Winter Haven Vacation Rentals

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Check prices for these dates

Next weekend
Apr 18 - Apr 20
In two weeks
Apr 25 - Apr 27
In one month
May 9 - May 11
In two months
Jun 6 - Jun 8

Browse Select Winter Haven Vacation Homes

The Berkley, Orlando
Lobby sitting area

The Berkley, Orlando

4.0 star property
9.4 out of 10, Exceptional, (1738)
"We have stayed here twice now. This is a great location."
The price is CA $201
CA $241 total
includes taxes & fees
May 1 - May 2
The Berkley, Orlando
Formosa Valley Resort by UNE Homes
Private pool

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (146)
"This place was absolutely fantastic"
Formosa Valley Resort by UNE Homes
Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney
Exterior

Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney

10.0 out of 10, Exceptional, (57)
"Excellent property. Clean, great location within the Windsor Hills neighborhood as well as close to shopping, dining, and Disney World. Love the Windsor Hills development. Owner was easy to communicate with and responded promptly to any questions. "
Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney
The Adventure of a Lifetime! 5 BDR in Desirable Windsor Island Resort Sleeps 14
Pool

The Adventure of a Lifetime! 5 BDR in Desirable Windsor Island Resort Sleeps 14

10.0 out of 10, Exceptional, (9)
"Our family of 5 Grammy came (ages 6, 6, 2). We had a blast and it was nice to have a private pool with the public pool option as well. Lots of room for everyone to play and have fun. Communication with the host was easy and efficient!"
The Adventure of a Lifetime! 5 BDR in Desirable Windsor Island Resort Sleeps 14
Encore Resort
Outdoor pool

Encore Resort

4.0 star property
6.4 out of 10, (115)
"It was a very nice home. My family had a great time"
Encore Resort
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
Fridge, microwave, oven, stovetop

Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*

9.6 out of 10, Exceptional, (37)
"Our family had the best time here during our trip. Close to Disney and all other fun things to do. The hosts were absolutely wonderful in communication and helpfulness. We will definitely be returning next year. The home was spotless and we really enjoyed the heated pool. Had the best time."
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
Tropical villa overlooking the lake with a private pool, spa, grill, & AC
Pool

Tropical villa overlooking the lake with a private pool, spa, grill, & AC

8.2 out of 10, Very good, (34)
"Is too good . The house is very comfortable . "
Tropical villa overlooking the lake with a private pool, spa, grill, & AC
Single Story, Private Pool, Water Views, Game Room | Sleeps 11
Pool

Single Story, Private Pool, Water Views, Game Room | Sleeps 11

9.0 out of 10, Wonderful, (34)
"Great home. Tons to do. "
Single Story, Private Pool, Water Views, Game Room | Sleeps 11
ALWAYS FREE POOL AND SPA HEAT - Disney fireworks from pool/spa, Orange grove
Fridge, microwave, oven, stovetop

ALWAYS FREE POOL AND SPA HEAT - Disney fireworks from pool/spa, Orange grove

9.4 out of 10, Exceptional, (209)
"The stay was excellent. Accessible to the Disney parks with a view of the fireworks show (it is a small show since you are far away but still have a view of both displays). It is a little further of a drive for the Universal Studios parks. Would stay here again."
ALWAYS FREE POOL AND SPA HEAT - Disney fireworks from pool/spa, Orange grove
Pet-Friendly 5BR Single Level Home with Private Pool & Lake View | Near Disney | Game Room & Spa
Exterior

Pet-Friendly 5BR Single Level Home with Private Pool & Lake View | Near Disney | Game Room & Spa

8.6 out of 10, Excellent, (46)
"It was nice but the housekeeper didn’t do a good job and as a housekeeper my boss would have been upset. Pet hair everywhere sheets was not cleaned because it was pet hair in the bed and on the floor. Food crumbs everywhere. So it is safe to say that she did not do her job but overall the area and stores was awesome And the activities that me and my family had planned was close in the area, so it was nice "
Pet-Friendly 5BR Single Level Home with Private Pool & Lake View | Near Disney | Game Room & Spa
Beautiful home with white sand beach on stunning Crooked Lake
Sun loungers, beach towels

Beautiful home with white sand beach on stunning Crooked Lake

10.0 out of 10, Exceptional, (71)
"Very beautiful, clean "
Beautiful home with white sand beach on stunning Crooked Lake
Disney Themed Estate|Pool +Spa|Movie & Game Room
Terrace/patio

Disney Themed Estate|Pool +Spa|Movie & Game Room

9.8 out of 10, Exceptional, (188)
"Our stay at this Orlando-area rental home was truly exceptional. The location was perfect—just a short drive to Disney World, and conveniently close to natural springs and the Kennedy Space Center, making day trips effortless.Nestled in a serene and quiet neighborhood, the house provided a peaceful retreat after our adventures. Inside, we found the home to be impeccably clean and well-organized, equipped with everything we needed for a comfortable stay.The private pool was a highlight for our...
The price is CA $473
CA $1,137 total
includes taxes & fees
May 1 - May 2
Disney Themed Estate|Pool +Spa|Movie & Game Room
Kissimmee Maingate Area Pool Homes by SVV
Outdoor pool

