Search Villas in Lakeland - Winter Haven

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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured Villas in Lakeland - Winter Haven and around

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Smart TV, DVD player, books, stereo

*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works

9.6 out of 10, Exceptional, (108)
"We stayed for a quick birthday get away, no issues at all to review about. "
*Tinkerbells Castle 1* Private Pool & Spa Overlooking Lake & Disney Fire Works
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
A heated pool

Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI

8.6 out of 10, Excellent, (59)
"This stay allowed for a relaxing getaway. The house is in a great location and in a safe neighborhood. It’s very close to Disney for those traveling for that reason. The community amenities are great (pool, gym, lounge, etc). The house itself is very spacious and well decorated, with room to fit probably 20 people comfortably. There are some upkeep issues that show signs of wear and tear but this did not take away from the experience of the trip and my vacation as a whole. The host was receptive...
Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI
Emerald Island Resort 8 Bed Pool Villa
A heated pool

Emerald Island Resort 8 Bed Pool Villa

7.0 out of 10, Good, (2)
"Beautiful home. Very well kept. We really enjoyed this beautiful house! Highly recommend. 10/10 "
Emerald Island Resort 8 Bed Pool Villa
Be Our Guest House ~ A Unique Disney Experience in Itself ~ Star Wars & Frozen.
Exterior

Be Our Guest House ~ A Unique Disney Experience in Itself ~ Star Wars & Frozen.

10.0 out of 10, Exceptional, (235)
"Our stay at this vacation rental was fantastic and exceeded our expectations. My wife was especially impressed by the cleanliness—every room was spotless and well cared for, making for a truly relaxing getaway.The home had tons of great amenities. The game room was a hit with our kids—they spent hours playing air hockey, foosball, ping pong, and even a stand-up arcade game in the living room. Clearly, a lot of thought went into making this space fun and family-friendly.The host was great—super...
Be Our Guest House ~ A Unique Disney Experience in Itself ~ Star Wars & Frozen.
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
Outdoor pool, a heated pool

Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

10.0 out of 10, Exceptional, (171)
"We loved it. "
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
Modern Villa less than 10 minutes from Disney
Outdoor pool, a heated pool

Modern Villa less than 10 minutes from Disney

10.0 out of 10, Exceptional, (107)
"This was a last minute trip to Florida for sun and warmth after a long winter. The house was clean and super fun with the themed rooms and hidden Mickeys. We enjoyed sitting outside by the pool and walking the neighborhood. Our host was very responsive the couple of times we reached out. While we were not there for Orlando’s attractions, the proximity to all the city has to offer was perfect. "
Modern Villa less than 10 minutes from Disney
A 6 Bedroom Home at Solterra Resort with Pool & Spa with a Nice Lake View!
Outdoor pool, a heated pool

A 6 Bedroom Home at Solterra Resort with Pool & Spa with a Nice Lake View!

9.4 out of 10, Exceptional, (82)
"Our stay was very good, the listing was exactly as described. We had no issues with anything in the home and it was very well equipped. "
A 6 Bedroom Home at Solterra Resort with Pool & Spa with a Nice Lake View!
Harry Potter Villa 10 minutes from Disney
Interior

Harry Potter Villa 10 minutes from Disney

10.0 out of 10, Exceptional, (61)
"Amazing attention to detail with everything from the Harry Potter movies! Every day we noticed something new we didn't see before. Chris was very personable and a wonderful host! Would definitely stay again."
Harry Potter Villa 10 minutes from Disney
A Star Wars themed villa for fans young and old
Outdoor pool, a heated pool

A Star Wars themed villa for fans young and old

10.0 out of 10, Exceptional, (89)
"We had an amazing time. My daughter loved the pool and the hot tub was wonderful after those long days at Disney. The themed rooms were great. We didn't get a chance to explore the grounds this trip, but plan on returning in the future with scheduled "off days" from the parks. Chris was amazing and quick to respond to my texts before and during the trip. Highly recommended."
A Star Wars themed villa for fans young and old
Windsor Hills Resort 6 Bedroom South Facing Pool/ Spa Home Steps to the Magic
A heated pool

Windsor Hills Resort 6 Bedroom South Facing Pool/ Spa Home Steps to the Magic

10.0 out of 10, Exceptional, (108)
"We were a multigenerational group visiting Disney - 3 grandparents, two parents, and 3 kids age 5-11. The house a 15 minute easy drive to the parks with a huge Walmart about a mile away for groceries. The layout was great for our group, bedrooms were comfortable, and the kitchen was well stocked. The kids loved the game room and swam at both the house pool and the community pool. Owner was communicative and very nice. No complaints - we had a wonderful stay!"
Windsor Hills Resort 6 Bedroom South Facing Pool/ Spa Home Steps to the Magic
The Mandalori-Inn - South Pool, Conservation View!
A heated pool

The Mandalori-Inn - South Pool, Conservation View!

