A baseball player in a white uniform with the number 20, a catcher in an orange uniform, and an umpire standing behind the catcher.

Search Villas in Lakeland - Winter Haven

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Lakeland - Winter Haven villas

Exterior

1. 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
9.0 out of 10, Wonderful, (7 reviews)
"It was an ok visit "
United States
Cordell G.
The price is ￥20,843
￥49,035 total
includes taxes & fees
Sep 25 - Sep 26
Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion
Villa (4 Bedrooms) | Interior

2. Spacious Townhome Near Disney, Free Parking

Spacious Townhome Near Disney, Free Parking
3.5 star property
Regal Palms
8.0 out of 10, Very Good, (1 review)
"The unit was clean. The host was responsive. The resort property was fun and welcoming. Definitely enjoyed the pool area. Location was pretty good for all the things we wanted to do. The check-in check-out process was pretty smooth. I would definitely stay here again when I visit this area."
United States
Marquita
The price is ￥12,506
￥46,689 total
includes taxes & fees
Sep 13 - Sep 14
Spacious Townhome Near Disney, Free Parking
Villa (4 Bedrooms) | Interior

3. 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 ￥15,686
￥61,481 total
includes taxes & fees
Sep 15 - Sep 16
Emerald Garden - Resort - 15 Min to Disney - Pets
Pool

4. Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater

Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater
Haines City
8.8 out of 10, Excellent, (91 reviews)
"Really enjoyed the house which was perfect for our family of nine people. The pool was really enjoyed by the kids and everyone had plenty of room to spread out for privacy. Only issues we had were a few blinds that need to be replaced and the tub in the master suite was not clean."
United States
dan l.
The price is ￥24,548
￥62,818 total
includes taxes & fees
Sep 13 - Sep 14
Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater
Exterior

5. 5BR Family Villa | Private Pool | Near Disney

5BR Family Villa | Private Pool | Near Disney
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 ￥12,428
￥58,725 total
includes taxes & fees
Sep 14 - Sep 15
5BR Family Villa | Private Pool | Near Disney
Terrace/patio

6. 🌿Welcome to the Jungle🌿

🌿Welcome to the Jungle🌿
Loughman
9.0 out of 10, Wonderful, (19 reviews)
"Hosts were great and very responsive! Our family loved our stay, house was nice and plenty of room for all of us! We would definitely stay here again! Thank you for being such great hosts!"
United States
Amanda P.
🌿Welcome to the Jungle🌿
Exterior

7. 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 ￥17,292
￥76,308 total
includes taxes & fees
Sep 16 - Sep 17
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Exterior

8. Amazing Villa with south facing pool and conservation view

Amazing Villa with south facing pool and conservation view
Watersong
9.8 out of 10, Exceptional, (221 reviews)
"Great communication. Nice pool and hot tub area."
United States
David V.
The price is ￥21,460
￥73,699 total
includes taxes & fees
Sep 23 - Sep 24
Amazing Villa with south facing pool and conservation view
House

9. Stylish 3BR Condo Championsgate w Water Park

Stylish 3BR Condo Championsgate w Water Park
3.0 star property
Davenport
The price is ￥16,265
￥58,916 total
includes taxes & fees
Sep 16 - Sep 17
Stylish 3BR Condo Championsgate w Water Park
Exterior

10. Sunkissed Paradise | Private Pool & Hot Tub

Sunkissed Paradise | Private Pool & Hot Tub
Trafalgar Village
9.0 out of 10, Wonderful, (2 reviews)
"Overall the villa was lovely, beautifully clean inside with nice touches like mini toiletries, large tub of ground coffee, sugar, creamer, plenty of toilet rolls salt and pepper, olive oil, coffee filters oh and a kettle bonus for us Brits.The Lounge, dining and bedrooms were beautifully furnished and had everything we needed. Plenty of bath towels, although could have done with a few more pool towels so we didn’t have to put them in the dryer after each use, but a minor detail.Frank was an...
United States
Sarah B.
The price is ￥16,983
￥63,899 total
includes taxes & fees
Sep 13 - Sep 14
Sunkissed Paradise | Private Pool & Hot Tub
Exterior

11. 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 ￥27,018
￥132,559 total
includes taxes & fees
Oct 4 - Oct 5
Villa with Heated Pool+Spa - Near Disney, Universal Studios and Beaches!
Villa (4 Bedrooms) | Interior

12. Solara Resort Home With Private Pool Near Disney

Solara Resort Home With Private Pool Near Disney
3.0 star property
Kissimmee
The price is ￥15,130
￥50,293 total
includes taxes & fees
Sep 15 - Sep 16
Solara Resort Home With Private Pool Near Disney
Exterior

13. Family Retreat @ Resort with Private Pool, 6Bdrm

Family Retreat @ Resort with Private Pool, 6Bdrm
Solterra Resort
9.0 out of 10, Wonderful, (30 reviews)
"Great place to stay!"
United States
Ken B.
Family Retreat @ Resort with Private Pool, 6Bdrm
Exterior

14. 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 ￥14,868
￥83,084 total
includes taxes & fees
Sep 22 - Sep 23
BBQ~Oasis w/Heated Pool~Marvel &Nemo rooms~Near Disney
Outdoor dining

15. 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.
Enchanted Villa with Lake View 6-Bedroom in Resort
Exterior

16. The ideal getaway II

The ideal getaway II
Kissimmee
The price is ￥12,737
￥56,615 total
includes taxes & fees
Sep 13 - Sep 14
The ideal getaway II
Pool

17. Gorgeous VILLA near Disney, Private Heated South Pool

Gorgeous VILLA near Disney, Private Heated South Pool
Sandy Ridge
9.0 out of 10, Wonderful, (17 reviews)
"My family had a wonderful stay! Would definitely come back! "
United States
Janay P.
The price is ￥13,895
￥64,658 total
includes taxes & fees
Sep 25 - Sep 26
Gorgeous VILLA near Disney, Private Heated South Pool
Exterior

18. 1556 PD - Poolside Bliss: Enchanted 4BR Townhome

1556 PD - Poolside Bliss: Enchanted 4BR Townhome
Champions Gate
9.0 out of 10, Wonderful, (2 reviews)
"We had a wonderful experience for our first time stay using a vrbo rental while attending our daughter's softball tournament. Our host responded to our(many) questions in a timely manner. The townhouse was lovely and clean. It was wonderful to have a pool to enjoy after a long day at the softball field. We would definitely stay again for next years tournament."
United States
Tanya A.
1556 PD - Poolside Bliss: Enchanted 4BR Townhome
Exterior

19. *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, (155 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 ￥20,534
￥63,703 total
includes taxes & fees
Sep 13 - Sep 14
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Exterior

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 ￥13,432
￥48,670 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Lakeland - Winter Haven Hotel Reviews

Embassy Suites By Hilton Orlando Sunset Walk

Embassy Suites By Hilton Orlando Sunset Walk

10/10 Excellent
"It was an excellent stay with the family for our Disney trip ."
Antonio 3-night trip
Posted 2 hours ago
Embassy Suites By Hilton Orlando Sunset Walk

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Villas information

Number of reviews
642
Accommodation
309 Villas
Lowest Price
￥46,689
Highest Price
￥132,559

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?
Expect to pay between ￥46,689 and ￥132,559 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.

Explore a world of travel with Expedia