Kissimmee Maingate Area Pool Homes by SVV

3.5 star property
8.6 out of 10, Excellent, (345)
"The inside of the house was beautiful. What I would recommend is anyone that rents should know that the essentials are not included such as salt pepper, toilet paper, paper towels. There were no dish towels no potholders no dish rack and no dish basin. The outside of the property could’ve used some TLC. The flower beds and the shrubs and trees could have been trimmed for a nicer appearance."
Kissimmee Maingate Area Pool Homes by SVV
Next to Disney Properties! PoolSpa Vacation Home Super Convenient Location
Outdoor pool, a heated pool

Next to Disney Properties! PoolSpa Vacation Home Super Convenient Location

8.8 out of 10, Excellent, (17)
"Booked a get away from the cold weather in Canada Love going to Florida each winter. Had a great spot. Easy to bike ride anywhere. Weather was lovely. A pool and hot tub, unfortunately do to a filter issue we did not have the use of them until after the 5th day. The host was GREAT at communicating with us and helped as much as possible. After getting the pool guy there all was fine. Was hoping for a discount on the first 5 days as the pool/spa cost 30 a day and we could not use them, I asked but...
Next to Disney Properties! PoolSpa Vacation Home Super Convenient Location
Upstay Disney Home w Pool & Cinema—ChampionsGate
Indoor pool

Upstay Disney Home w Pool & Cinema—ChampionsGate

Upstay Disney Home w Pool & Cinema—ChampionsGate
6BR Disney Home with 2 Master Suites, Pool & Hot Tub
Outdoor pool, a heated pool

6BR Disney Home with 2 Master Suites, Pool & Hot Tub

9.6 out of 10, Exceptional, (41)
"We loved the home and location, as it was close to all the Disney Parks and many popular restaurants. Working with Troy was smooth and he is a great communicator! Booking, check-in, our time in the house, and check-out, was seamless and he stayed in touch with me the entire time! Would definitely book again!"
6BR Disney Home with 2 Master Suites, Pool & Hot Tub
Private fenced in Pool - Free wifi - Indian creek 3 miles to Disney
Fridge, microwave, oven, stovetop

Private fenced in Pool - Free wifi - Indian creek 3 miles to Disney

9.8 out of 10, Exceptional, (82)
"Home was clean, lots of notes around for lamps, fans etc. Didnt really cook. Just used house to sleep and shower. Definitely need to bring TP, toiletries abd garbage bags. Only get 1 of each."
Private fenced in Pool - Free wifi - Indian creek 3 miles to Disney
Mickey's 9BR Luxury near DISNEY with Pool, Spa | Free Parking, WiFi, Waterpark
Indoor pool, outdoor pool

Mickey's 9BR Luxury near DISNEY with Pool, Spa | Free Parking, WiFi, Waterpark

9.4 out of 10, Exceptional, (120)
"The house was amazing very spacious beautiful set up. Big kitchen area and beds were very comfortable. We all had an amazing time even though it was a short trip but it was all worth it. The kids really enjoyed their self we didn't want to leave. Since my husband is from Orlando but moved to Tallahassee so when he gets a chance to see his family he does so his sister came to visit us one day we was there and we didn't know we had to add her to the list so all it took was for to message the host...
Mickey's 9BR Luxury near DISNEY with Pool, Spa | Free Parking, WiFi, Waterpark
Near Disney - 2 Master King, Pool, Hot Tub, Games, Deck Overlooking Lake!
A heated pool

Near Disney - 2 Master King, Pool, Hot Tub, Games, Deck Overlooking Lake!

10.0 out of 10, Exceptional, (77)
"This was a beautiful place to stay after long days of training. Very clean and all the necessities we needed. The pool and hot tub were great to come home to and relax in. I would recommend the neighborhood and house to anyone staying in the Orlando area. Was also set up perfect if you bring the kids to Disney. "
Near Disney - 2 Master King, Pool, Hot Tub, Games, Deck Overlooking Lake!
3 Bedrooms/ 3 Bathrooms/ The Hub (3205 TT)
TV

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

10.0 out of 10, Exceptional, (23)
"I was in town for a conference and some extra days with my family. This was a great place to stay and had plenty of space for us all. It was 15-25 minutes with traffic from every park and tourist attraction. The check-in process was super simple. The place is towards the back of the community so it was a bit dark back by the doors if the other neighbors don’t have their outside lights on. But all in all I thought it was a great place to stay. "
The price is CA $147
CA $591 total
includes taxes & fees
Apr 27 - Apr 28
3 Bedrooms/ 3 Bathrooms/ The Hub (3205 TT)
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 Winter Haven

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very good, (1925)
"They were contingent on a timeshare , that I had to pay for but did not attend. "
The price is CA $110
CA $148 total
includes taxes & fees
May 4 - May 5
Vacation Village at Parkway
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, (5330)
"Staff was incredibly nice, communication was easy. Location was great, felt just like home, no concerns with not feeling safe. Will be returning in the future! "
The price is CA $127
CA $188 total
includes taxes & fees
May 4 - May 5
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, (1331)
"Clean, comfortable"
Margaritaville Cottages Orlando with H2O Waterpark by Rentyl
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.