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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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, 7, (7 reviews)
"It was an ok visit "
United States
Cordell G.
The price is ￥21,889
￥50,539 total
includes taxes & fees
Sep 15 - Sep 16
Peacefull villa in Lake Marion Golf Resort,all amenite,35' to the park atraccion
Pool

2. 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, 91, (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 ￥24,424
￥62,501 total
includes taxes & fees
Sep 15 - Sep 16
Paradise at Tower Lake 6 bedrooms with swimming pool/spa and movie theater
Terrace/patio

3. 🌿Welcome to the Jungle🌿

🌿Welcome to the Jungle🌿
Loughman
9.0 out of 10, 19, (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🌿
Villa (4 Bedrooms) | Interior

4. Upstay Modern Home Near Disney With Pool

Upstay Modern Home Near Disney With Pool
3.0 star property
Kissimmee
The price is ￥19,508
￥55,145 total
includes taxes & fees
Sep 15 - Sep 16
Upstay Modern Home Near Disney With Pool
Villa (4 Bedrooms) | Interior

5. 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, 1, (1 review)
The price is ￥15,606
￥61,168 total
includes taxes & fees
Sep 17 - Sep 18
Emerald Garden - Resort - 15 Min to Disney - Pets
Exterior

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

Family Retreat @ Resort with Private Pool, 6Bdrm
Solterra Resort
9.0 out of 10, 30, (30 reviews)
"Great place to stay!"
United States
Ken B.
The price is ￥10,906
￥63,067 total
includes taxes & fees
Sep 15 - Sep 16
Family Retreat @ Resort with Private Pool, 6Bdrm
Exterior

7. Sunkissed Paradise | Private Pool & Hot Tub

Sunkissed Paradise | Private Pool & Hot Tub
Trafalgar Village
9.0 out of 10, 2, (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 ￥16,897
￥63,883 total
includes taxes & fees
Sep 15 - Sep 16
Sunkissed Paradise | Private Pool & Hot Tub
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, 221, (221 reviews)
"Great communication. Nice pool and hot tub area."
United States
David V.
The price is ￥21,352
￥73,327 total
includes taxes & fees
Sep 23 - Sep 24
Amazing Villa with south facing pool and conservation view
Exterior

9. Luxury 5BR Family Villa Near Disney

Luxury 5BR Family Villa Near Disney
Champions Gate
9.0 out of 10, 2, (2 reviews)
"Rooms were real clean and the host were great, amazing communication."
United States
Darion W.
The price is ￥9,831
￥85,988 total
includes taxes & fees
Sep 15 - Sep 16
Luxury 5BR Family Villa Near Disney
Pool

10. 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 ￥11,060
￥58,452 total
includes taxes & fees
Sep 15 - Sep 16
Family-Friendly Disney Villa - Private Pool, Spa & BBQ - 15 Min to Disney
Exterior

11. 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, 12, (12 reviews)
"House was big enough for the whole family nice pool great area "
United States
Chrystal S.
The price is ￥14,747
￥72,825 total
includes taxes & fees
Sep 28 - Sep 29
Spacious Luxurious 6 Bedroom 5 Bath Villa Sleeps 12 Pool, Jacuzzi, near Disney
Exterior

12. 5BR Family Villa | Private Pool | Near Disney

5BR Family Villa | Private Pool | Near Disney
Marbella
8.0 out of 10, 4, (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 ￥14,132
￥60,894 total
includes taxes & fees
Sep 29 - Sep 30
5BR Family Villa | Private Pool | Near Disney
Exterior

13. Welcome To Our Beautiful Villa In The Gorgeous Community Solterra!

Welcome To Our Beautiful Villa In The Gorgeous Community Solterra!
Solterra Resort
9.8 out of 10, 218, (218 reviews)
"Hot tub and pool were great, very spacious place, would highly recommend "
United States
Jeffrey H.
The price is ￥24,424
￥81,315 total
includes taxes & fees
Sep 16 - Sep 17
Welcome To Our Beautiful Villa In The Gorgeous Community Solterra!
Villa (4 Bedrooms) | Interior

14. Solara Resort Home With Private Pool Near Disney

Solara Resort Home With Private Pool Near Disney
3.0 star property
Kissimmee
The price is ￥15,054
￥50,037 total
includes taxes & fees
Sep 15 - Sep 16
Solara Resort Home With Private Pool Near Disney
Exterior

15. Beach Resort near Disney with Poolside Tike Bar

Beach Resort near Disney with Poolside Tike Bar
Bahama Bay
9.6 out of 10, 4, (4 reviews)
"Love it"
United States
Jerome S.
The price is ￥11,828
￥46,396 total
includes taxes & fees
Sep 15 - Sep 16
Beach Resort near Disney with Poolside Tike Bar
Exterior

16. *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, 155, (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 ￥20,430
￥63,381 total
includes taxes & fees
Sep 15 - Sep 16
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Exterior

17. 1556 PD - Poolside Bliss: Enchanted 4BR Townhome

1556 PD - Poolside Bliss: Enchanted 4BR Townhome
Champions Gate
9.0 out of 10, 2, (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.
The price is ￥15,668
￥90,071 total
includes taxes & fees
Sep 15 - Sep 16
1556 PD - Poolside Bliss: Enchanted 4BR Townhome
Exterior

18. 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, 14, (14 reviews)
"Lots of space great for families! Great communication with host! Would stay again. "
Canada
Heather
The price is ￥14,240
￥82,077 total
includes taxes & fees
Sep 22 - Sep 23
BBQ~Oasis w/Heated Pool~Marvel &Nemo rooms~Near Disney
Pool

19. Gorgeous VILLA near Disney, Private Heated South Pool

Gorgeous VILLA near Disney, Private Heated South Pool
Sandy Ridge
9.0 out of 10, 17, (17 reviews)
"My family had a wonderful stay! Would definitely come back! "
United States
Janay P.
The price is ￥12,442
￥64,012 total
includes taxes & fees
Sep 25 - Sep 26
Gorgeous VILLA near Disney, Private Heated South Pool
House

20. Stylish 3BR Condo Championsgate w Water Park

Stylish 3BR Condo Championsgate w Water Park
3.0 star property
Davenport
The price is ￥16,372
￥58,832 total
includes taxes & fees
Sep 20 - Sep 21
Stylish 3BR Condo Championsgate w Water Park
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

8/10 Good
"It is a great place to have a group of people visit. Pools were nice and clean. Lots of love bugs this time of year."
Elizabeth 3-night trip
Posted 1 hour ago
The Grove Resort & Water Park Orlando

Find out more about Lakeland - Winter Haven

Lakeland - Winter Haven Villas information

Number of reviews
567
Accommodation
309 Villas
Lowest Price
￥46,396
Highest Price
￥90,071

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?
Expect to pay between ￥46,396 and ￥90,071 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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