families! Great communication with host! Would stay again. "
Canada
Heather
The price is ￥10,162
￥80,635 total
includes taxes & fees
Nov 9 - Nov 10
BBQ~Oasis w/Heated Pool~Marvel &Nemo rooms~Near Disney
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

9. Shiny Legendary | Disney, River & Slides

Shiny Legendary | Disney, River & Slides
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Had some confusion with the address but the host was super quick to respond, apologize, and fix the problem. Great location. Super cute rooms. Clean. Host had lots of essentials already at the house for us. Any question or concern we had was responded to quickly and thoroughly. "
United States
Aren B.
The price is ￥16,604
￥54,485 total
includes taxes & fees
Nov 16 - Nov 17
Shiny Legendary | Disney, River & Slides
A two-story house with a garage, stone accents, and a well-maintained lawn.

10. Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!

Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
Davenport
9.0 out of 10, Wonderful, (78 reviews)
"This property was more than expected and we plan to come again because we loved the house and the resort."
United States
Kimberly J.
The price is ￥23,678
￥125,036 total
includes taxes & fees
Nov 5 - Nov 6
Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
A large, multi-story hotel with a central courtyard, surrounded by lush greenery and palm trees.

11. VRBO 5 Star Luxury Resort Villa close to Disney World with poolside bar

VRBO 5 Star Luxury Resort Villa close to Disney World with poolside bar
Reunion
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay."
United States
Everick
The price is ￥16,111
￥52,670 total
includes taxes & fees
Nov 5 - Nov 6
VRBO 5 Star Luxury Resort Villa close to Disney World with poolside bar
A view through a window with a palm tree logo, dense foliage, and a calm body of water.

12. Bahama Bay Resort - Grand Bahama Penthouse

Bahama Bay Resort - Grand Bahama Penthouse
2.0 star property
Bahama Bay
The price is ￥19,135
￥68,392 total
includes taxes & fees
Nov 10 - Nov 11
Bahama Bay Resort - Grand Bahama Penthouse
An aerial view of a lakeside resort with a swimming pool, a castle-like structure, and surrounding residential areas.

13. Beach Resort near Disney with Poolside Tike Bar

Beach Resort near Disney with Poolside Tike Bar
Bahama Bay
9.6 out of 10, Exceptional, (4 reviews)
"Love it"
United States
Jerome S.
The price is ￥11,594
￥43,701 total
includes taxes & fees
Nov 15 - Nov 16
Beach Resort near Disney with Poolside Tike Bar
Pool

14. Family-Friendly Disney Villa - Private Pool, Spa & BBQ - 15 Min to Disney

Family-Friendly Disney Villa - Private Pool, Spa & BBQ - 15 Min to Disney
Sandy Ridge
10.0 out of 10, Exceptional, (1 review)
"Loved our stay thank you for hosting us"
United States
Tammy W.
The price is ￥11,368
￥61,185 total
includes taxes & fees
Nov 10 - Nov 11
Family-Friendly Disney Villa - Private Pool, Spa & BBQ - 15 Min to Disney
An aerial view of a resort with multiple swimming pools, a dock, and lush greenery.

15. Cozy 3BD Townhouse Near Disney, Encantada Resort

Cozy 3BD Townhouse Near Disney, Encantada Resort
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"I was looking for a place to escape for a few days while getting my bathroom redone and the property checked all of the boxes. My wife was able to get some work done, my dog had more than enough space, and the location is minutes from the amusement parks and tons of restaurants.The property is gated, clean, and has multiple bedrooms and bathrooms for the larger families that need it. The host was more than attentive. Even when I was having issues with the television, he responded to my message...
United States
LEONARD W.
The price is ￥9,668
￥52,151 total
includes taxes & fees
Nov 10 - Nov 11
Cozy 3BD Townhouse Near Disney, Encantada Resort
A covered outdoor swimming pool with lounge chairs and a pergola structure.

