Winter Haven Vacation Rentals

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Our top choices for Winter Haven vacation rentals

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn
3.0 star property
Winter Haven
10.0 out of 10, Exceptional, (3 reviews)
"We stayed here because our soccer team had a tournament in the area. We had a couple families stay and the price was much cheaper than hotels around the area. The house is beautiful and spacious inside. Has alot of upgrades. At first we thought the neighborhood looked a little off, but we had no issues at all with our stay. We have some other tournaments in this area later in the year and we will definitely be booking to stay here again."
United States
John
The price is CA $233
CA $597 total
includes taxes & fees
Feb 15 - Feb 16
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (1 review)
"House was great, perfect central location. Very quiet neighborhood nice farm outside peaceful back yard seating area. "
United States
Wade
The price is CA $104
CA $365 total
includes taxes & fees
Mar 1 - Mar 2
BlockHaven near Legoland & Disney

Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (188 reviews)
"We have stayed here several times. "
United States
Martha
The price is CA $98
CA $110 total
includes taxes & fees
Feb 25 - Feb 26
Lake Ida Beach Resort

voco Kissimmee Orlando by IHG

voco Kissimmee Orlando by IHG
4.0 star property
Kissimmee
7.6 out of 10, Good, (1,007 reviews)
"Staff was very helpful, location was what we needed and rooms and pool were outstanding "
United States
Chester Joseph
The price is CA $101
CA $145 total
includes taxes & fees
Feb 23 - Feb 24
voco Kissimmee Orlando by IHG

Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (197 reviews)
"Nice rooms helpful staff would go again for sure"
United States
David
Camp Mack Lodge, Marina & RV Resort

Oasis Private Ensuite Room Shared Home

Oasis Private Ensuite Room Shared Home
3.5 star property
Kissimmee
The price is CA $80
CA $192 total
includes taxes & fees
Feb 23 - Feb 24
Oasis Private Ensuite Room Shared Home

Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration
3.0 star property
Kissimmee
8.6 out of 10, Excellent, (3,338 reviews)
"Yes .. very clean rooms and hotel chef was great"
United States
Alicia
The price is CA $116
CA $165 total
includes taxes & fees
Mar 8 - Mar 9
Vacation Village Orlando, Celebration

Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse

Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse
3.5 star property
Kissimmee
The price is CA $213
CA $862 total
includes taxes & fees
Feb 16 - Feb 17
Serene Stay At Terra Verde Resort By Shine Villas 111 3 Bedroom Townhouse

Leisure Lounge

Leisure Lounge
3.5 star property
Solterra Resort
8.4 out of 10, Very good, (17 reviews)
"The room was so nice! Very clean and in tact."
United States
Amber Carchelle
The price is CA $59
CA $158 total
includes taxes & fees
Feb 18 - Feb 19
Leisure Lounge

Barefoot'n Resort Kissimmee Orlando

Barefoot'n Resort Kissimmee Orlando
2.5 star property
Kissimmee
9.0 out of 10, Wonderful, (202 reviews)
"Great place. Great location. "
United States
Andrew
The price is CA $145
CA $182 total
includes taxes & fees
Feb 26 - Feb 27
Barefoot'n Resort Kissimmee Orlando

Mickey s Villa - Child-friendly Game Room Pool Spa

Mickey s Villa - Child-friendly Game Room Pool Spa
2.0 star property
Kissimmee
The price is CA $197
CA $723 total
includes taxes & fees
Feb 23 - Feb 24
Mickey s Villa - Child-friendly Game Room Pool Spa

Barefoot Suites

Barefoot Suites
3.0 star property
Kissimmee
9.0 out of 10, Wonderful, (1,824 reviews)
"Great place. To stay "
United States
THOMAS
The price is CA $105
CA $137 total
includes taxes & fees
Mar 8 - Mar 9
Barefoot Suites

Magical Dreams

Magical Dreams
4.0 star property
Kissimmee
5.4 out of 10, (16 reviews)
"Overall was a good stay . "
United States
Sorina
The price is CA $91
CA $197 total
includes taxes & fees
Feb 18 - Feb 19
Magical Dreams

Elita Inn

Elita Inn
3.0 star property
Dundee
7.6 out of 10, Good, (25 reviews)
"Very nice accommadations..friendly staff"
United States
lance
The price is CA $107
CA $120 total
includes taxes & fees
Mar 16 - Mar 17
Elita Inn

Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Holiday Inn Club Vacations Orlando Breeze Resort by IHG
3.5 star property
Davenport
9.2 out of 10, Wonderful, (529 reviews)
"It was lovely! We would stay here again for sure! "
United States
Hilary
The price is CA $170
CA $215 total
includes taxes & fees
Feb 24 - Feb 25
Holiday Inn Club Vacations Orlando Breeze Resort by IHG

Jade Manor

Jade Manor
2.5 star property
Solterra Resort
8.8 out of 10, Excellent, (3 reviews)
"Amazing "
United States
Nilda
The price is CA $74
CA $174 total
includes taxes & fees
Feb 25 - Feb 26
Jade Manor

Regal Oaks Resort Vacation Townhomes by IDILIQ

Regal Oaks Resort Vacation Townhomes by IDILIQ
4.0 star property
Kissimmee
8.4 out of 10, Very good, (3,063 reviews)
"Overall the stay was great. Staff were very helpful. We had some issues with the room carpet but it was taken care of as soon as I reported to the front desk. I very much recommend this place."
United States
Lucia
Regal Oaks Resort Vacation Townhomes by IDILIQ

Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse

Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse
3.0 star property
Loughman
The price is CA $194
CA $1,144 total
includes taxes & fees
Feb 16 - Feb 17
Harmony Haven Boutique Townhome At Azzure Resort Near Disney By Shine Villas 6 Bedroom Townhouse

FL- 1904 Nice Ct

FL- 1904 Nice Ct
3.0 star property
Kissimmee
The price is CA $252
CA $694 total
includes taxes & fees
Feb 16 - Feb 17
FL- 1904 Nice Ct

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes

Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
3.0 star property
Kissimmee
The price is CA $186
CA $373 total
includes taxes & fees
Feb 22 - Feb 23
Adeline Apartments 15m to Parks, Pet Friendly, Free Parking by Heavenly Homes
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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Top Winter Haven Hotel Reviews

Find out more about Winter Haven

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Winter Haven?

Yes, there are vacation rentals in Winter Haven close to LEGOLAND® Florida, or you can choose a more secluded option if you'd like a relaxing place to 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.

What's the top vacation rental that Winter Haven has to offer?

The Berkley, Orlando: This vacation home rental outside of Winter Haven offers a furnished patio, a terrace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave, and a coffee maker. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Winter Haven?

Choose from 66 Expedia vacation rentals in Winter Haven for a memorable vacation.

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 Inman 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 vacation rentals like in Winter Haven?

Vacation rentals are private properties you can book for a few days or a quick weekend in Winter Haven. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.