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Check prices for these dates

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

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 AU$514
includes taxes & fees
19 Oct - 20 Oct
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 AU$555
includes taxes & fees
7 Oct - 8 Oct
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 AU$473
includes taxes & fees
6 Oct - 7 Oct
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 AU$692
includes taxes & fees
25 Oct - 26 Oct
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 AU$444
includes taxes & fees
6 Oct - 7 Oct
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 AU$544
includes taxes & fees
20 Oct - 21 Oct
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 AU$545
includes taxes & fees
6 Oct - 7 Oct
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 AU$443
includes taxes & fees
14 Oct - 15 Oct
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 AU$640
includes taxes & fees
12 Oct - 13 Oct
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
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 AU$512
includes taxes & fees
1 Nov - 2 Nov
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
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 AU$815
includes taxes & fees
7 Oct - 8 Oct
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 AU$444
includes taxes & fees
8 Oct - 9 Oct
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 AU$563
includes taxes & fees
21 Oct - 22 Oct
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 AU$387
includes taxes & fees
15 Oct - 16 Oct
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 AU$1,185
includes taxes & fees
6 Oct - 7 Oct
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 AU$604
includes taxes & fees
14 Oct - 15 Oct
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 AU$553
includes taxes & fees
6 Oct - 7 Oct
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 AU$434
includes taxes & fees
12 Oct - 13 Oct
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 1 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
286 Villas
Lowest Price
AU$387
Highest Price
AU$1,185

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?
Villas in Lakeland - Winter Haven cost between AU$387 and AU$1,185 per night. These getaways offer the privacy to enjoy your own space at a price that fits your budget. This price was 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 your pick of 286 villas in Lakeland - Winter Haven. Whether you're getting away with your family or close friends, and wherever your travels take you, Expedia makes it easy to find the perfect space.
What is there to do near my villa in Lakeland - Winter Haven?
Whether you're here for dining, sightseeing, museums or malls, Lakeland - Winter Haven offers something for everyone! The top city of Lakeland has lots of things to do and see, including Polk Museum of Art, Polk Theatre and Explorations V Children s Museum. If you're headed to Winter Haven, Theatre Winter Haven, Indigos Billiards, Bowling & Games and Chain of Lakes Park have to be on your itinerary.

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