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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Lakeland - Winter Haven villas

A water park with a large pool, palm trees, and a view of a lake.

1. Upstay Modern Home Near Disney With Pool

Upstay Modern Home Near Disney With Pool
3.0 star property
Kissimmee
The price is ￥19,734
￥56,456 total
includes taxes & fees
Oct 5 - Oct 6
Upstay Modern Home Near Disney With Pool
A balcony with two blue cushioned chairs, a glass door leading to a bedroom, and a view of a grassy area and buildings in the distance.

2. Stylish 3BR Condo Championsgate w Water Park

Stylish 3BR Condo Championsgate w Water Park
3.0 star property
Davenport
The price is ￥17,207
￥60,891 total
includes taxes & fees
Oct 7 - Oct 8
Stylish 3BR Condo Championsgate w Water Park
A residential house with a tiled roof, a palm tree, and a car parked in the driveway.

3. 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, (9 reviews)
"It was an ok visit "
United States
Cordell G.
The price is ￥22,494
￥52,092 total
includes taxes & fees
Oct 5 - Oct 6
Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion
Al fresco dining meets resort-style privacy in this beautifully landscaped outdoor living space

4. LuxuryResort~MagicVillage~Ensuite Baths~NearDisney

LuxuryResort~MagicVillage~Ensuite Baths~NearDisney
Kissimmee
The price is ￥7,487
￥76,352 total
includes taxes & fees
Oct 25 - Oct 26
LuxuryResort~MagicVillage~Ensuite Baths~NearDisney
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

5. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is ￥10,229
￥48,274 total
includes taxes & fees
Oct 6 - Oct 7
Amazing Spider | Disney, Slides & River
Exterior

6. Location! 1.4 miles to Disney - Orlando Family Home

Location! 1.4 miles to Disney - Orlando Family Home
Kissimmee
9.6 out of 10, Exceptional, (47 reviews)
"Great location and space and gist was great"
United States
terri
The price is ￥18,232
￥61,679 total
includes taxes & fees
Oct 20 - Oct 21
Location! 1.4 miles to Disney - Orlando Family Home
A residential neighborhood with houses, a driveway, and a parked car.

7. Your Disney Dream Stay 5BR Villa + Private Pool

Your Disney Dream Stay 5BR Villa + Private Pool
Marbella
8.0 out of 10, Very good, (4 reviews)
"Only issue was not having any water pressure our last night in the house 11/1/2025. Returned to house around 10:30pm and had no pressure to take showers. Other than that, great house and host was good other than the last night issue "
United States
Bryan l.
The price is ￥12,707
￥60,041 total
includes taxes & fees
Oct 5 - Oct 6
Your Disney Dream Stay 5BR Villa + Private Pool
A two-story house with a red door, arched windows, and a tiled roof.

8. Power Up Palace | Disney, River & Slides

Power Up Palace | Disney, River & Slides
Kissimmee
The price is ￥10,229
￥48,274 total
includes taxes & fees
Oct 14 - Oct 15
Power Up Palace | Disney, River & Slides
A modern townhouse with a flat roof, large windows, and a small patio area with outdoor seating.

9. 8761 ZD - 3 BD The Hub Paradise Cozy Place

8761 ZD - 3 BD The Hub Paradise Cozy Place
Four Corners
The price is ￥10,102
￥72,546 total
includes taxes & fees
Oct 12 - Oct 13
8761 ZD - 3 BD The Hub Paradise Cozy Place
A modern building with a parking lot, featuring a central entrance with glass doors and a small seating area.

10. Themed rooms - gated community

Themed rooms - gated community
Kissimmee
The price is ￥13,544
￥54,137 total
includes taxes & fees
Oct 26 - Oct 27
Themed rooms - gated community
An outdoor lounge area with multiple seating options, ceiling fans, and large windows offering views of palm trees and a beach.

11. Upstay Modern Solara Retreat w Games Room & Pool

Upstay Modern Solara Retreat w Games Room & Pool
3.0 star property
Kissimmee
The price is ￥19,290
￥55,756 total
includes taxes & fees
Oct 19 - Oct 20
Upstay Modern Solara Retreat w Games Room & Pool
A multi-story residential building with a brick pathway, a small garden, and a tree.

12. Family Villa w Lazy River Near Disney

Family Villa w Lazy River Near Disney
2.0 star property
Regal Palms
The price is ￥16,550
￥65,266 total
includes taxes & fees
Oct 5 - Oct 6
Family Villa w Lazy River Near Disney
A two-story building with a symmetrical facade, a central entrance with a door, and a small porch area.

13. Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney

Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney
Regal Palms
The price is ￥7,607
￥88,800 total
includes taxes & fees
Oct 7 - Oct 8
Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

14. 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 ￥10,229
￥48,274 total
includes taxes & fees
Oct 8 - Oct 9
Shiny Legendary | Disney, River & Slides
Pool

15. 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
The price is ￥11,365
￥60,065 total
includes taxes & fees
Oct 5 - Oct 6
Family-Friendly Disney Villa - Private Pool, Spa & BBQ - 15 Min to Disney
An aerial view of a property with a swimming pool, a covered patio, and a large building with multiple windows.

16. Disney Villa with Hot Tub+Grill+Many other amenities

Disney Villa with Hot Tub+Grill+Many other amenities
Bridgewater Crossing
The price is ￥14,775
￥41,868 total
includes taxes & fees
Oct 15 - Oct 16
Disney Villa with Hot Tub+Grill+Many other amenities
A two-story house with a garage, stone accents, and a well-maintained lawn.

17. 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, (76 reviews)
"Everything was nice. We enjoyed our stay and would definitely recommend for future stays."
United States
Jalisa Y.
The price is ￥24,861
￥132,122 total
includes taxes & fees
Oct 5 - Oct 6
Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
A covered outdoor swimming pool with lounge chairs and a pergola structure.

18. Gorgeous VILLA near Disney, Private Heated South Pool

Gorgeous VILLA near Disney, Private Heated South Pool
Sandy Ridge
9.0 out of 10, Wonderful, (18 reviews)
"My family had a wonderful stay! Would definitely come back! "
United States
Janay P.
The price is ￥14,207
￥67,371 total
includes taxes & fees
Oct 14 - Oct 15
Gorgeous VILLA near Disney, Private Heated South Pool
A spacious outdoor area with a pool, wicker furniture, and a view of a residential neighborhood during sunset.

19. Enchanted Villa with Lake View 6-Bedroom in Resort

Enchanted Villa with Lake View 6-Bedroom in Resort
Lake Berkley
9.6 out of 10, Exceptional, (5 reviews)
"Amazing detail in the decor and easy to communicate host. So welcoming and great for large parties. I took my family of nine and there was more than enough room for everyone. "
United States
Sarah J.
The price is ￥24,151
￥79,872 total
includes taxes & fees
Nov 4 - Nov 5
Enchanted Villa with Lake View 6-Bedroom in Resort
An aerial view of a lakeside resort with a swimming pool, a castle-like structure, and surrounding residential areas.

20. 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 ￥12,154
￥47,677 total
includes taxes & fees
Oct 12 - Oct 13
Beach Resort near Disney with Poolside Tike Bar
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 Lakeland - Winter Haven Hotel Reviews

Hilton Vacation Club Mystic Dunes Orlando

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent
"😍"
Latorria 2-night trip
Posted less than an hour ago
Hilton Vacation Club Mystic Dunes Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Villas information

Number of reviews
146
Accommodation
309 Villas
Lowest Price
￥41,868
Highest Price
￥132,122

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?
Expect to pay between ￥41,868 and ￥132,122 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 309 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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