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Check prices for these dates

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

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.
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 NZ$575
includes taxes & fees
17 Oct - 18 Oct
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 NZ$571
includes taxes & fees
5 Nov - 6 Nov
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 NZ$551
includes taxes & fees
13 Oct - 14 Oct
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.
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 NZ$667
includes taxes & fees
13 Oct - 14 Oct
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 NZ$708
includes taxes & fees
25 Oct - 26 Oct
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
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 NZ$790
includes taxes & fees
12 Oct - 13 Oct
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 NZ$541
includes taxes & fees
19 Oct - 20 Oct
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 NZ$1,466
includes taxes & fees
18 Oct - 19 Oct
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 NZ$465
includes taxes & fees
3 Nov - 4 Nov
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 NZ$754
includes taxes & fees
12 Oct - 13 Oct
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 NZ$472
includes taxes & fees
15 Oct - 16 Oct
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 NZ$538
includes taxes & fees
15 Oct - 16 Oct
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 NZ$735
includes taxes & fees
12 Oct - 13 Oct
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 NZ$874
includes taxes & fees
19 Oct - 20 Oct
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"The waterpark is super fun. Great for families"
Sarah 5-night trip
Posted less than an hour ago
The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Villas information

Number of reviews
144
Accommodation
309 Villas
Lowest Price
NZ$465
Highest Price
NZ$1,466

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?
Expect to pay between NZ$465 and NZ$1,466 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 favourite. Whether you're planning a family holiday or jet-setting with friends, Expedia has got you covered.
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 Centre and Publix Field at Joker Marchant Stadium. If you're escaping to Winter Haven, Indigo's Family Fun Centre, Chain of Lakes Park and Theatre Winter Haven are worth putting on your itinerary.

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