Winter Haven Holiday 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

Holiday Rentals in Winter Haven

Interior
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
10.0 out of 10, Exceptional, (11)
"The house was the perfect size and those beds. So comfy. The house is older but well maintained. Great communication with the host. We really felt safe and relaxed while we were there. Thank you again!!!"
Home w/ Pool, Hot Tub & Game Room, 6 Mi to Disney!
Fridge, microwave, oven, stovetop
⭐⭐⭐⭐⭐Expansive family-friendly vacation home, themed rooms, water park, fitness
10.0 out of 10, Exceptional, (1)
"The home is wonderfully and creatively decorated. The kitchen. dining. tv.pool table area is great fun for being together. We had rain on our visit but the home is conducive to handle all of that. Great visit, wonderfully responsive manager. Thank you"
⭐⭐⭐⭐⭐Expansive family-friendly vacation home, themed rooms, water park, fitness
A heated pool
🌟DISCOUNT NIGHTS AVAILABLE,PRIME LOCATION🌟. Near DISNEY. All-Inclusive 3BR/3BA
10.0 out of 10, Exceptional, (221)
"Had a great time at this property, it was very clean, location within the resort was great and the resort itself felt very safe. Pool area was fun for adults and kids, the bar was nice and all the staff was super friendly! Had a couple questions for the hosts, they were quick to respond and everything was very easy as far as logistics go!"
🌟DISCOUNT NIGHTS AVAILABLE,PRIME LOCATION🌟. Near DISNEY. All-Inclusive 3BR/3BA
Save an average of 15% on thousands of hotels when you're signed in
Indoor pool, outdoor pool
VERY CLOSE TO DISNEY! Fabulous 5 bed Home! Sleeps 11 Pool, Spa, Theater, Gated
10.0 out of 10, Exceptional, (35)
"We had a great stay at this property! It is very conveniently located close to all the Walt Disney World Parks. It was healing to use the jacuzzi and pool after a long day of walking at the Disney parks! The kids enjoyed the themed bedrooms, home theater, pool, popcorn, and the Pacman arcade. Highly recommend it, and I'd choose to stay here again on our next Disney-parks vacation."
VERY CLOSE TO DISNEY! Fabulous 5 bed Home! Sleeps 11 Pool, Spa, Theater, Gated
Fridge, microwave, oven, stovetop
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
9.8 out of 10, Exceptional, (10)
"We come every year for the cheerleading tournament, very safe, gated neighborhood, very responsive owner for any issues, and the only house in the last 6 years where the a/c was actually cold the entire stay!!!"
Champions Gate!*Disney Themes!*4 Bedrooms!*Private Pool!*
Outdoor pool, a heated pool
Smart TV—2 King Beds—Walt Disney World—Resort—Parking—private pool—full kitchen
9.8 out of 10, Exceptional, (27)
"Excellent home, good pool , excellent neighborhood. I love this house , just need more good cleaner."
The price is NZ$705
includes taxes & fees
16 Jun - 17 Jun
Smart TV—2 King Beds—Walt Disney World—Resort—Parking—private pool—full kitchen
Pool
Brand New Luxury Villa! Dog Friendly, Gated Resort w/ tons of Amenities, Jacuzzi, Free Wifi, BBQ Grill!
9.6 out of 10, Exceptional, (5)
"House was beautiful, everything was great!"
Brand New Luxury Villa! Dog Friendly, Gated Resort w/ tons of Amenities, Jacuzzi, Free Wifi, BBQ Grill!
Lobby sitting area
The Berkley, Orlando
4.0 star property
9.4 out of 10, Exceptional, (1413)
"Amazing 4 bedroom condo loved everything about the place "
The Berkley, Orlando
Fridge, microwave, oven, stovetop
Stylish retreat with a private, heated pool, central AC, & garage game room
9.4 out of 10, Exceptional, (16)
"Very relaxing to have a home to go to after a busy day. Some minor things needed attention. Overall it was great. I would give it a 4.5 out of 5."
Stylish retreat with a private, heated pool, central AC, & garage game room
Outdoor pool, pool loungers, lifeguards on site
Spectrum Resort Orlando
4.0 star property
9.2 out of 10, Wonderful, (191)
"Loved the place. Wished the pool was open longer. "
Spectrum Resort Orlando
Outdoor pool, pool umbrellas, pool loungers
Magic Village Yards, Trademark Collection by Wyndham
4.0 star property
9.2 out of 10, Wonderful, (1068)
"We stayed here because it is close to all the parks. Pleasantly surprised with the unit too. All new!"
Magic Village Yards, Trademark Collection by Wyndham
Terrace/patio
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
9.2 out of 10, Wonderful, (12)
"Wonderful place to stay. Excellent communication. Very accommodating to our requests. We enjoyed our stay. Thank you"
Family house / 4 BD-2Baths (August promotion!! low rates for this month)
Private kitchen
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!
9.2 out of 10, Wonderful, (96)
"We had a wonderful stay, and the host is very responsive and helpful. Great location close to Disney"
THE ULTIMATE MOUSE HOUSE, a Spectacular Disney Themed Pool Villa for Families!!
Lake
Lifetime of Vacations Resort
3.0 star property
9.0 out of 10, Wonderful, (82)
"Place is good Its a older place but its safe and in a great location. Staff is very nice and area is a hub for Disneyland merchandise. "
Lifetime of Vacations Resort
A heated pool
Luxury 4 bedroom 3 bath pool Home 283
9.0 out of 10, Wonderful, (12)
"Truly a Great Experience! Visited family In Kissimmee and our first time in an AirB&B. House was immaculate and furnished with everything we needed to enjoy ourselves. I had a question about the keypad code, I emailed at about 10:30 pm and the response was immediate. I really appreciated that. We will definitely return again."
Luxury 4 bedroom 3 bath pool Home 283
Outdoor pool, pool umbrellas, pool loungers
Grand Lake Resort
3.0 star property
9.0 out of 10, Wonderful, (85)
"Very courteous staff "
Grand Lake Resort
Interior
Margaritaville Resort Orlando Cottages by Rentyl
4.0 star property
8.8 out of 10, Excellent, (842)
"It was wonderful, clean and very quiet! Perfect staycation "
Margaritaville Resort Orlando Cottages by Rentyl
Waterslide
Reunion Resort & Golf Club
5.0 star property
8.6 out of 10, Excellent, (1120)
"Perfect for the family. "
The price is NZ$530
includes taxes & fees
3 Jun - 4 Jun
Reunion Resort & Golf Club
2 outdoor pools, pool umbrellas, pool loungers
Encantada Resort Vacation Townhomes by IDILIQ
3.0 star property
8.6 out of 10, Excellent, (1253)
"It was great besides no air conditioning upstairs where bedrooms are , even though they clean after you leave there should be a dust pan and mop to do cleaning while there "
The price is NZ$430
includes taxes & fees
11 Jun - 12 Jun
Encantada Resort Vacation Townhomes by IDILIQ
Condo, 2 Bedrooms, Hot Tub, Garden View (Standard Bahama Bay San Salvador Vill) | Property grounds
Bahama Bay Resort
3.5 star property
8.6 out of 10, Excellent, (2024)
"We had a lower end 2 bedroom unit. Very spacious & updated nicely. We will definitely return to this resort. "
Bahama Bay Resort
Don't see what you're looking for?
See all available properties in Winter Haven
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.

