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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Lakeland - Winter Haven villas

A hotel with a modern architectural design, featuring a large entrance with a covered walkway, palm trees, and a clear blue sky.

1. Fully-Equipped Villa Next to Disney!

Fully-Equipped Villa Next to Disney!
Kissimmee
9.2 out of 10, Wonderful, (85 reviews)
"Enjoyed a 5 day trip with my daughter. Great location, felt safe, lots of dining options and communication was good. I had everything I needed but mainly ate at restaurants as we were out and about."
United States
Shari W.
The price is ￥13,114
￥31,810 total
includes taxes & fees
Oct 13 - Oct 14
Fully-Equipped Villa Next to Disney!
A residential house with a tiled roof, a palm tree, and a car parked in the driveway.

2. 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 ￥22,515
￥52,142 total
includes taxes & fees
Oct 10 - Oct 11
Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion
A covered outdoor seating area with sofas and chairs, large windows, and a ceiling fan.

3. Solara Resort Home With Private Pool Near Disney

Solara Resort Home With Private Pool Near Disney
3.0 star property
Kissimmee
The price is ￥14,685
￥50,541 total
includes taxes & fees
Nov 5 - Nov 6
Solara Resort Home With Private Pool Near Disney
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

4. Amazing Spider | Disney, Slides & River

Amazing Spider | Disney, Slides & River
Kissimmee
8.0 out of 10, Very good, (1 review)
The price is ￥10,494
￥48,615 total
includes taxes & fees
Oct 13 - Oct 14
Amazing Spider | Disney, Slides & River
A residential neighborhood with houses, a driveway, and a parked car.

5. 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 ￥14,536
￥62,792 total
includes taxes & fees
Oct 20 - Oct 21
Your Disney Dream Stay 5BR Villa + Private Pool
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 ￥16,424
￥59,349 total
includes taxes & fees
Oct 13 - Oct 14
Location! 1.4 miles to Disney - Orlando Family Home
Pool

7. 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 ￥12,632
￥62,446 total
includes taxes & fees
Nov 9 - Nov 10
Family-Friendly Disney Villa - Private Pool, Spa & BBQ - 15 Min to Disney
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
BBQ~Oasis w/Heated Pool~Marvel &Nemo rooms~Near Disney
A two-story residential house with a front porch, a garage, and a well-maintained lawn.

9. Windsor Hills Resort/3Bedrm/Private Pool

Windsor Hills Resort/3Bedrm/Private Pool
Windsor Hills
The price is ￥22,095
￥83,099 total
includes taxes & fees
Oct 31 - Nov 1
Windsor Hills Resort/3Bedrm/Private Pool
A modern townhouse with a flat roof, large windows, and a small patio area with outdoor seating.

10. 8761 ZD - 3 BD The Hub Paradise Cozy Place

8761 ZD - 3 BD The Hub Paradise Cozy Place
Four Corners
The price is ￥10,106
￥72,570 total
includes taxes & fees
Oct 12 - Oct 13
8761 ZD - 3 BD The Hub Paradise Cozy Place
An aerial view of a resort with multiple swimming pools, a water slide, and a tower structure.

11. 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 ￥10,494
￥48,615 total
includes taxes & fees
Oct 19 - Oct 20
Shiny Legendary | Disney, River & Slides
A two-story house with a garage, stone accents, and a well-maintained lawn.

12. 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, (77 reviews)
"Everything was nice. We enjoyed our stay and would definitely recommend for future stays."
United States
Jalisa Y.
The price is ￥24,869
￥132,164 total
includes taxes & fees
Oct 18 - Oct 19
Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
A two-story house with a front porch, a mailbox, and a well-maintained garden with various plants and a palm tree.

13. Upstay Modern 3BR Townhome With Pool Near Disney

Upstay Modern 3BR Townhome With Pool Near Disney
3.5 star property
Kissimmee
The price is ￥12,608
￥41,031 total
includes taxes & fees
Nov 3 - Nov 4
Upstay Modern 3BR Townhome With Pool Near Disney
A spacious outdoor area with a pool, wicker furniture, and a view of a residential neighborhood during sunset.

14. 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 ￥14,378
￥68,888 total
includes taxes & fees
Oct 12 - Oct 13
Enchanted Villa with Lake View 6-Bedroom in Resort
An aerial view of a property with a swimming pool, a covered patio, and a large building with multiple windows.

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

Disney Villa with Hot Tub+Grill+Many other amenities
Bridgewater Crossing
The price is ￥14,789
￥42,540 total
includes taxes & fees
Oct 15 - Oct 16
Disney Villa with Hot Tub+Grill+Many other amenities
An aerial view of a lakeside resort with a swimming pool, a castle-like structure, and surrounding residential areas.

16. 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 ￥12,166
￥47,722 total
includes taxes & fees
Oct 12 - Oct 13
Beach Resort near Disney with Poolside Tike Bar
Interior

17. Emerald Garden - Resort - 15 Min to Disney - Pets

Emerald Garden - Resort - 15 Min to Disney - Pets
3.0 star property
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is ￥18,064
￥65,173 total
includes taxes & fees
Oct 12 - Oct 13
Emerald Garden - Resort - 15 Min to Disney - Pets
A single-story house with a garage, a front door, and a small front yard with a hedge.

18. 4701 Lakeview Pool Home off Hwy 192

4701 Lakeview Pool Home off Hwy 192
Lake Berkley
The price is ￥12,719
￥77,450 total
includes taxes & fees
Oct 20 - Oct 21
4701 Lakeview Pool Home off Hwy 192
A sunlit room with a large window, wicker furniture, a round decorative wall piece, and a view of a fenced field.

19. Family Retreat, Champions Gate Resort

Family Retreat, Champions Gate Resort
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Great host, great amenities. I enjoyed my stay with my family."
United States
ana m.
Family Retreat, Champions Gate Resort
A two-story building with a symmetrical facade, a central entrance with a door, and a small porch area.

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

Lazy River~Tiki Bar~Pool~Hot Tub~Themed~Disney
Regal Palms
Lazy River~Tiki Bar~Pool~Hot Tub~Themed~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.
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Top Lakeland - Winter Haven Hotel Reviews

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent
"Great stay"
Yosset 2-night trip
Posted less than an hour ago
Embassy Suites By Hilton Orlando Sunset Walk

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Villas information

Number of reviews
144
Accommodation
309 Villas
Lowest Price
￥31,810
Highest Price
￥132,164

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?
Expect to pay between ￥31,810 and ￥132,164 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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