Winter Haven Vacation Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Winter Haven Vacation Homes

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1630)
"The worst part is the traffic in the area"
The Berkley, Orlando

Solara Resort Gem - Pool, Game Room, Near Disney

9.2 out of 10, Wonderful, (14)
"Great place to stay very friendly needed a little TLC not much just generic maintenance. "
Solara Resort Gem - Pool, Game Room, Near Disney

Orlando Renters

3.5 star property
6.2 out of 10, (87)
"Very beautiful. Everything was nice and clean. I would recommend future guest to bring the own towels and extra toiletries. "
Orlando Renters

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (133)
"Clean and comfortable, food and shopping close by"
Formosa Valley Resort by UNE Homes

Encore Resort

4.0 star property
6.4 out of 10, (114)
"It was a very nice home. My family had a great time"
Encore Resort

Barbecue in Summer Kitchen, Smart TV by the Pool!

9.8 out of 10, Exceptional, (38)
"We had a wonderful stay at this house. Everything was as pictured. It is very roomy with enough space for all of us to have our own spaces. If travelling during the “cooler” months, I would highly suggest the pool heater as it cools down quickly. The pool was great for our toddler and other kids. Our toddler had a great time hanging out on the ledge playing with his toys. The only thing we came across was damp towels in the closet which wasn’t a huge deal as there is the washer and dryer....
Barbecue in Summer Kitchen, Smart TV by the Pool!

2022 Award @ Hosthub, Home Theater/Game Room/Harry Potter Rm Close to Disney

9.6 out of 10, Exceptional, (33)
"Good communication, was a great place for our family to stay as we explored Disney and Universal. This was our first time staying offsite from Disney and was a great location under 1/2 hour to all the parks. Do yourself a favor if staying here, go to the Eleven restaurant one night which is at the Reunion resort (11th floor) and 1/2 mile away. This place has a rooftop view of all the fireworks at Disney- DJ on Fridays and live music on Saturdays. We did this our final night and had awesome...
2022 Award @ Hosthub, Home Theater/Game Room/Harry Potter Rm Close to Disney

Kissimmee Maingate Area Pool Homes by SVV

3.5 star property
8.6 out of 10, Excellent, (338)
"The pool needs to be resurfaced. We didn’t let the kids swim in the pool because the pool was dirty and the cement on the bottom of the pool was breaking up. The house was clean and the location was perfect! We were hit with an unexpected registration charge of $207.00. It would if been nice to know about that hidden fee! Donnetta "
Kissimmee Maingate Area Pool Homes by SVV

Minutes from Disney! Lakefront villa with south facing pool and jacuzzi!

10.0 out of 10, Exceptional, (92)
"We really enjoyed the relaxing atmosphere of this home. Perfect for off days between park days. Plenty of room for a family with 2 king size beds and 2 twins!"
Minutes from Disney! Lakefront villa with south facing pool and jacuzzi!

Great quiet and comfortable, South Central Lakeland location.

9.8 out of 10, Exceptional, (124)
"I have stayed multiple times and enjoy each and every day. Very quiet, peaceful and excellent for clean. Will be back to stay in the future 😀"
The price is CA $101
CA $142 total
includes taxes & fees
Jan 16 - Jan 17
Great quiet and comfortable, South Central Lakeland location.

MO800 Champions Gate 5 Bedroom bathroom 5 Private Pool & Jaccuzi, Free Waterpark

9.0 out of 10, Wonderful, (66)
"Greatcstay"
MO800 Champions Gate 5 Bedroom bathroom 5 Private Pool & Jaccuzi, Free Waterpark

LUXE DISNEY HOME, POOL W/ SPA, GAME ROOM, FREE NETFLIX & WIFI

9.8 out of 10, Exceptional, (74)
"This was our second time renting the house. Nothing has changed since my first perfect experience. Quiet, clean and the host was very easy and quick to communicate with. Hope to be back again!"
LUXE DISNEY HOME, POOL W/ SPA, GAME ROOM, FREE NETFLIX & WIFI

Cozy house in charming Lakeland with AC, WiFi, really good quiet place.