Other types of properties in Winter Haven you may be interested in

Standard Room, 2 Queen Beds, Non Smoking, Bathtub (Larger Room)
Best Western Plus Winter Haven Inn & Suites 
2.5 star property
9.4 out of 10, Exceptional, (342)
"Nice clean hotel. Breakfast could’ve been better. "
The price is NZ$206
includes taxes & fees
23 May - 24 May
Best Western Plus Winter Haven Inn & Suites 
Bar (on property)
Holiday Inn Winter Haven, an IHG Hotel
3.0 star property
8.8 out of 10, Excellent, (954)
"There are holes punched into the bathroom door. The pool has been shut down so we had to walk over to the other hotels pool. Not a huge deal but inconvenient. "
The price is NZ$174
includes taxes & fees
11 Jun - 12 Jun
Holiday Inn Winter Haven, an IHG Hotel
3 outdoor pools, a heated pool, pool cabanas (surcharge), pool umbrellas
The Grove Resort & Water Park Orlando
4.0 star property
8.2 out of 10, Very good, (5407)
"Everything was perfect. The early morning park maintenance was pretty loud, overall a really fun family vacation. Will definitely be back "
The price is NZ$447
includes taxes & fees
23 May - 24 May
The Grove Resort & Water Park 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winter Haven holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winter Haven. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winter Haven. Seeing all the best attractions is bound to make you fall in love with Winter Haven. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winter Haven short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Winter Haven?

Yes, there are holiday rentals in Winter Haven close to LEGOLAND® Florida, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Winter Haven speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave time to check out the gardens and entertainment venues during your visit.

How many holiday rentals are there in Winter Haven?

Choose from 102 Expedia holiday rentals in Winter Haven for a memorable holiday.

What can I see and do in Winter Haven?

Family-friendly attractions include LEGOLAND® Florida and Indigo's Family Fun Center, whereas The Circle B Bar Reserve and Rotary Park are a couple of great spots to enjoy the outdoors. Theatre Winter Haven and Chain of Lakes Park are other places to visit while you're in town.

What are holiday rentals like in Winter Haven?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winter Haven. Holiday rentals offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.

Recent reviews of Winter Haven properties
Expedia verified reviews