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, (1608)
"I enjoyed my stay at The Berkeley Orlando property.....the unit's interior was really nice, quiet and spacious. The front desk agent that checked me in was polite and very professional. I will definitely stay there again. "
The Berkley, Orlando

Free Water Park! Private Pool & Game Room (7739)

8.2 out of 10, Very good, (57)
"Will stay again"
Free Water Park! Private Pool & Game Room (7739)

Formosa Valley Resort by UNE Homes

4.0 star property
9.4 out of 10, Exceptional, (128)
"The place is beautiful, clean and Romy for a big family"
Formosa Valley Resort by UNE Homes

Encore Resort

4.0 star property
6.4 out of 10, (113)
"It was a very nice home. My family had a great time"
Encore Resort

The Bear's Den Resort Orlando

5.0 star property
7.6 out of 10, Good, (20)
"Check-in and check-out were easy. The staff was very accommodating. The home is stunningly beautiful and clean. We loved every moment of our stay and will return!"
The Bear's Den Resort Orlando

POOL HOME - Luxury Windsor Palms Resort - 6 miles to Disney! POOL HEAT INCLUDED!

10.0 out of 10, Exceptional, (142)
"Our stay was perfect. The home has everything you need and is close to the parks. This was our 2nd stay with host Elaine. She is great to work with and we are planning next stay this spring! "
POOL HOME - Luxury Windsor Palms Resort - 6 miles to Disney! POOL HEAT INCLUDED!

Lake View! Free Waterpark! Modern 5BR- Windsor at Westside (8890GC)

7.6 out of 10, Good, (42)
"The place was nice. My friends and I enjoyed our stay. The only cons I have are the carpets (stained…feels unclean), the peeling leather (white) couch, and the mesh screening above the pools needs to get fixed (there’s a big hole). Other than that, we really enjoyed our stay. Check in/check out process was really easy and no complications. Please read before booking, if I had a chance review the Renter’s Agreement before booking, that would’ve been helpful in deciding to book this place or...
Lake View! Free Waterpark! Modern 5BR- Windsor at Westside (8890GC)

Next to Disney Properties! PoolSpa Vacation Home Super Convenient Location

9.8 out of 10, Exceptional, (8)
"Easy checkin process. Owner was great with communication, prompt, friendly and very helpful. He even let us extend our check out time. Lovely neighborhood and very spacious villa. "
Next to Disney Properties! PoolSpa Vacation Home Super Convenient Location

Great 3 bed/3 bath townhome in Crestwynd Bay, just 2 miles from WDW main gate

9.2 out of 10, Wonderful, (104)
"Our stay was very nice and the neighborhood was always quiet. We didn't take advantage of the neighborhood amenities but we all slept very well and the showers were great too with nice water pressure and temperature changes. Great experience overall!"
Great 3 bed/3 bath townhome in Crestwynd Bay, just 2 miles from WDW main gate

Amazing-Movie Theater-Private Pool/Spa-Great View-Themed Bedrooms

9.8 out of 10, Exceptional, (92)
"Our family enjoyed our Thanksgiving week at the house. We celebrated birthdays and our grandkids first trip to Disney. We paid the extra fee for the heated pool and bbq and thoroughly enjoyed both. The theater room was enjoyable and our grandkids especially enjoyed the community pool water slides. There was plenty of room for all 8 of us. We definitely would stay here again when coming to Orlando."
Amazing-Movie Theater-Private Pool/Spa-Great View-Themed Bedrooms

NEW Luxury Villa Near Disney w/ Pool & Spa!

9.8 out of 10, Exceptional, (40)
"Loved staying here! Great place to stay if you are visiting Disney!!! The rooms are all SO CUTE!"
NEW Luxury Villa Near Disney w/ Pool & Spa!