10.0 out of 10, Exceptional, (54)
"House was so well furnished & clean. Pool & hot tub were both great. Host was great at responding & answering any questions. "
The Mandalori-Inn - South Pool, Conservation View!
Magical Family Villa: 8-Bdrm, 5 Themed, Pool, Spa, Game Room, Arcade, Movie
Outdoor pool, a heated pool

Magical Family Villa: 8-Bdrm, 5 Themed, Pool, Spa, Game Room, Arcade, Movie

9.6 out of 10, Exceptional, (153)
"Very comfortable and spacious for my family of 24 people. The only thing was, it did not include enough towels/cloths. I think we only had 10 towels at most, so we had to go out and buy our own towels during our stay. Terrific area though, would love to stay there again in the future! "
Magical Family Villa: 8-Bdrm, 5 Themed, Pool, Spa, Game Room, Arcade, Movie
Princess, Pirate & Super Hero Rooms, Mickey Pool, Toys & Game Room For All Ages
Outdoor pool, a heated pool

Princess, Pirate & Super Hero Rooms, Mickey Pool, Toys & Game Room For All Ages

9.8 out of 10, Exceptional, (166)
"Everyone in our family was impressed with the property! We can’t say enough good things. It perfectly accommodated our party of 12, ages 8months- 65yrs for week that included Disney World. Everything was very clean, host was responsive when we needed help finding a couple random things. Community pool and playground were a big plus on down days!"
Princess, Pirate & Super Hero Rooms, Mickey Pool, Toys & Game Room For All Ages
Glenbrook Retreat-Come in as Guests and Leave as Friends
Outdoor pool, a heated pool

Glenbrook Retreat-Come in as Guests and Leave as Friends

9.6 out of 10, Exceptional, (179)
"My family and I loved our stay. The house is spacious, clean and is located in a great neighborhood . Would definitely stay here again. "
Glenbrook Retreat-Come in as Guests and Leave as Friends
Outdoor Movie System, Outdoor pool, 15 min. to Disney, Family friendly!
Indoor pool, outdoor pool

Outdoor Movie System, Outdoor pool, 15 min. to Disney, Family friendly!

9.2 out of 10, Wonderful, (69)
"Beautiful house, very clean. We enjoyed our stay. "
Outdoor Movie System, Outdoor pool, 15 min. to Disney, Family friendly!
Adventure Villa - Beauty & Beast Dining -Themed & Customize Rooms - Private Pool
Outdoor pool, a heated pool

Adventure Villa - Beauty & Beast Dining -Themed & Customize Rooms - Private Pool

9.8 out of 10, Exceptional, (220)
"Perfect house for family of 6 making a week-long trip to Disney. Parks were a quick 10-15 min drive and kids enjoyed the play room on our day off. "
Adventure Villa - Beauty & Beast Dining -Themed & Customize Rooms - Private Pool
LUXURY FOR YOU + Last-Minute-Rates: 2 Masters, Gas Grill, TV65" 4K & Game Room
Outdoor pool, a heated pool

LUXURY FOR YOU + Last-Minute-Rates: 2 Masters, Gas Grill, TV65" 4K & Game Room

9.6 out of 10, Exceptional, (138)
"Clean, comfy, and in a quiet neighborhood"
LUXURY FOR YOU + Last-Minute-Rates: 2 Masters, Gas Grill, TV65" 4K & Game Room
6 miles to Disney: Clean Family 4 Beds, 3.5 Bath, pool/hot tub, game room, grill
Outdoor pool, a heated pool

6 miles to Disney: Clean Family 4 Beds, 3.5 Bath, pool/hot tub, game room, grill

9.8 out of 10, Exceptional, (268)
"The villa was excellent, everything we needed to make an enjoyable trip. Communication with Lee was excellent and answered all questions quickly. We had no need to contact anyone during our stay as there was no fault with the property at all. We will definitely be rebooking "
6 miles to Disney: Clean Family 4 Beds, 3.5 Bath, pool/hot tub, game room, grill
Villa With Private Pool
Outdoor dining

Villa With Private Pool

9.4 out of 10, Exceptional, (93)
"The villa is in a well established location just off Hwy 27. It's close to various golf courses. The villa has 4 good size double bedrooms, 2 with en suite. We used the master suite with direct access to the pool. It has a nice sized walk in wardrobe and plenty of drawer space. The kitchen is well stocked with crockery, pans and cutlery. We dined in most nights. Fridge/freezer and modern cooker making it very easy to self cater. Washing machine and dryer are just off the kitchen in a cupboard...
Villa With Private Pool
“3 MILES TO DISNEY’S MAIN GATE” 5⭐️ 4BD 3BTH HOME with SOUTH FACING POOL+GAME RM
Exterior

“3 MILES TO DISNEY’S MAIN GATE” 5⭐️ 4BD 3BTH HOME with SOUTH FACING POOL+GAME RM

9.8 out of 10, Exceptional, (130)
"We loved the big, open floorplan. The pool was nice for afternoon relaxing. The neighborhood was great for walking. The only reasons we didn’t give this five stars is the master bedroom bedding needs to be replaced, and the kitchen was lacking a few essentials (especially a pizza cutter!)."
“3 MILES TO DISNEY’S MAIN GATE” 5⭐️ 4BD 3BTH HOME with SOUTH FACING POOL+GAME RM
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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Other property types in Lakeland - Winter Haven

Summer Bay Orlando by Exploria Resorts
5 outdoor pools

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5215)
"There was no cool water, only about 150 degrees, but once we told someone, the maintenance guy was there within the hour and fixed it. The place definitely has seen better days and looks rough in some spots but it was comfortable and convenient. "
The price is €145
includes taxes & fees
30 Mar - 31 Mar
Summer Bay Orlando by Exploria Resorts
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
Interior

Margaritaville Cottages Orlando with H2O Waterpark by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1247)
"We loved our stay!"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1701)
"This is the 5th time we have stayed. Bedroom layouts work great for us. "
The price is €215
includes taxes & fees
13 Mar - 14 Mar
The Berkley, Orlando
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.

Frequently asked questions

How much do villas in Lakeland - Winter Haven cost?
Expect to pay between and 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 221 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.
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 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.