10.0 out of 10, Exceptional, (2)
"Exactly what I was looking for"
The price is CA $72
CA $126 total
includes taxes & fees
Jan 10 - Jan 11
Cozy house in charming Lakeland with AC, WiFi, really good quiet place.

Marvelous Villa with Galactic Themed Bedroom at Encore

9.0 out of 10, Wonderful, (38)
"Property was just as advertised, spacious and comfortable in a new resort neighborhood. The kids, ages 4-10 had a blast in the Star Wars themed bedroom and garage game room. Pool was lovely even though we didn’t use much. Only a 20 minute ride to Disney parks and plenty of stores and restaurants nearby. Can’t say enough good things about resort staff from guards to management company. "
Marvelous Villa with Galactic Themed Bedroom at Encore

Outdoor TV, Air Hockey, Foosball, Epic Game Room, Basketball Arcade, 1GB: Summer Breeze

9.6 out of 10, Exceptional, (21)
"Great value and property. As advertised, thanks!"
Outdoor TV, Air Hockey, Foosball, Epic Game Room, Basketball Arcade, 1GB: Summer Breeze

The Bear's Den Resort Orlando

5.0 star property
7.8 out of 10, Good, (21)
"Brian W from the Bears Den reception committee is extremely helpful and great. "
The Bear's Den Resort Orlando

Big villa with private pool, game room! 3 Miles to Disney - Enhanced Cleaning

8.8 out of 10, Excellent, (116)
"Close to where we wanted to be, clean and spacious. The heated pool was AWESOME! "
The price is CA $244
CA $900 total
includes taxes & fees
Jan 6 - Jan 7
Big villa with private pool, game room! 3 Miles to Disney - Enhanced Cleaning

3 Bedrooms/ 3 Bathrooms/ The Hub (3205 TT)

10.0 out of 10, Exceptional, (13)
"It was a clean rental and well maintained. We had problems with some light fixtures in the kitchen being broken (not by us) when we got to the rental. I always like to check the whole property for any damages and we found that light broken hanging and shower doors weren’t installed properly etc but it is in a good neighborhood and close to most of the Disney world parks. The host would have good communication with us , as we explained what we had found when we got to the property. I would...
The price is CA $152
CA $602 total
includes taxes & fees
Jan 14 - Jan 15
3 Bedrooms/ 3 Bathrooms/ The Hub (3205 TT)

Stay near the magic! 3-bedroom home, just 6 minutes to Walt Disney World® Parks!

10.0 out of 10, Exceptional, (93)
"We came down for Disney for our daughters 6th birthday.Very last-minute booking but Jeannie was patient and worked with us. Its a home away from home. The layout is ideal with the master and kids room on the top floor. Having the heated pool in Dec is a cherry on top. Plenty of space for a larger group, beds are very comfortable and location for the home is ideal with the clubhouse just around the corner (walking and visiting with the ducks). Pool area is clean, great for the kids, DJ was on...
Stay near the magic! 3-bedroom home, just 6 minutes to Walt Disney World® Parks!

Sophisticated 4 En Suites w/ Private Hot Tub

9.8 out of 10, Exceptional, (10)
"We had a spectacular time in this home. It’s beautiful and it looks exactly like the pictures. We had everything that we needed and it’s in a great location. "
Sophisticated 4 En Suites w/ Private Hot Tub
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.
Don't see what you're looking for?
See all available properties in Winter Haven
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winter Haven

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5072)
"The property was exceptionally clean. It is very family friendly! The amenities were great. Bingo at the pool was so much fun! We ate on property several times and the food was delicious and reasonably priced. Also the customer service was superior. We really enjoyed our stay there and already looking forward to coming back next winter break! "
The price is CA $182
CA $250 total
includes taxes & fees
Jan 19 - Jan 20
Summer Bay Orlando by Exploria Resorts

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1145)
"nice place with perfect location. "
Margaritaville Resort Orlando Cottages by Rentyl

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1408)
"The property was very clean both inside and outside. The pools and hot tub in our area were great! A downside is that when you call for more towels you have to be in the room, they said they will not just leave it at your door. "
Vacation Village at Parkway
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.