16. Gorgeous VILLA near Disney, Private Heated South Pool

Gorgeous VILLA near Disney, Private Heated South Pool
Sandy Ridge
8.8 out of 10, Excellent, (21 reviews)
"My family had a wonderful stay! Would definitely come back! "
United States
Janay P.
The price is ￥15,057
￥65,679 total
includes taxes & fees
Nov 5 - Nov 6
Gorgeous VILLA near Disney, Private Heated South Pool
A residential house with a garage, a well-maintained lawn, and a palm tree.

17. *Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Kissimmee
9.6 out of 10, Exceptional, (162 reviews)
"It was a great stay. Easy check-in and check-out along with the cleanliness and location of the house made this a very pleasant stay!"
United States
bryan s.
The price is ￥21,681
￥63,066 total
includes taxes & fees
Nov 30 - Dec 1
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
A two-story house with a red garage, surrounded by a well-maintained lawn and trees.

18. Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney

Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Trafalgar Village
8.8 out of 10, Excellent, (12 reviews)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
The price is ￥15,157
￥71,538 total
includes taxes & fees
Nov 8 - Nov 9
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
A rooftop pool area with lounge seating and a pergola structure.

19. Disney World just 6 minutes away - Amazing 5 Star Resort in Paradise

Disney World just 6 minutes away - Amazing 5 Star Resort in Paradise
Reunion
9.6 out of 10, Exceptional, (19 reviews)
"Great place to stay with a family! "
United States
Medina H.
The price is ￥16,412
￥53,011 total
includes taxes & fees
Nov 11 - Nov 12
Disney World just 6 minutes away - Amazing 5 Star Resort in Paradise
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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Lakeland - Winter Haven and related destinations

Explore the family-friendly area of Lakeland - Winter Haven—lake views, baseball, and popular sights like LEGOLAND® Florida.

See all hotels in Lakeland - Winter Haven
A child lying on the ground with colorful confetti around, in front of a LEGO sign that reads "LEGO LAND FLORIDA".
Photo by Visit Central Florida
Open Photo by Visit Central Florida

Top reviews in Lakeland - Winter Haven

A modern multi-story residential building with a symmetrical facade, stone accents, and a central entrance.
Contemporary 4BR Townhome With Pool & Themed Rooms

Contemporary 4BR Townhome With Pool & Themed Rooms

Contemporary 4BR Townhome With Pool & Themed Rooms
Clermont

10/10 Excellent

Even better than what is shown
United States
Malyjah
Reviewed July 5, 2026
Contemporary 4BR Townhome With Pool & Themed Rooms

Frequently Asked Questions

How much do villas in Lakeland - Winter Haven cost?

Expect to pay between ￥9,668 and ￥27,601 per night for villas in Lakeland - Winter Haven. No matter your budget, a fantastic stay is just a few clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Lakeland - Winter Haven?

Take a look at our villas in Lakeland - Winter Haven and then book your favorite. Whether you're planning a family vacation or jet-setting with friends, Expedia has got you covered.

Why book your villa in Lakeland - Winter Haven with Expedia?

Booking a villa in Lakeland - Winter Haven is as simple as deciding on your travel dates and choosing an option that checks your boxes. Looking for something upscale or budget friendly, or a stay that also offers a pool and free WiFi? Use Expedia's search filters to narrow your results and find your perfect match.

How can I find cheap villas in Lakeland - Winter Haven?

The simplest way to compare cheap villas in Lakeland - Winter Haven is with Expedia's handy filter tool. Narrow your search by star rating, budget and amenities to discover unbeatable bargains in just a click or two.

What is there to do near my villa in Lakeland - Winter Haven?

Whether you like food, shopping, history or sightseeing, Lakeland - Winter Haven offers it all, and more! The well-known city of Lakeland has loads of activities and attractions, including Polk Museum of Art, RP Funding Center and Publix Field at Joker Marchant Stadium. If you're escaping to Winter Haven, Indigo's Family Fun Center, Chain of Lakes Park and Theatre Winter Haven are worth putting on your itinerary.

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