Caribbean Dreamin | Vibrant Margaritaville Resort

9.8 out of 10, Exceptional, (9)
"The property was not just clean. It was move in ready clean. Everything was well planned and thought out. There was even an umbrella we could use for the afternoon showers. We really enjoyed our stay and there was tons to do nearby. It was a very quiet and relaxing place to stay at!!"
Caribbean Dreamin | Vibrant Margaritaville Resort

Brand New, Completely Renovated, South Facing w/ Luxurious Finishes & Updates

9.2 out of 10, Wonderful, (61)
"The condo was very nicely decorated and had all of the things we needed for our 5 day stay. Communication with the property owner/manager was prompt and very easy. The only things negative we have to say about the property are as follows: Shower heads were not sufficient for gals with thick curly hair. Some hand held shower heads might be a nice addition….at least one anyway. And sometimes there was no hot water in the kitchen sink. Two of the mattresses were very firm which might be ok for some...
Brand New, Completely Renovated, South Facing w/ Luxurious Finishes & Updates

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

9.0 out of 10, Wonderful, (63)
"Is nice and clean i love the place"
MO800 Champions Gate 5 Bedroom bathroom 5 Private Pool & Jaccuzi, Free Waterpark

Great Vacation Home Ideal Retreat in the Heart of the Disney area

9.6 out of 10, Exceptional, (164)
"Excellent overall will be staying again and again"
Great Vacation Home Ideal Retreat in the Heart of the Disney area

6 Bed, 4 Bath, Private Pool, Hot tub, Gated entry near Theme Parks

9.6 out of 10, Exceptional, (18)
"Only issue we had was none of the outlets worked in the pool area. And pool guy came when we were just going in pool. No notice. Just walked in when we were there. Would have been nice to be given a heads up. Also every timer we turned ac down it jumped right back up. House was warm. "
6 Bed, 4 Bath, Private Pool, Hot tub, Gated entry near Theme Parks

Dog-friendly townhome w/ private pool & resort water park - close to Disney

8.0 out of 10, Very good, (45)
"Everything was good pool had"
Dog-friendly townhome w/ private pool & resort water park - close to Disney

Villa The Dreamers , ultra modern villa , 3 miles from Disney , pool

9.6 out of 10, Exceptional, (169)
"The house was overall nice. Pros: large with lots of space and cute Disney decorations. Cons: we have 4 kids and after having a pool day there at the house, every single one of them came out of the pool with blisters on their hands and feet, 2/4 were bleeding on toes, we think it was a combination of too much chlorine and rough pool bottom. Dish washer didn’t work properly, and beds weren’t the most comfy, we went to Walmart and bought a mattress topper. But overall it was a nice stay!"
Villa The Dreamers , ultra modern villa , 3 miles from Disney , pool

Sophisticated 4 En Suites w/ Private Hot Tub

9.8 out of 10, Exceptional, (9)
"Everything was as advertised. Place was very clean and modern. Very nice accommodations. Would definitely stay there again."
Sophisticated 4 En Suites w/ Private Hot Tub

Family Villa Near Disney| Pool| Spa| Theater|Games

10.0 out of 10, Exceptional, (14)
"Property was exactly as described, perfect place to stay and so close to Disney. This house was amazing inside as well as the outside area. We will definitely return to stay on our next family vacation!"
Family Villa Near Disney| Pool| Spa| Theater|Games
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

Seralago Hotel & Suites Main Gate East

3.0 star property
5.2 out of 10, (5588)
"Women at the front are not approachable, more on the rude side. They completely ignore you until you say excuse me. Besides that everything and everyone else was very helpful and pleasant. "
The price is CA $54
CA $90 total
includes taxes & fees
Dec 9 - Dec 10
Seralago Hotel & Suites Main Gate East

Summer Bay Orlando by Exploria Resorts

3.5 star property
8.4 out of 10, Very good, (5032)
"Love this place"
The price is CA $177
CA $244 total
includes taxes & fees
Dec 18 - Dec 19
Summer Bay Orlando by Exploria Resorts

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1094)
"Great location "
Margaritaville Resort Orlando Cottages 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.