Winter Haven Vacation Rentals

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Vacation Rentals in Winter Haven

BlockHaven near Legoland & Disney

3.5 star property
$228 nightly
The price is $256
Jul 22 - Jul 23
Total includes taxes and fees
BlockHaven near Legoland & Disney

Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

2.0 star property
9.6 out of 10, Exceptional, (5)
"Great location, clean and great communication with hosts "
$282 nightly
The price is $310
Jul 15 - Jul 16
Total includes taxes and fees
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

The Old Haven - An Enduring Piece of Nostalgia

2.0 star property
9.6 out of 10, Exceptional, (5)
"This home is clean and comfortable. It is perfect for larger groups and walking distance to several waterfront restaurants and public boat docks."
$271 nightly
The price is $297
Jul 19 - Jul 20
Total includes taxes and fees
The Old Haven - An Enduring Piece of Nostalgia

Private/Spacious 1BR Central Near LegoLand 2 Miles

9.8 out of 10, Exceptional, (6)
"Perfect little spot my family and I stayed for 3 nights. "
$165 nightly
The price is $182
Jul 16 - Jul 17
Total includes taxes and fees
Private/Spacious 1BR Central Near LegoLand 2 Miles

Summer Specials! Perfect Couple Oasis! Pet Friendly, 2 Beds

2.0 star property
10.0 out of 10, Exceptional, (1)
"Everything was spotless, fresh,bright and cheerful. Perfect yard for dog ! "
$209 nightly
The price is $231
Jul 16 - Jul 17
Total includes taxes and fees
Summer Specials! Perfect Couple Oasis! Pet Friendly, 2 Beds

Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nice place very convenient for us. Would stay again"
$265 nightly
The price is $291
Aug 3 - Aug 4
Total includes taxes and fees
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

Peaceful Lakeside Retreat

9.8 out of 10, Exceptional, (7)
"House is very spacious (especially the awesome master suite!!) and on a lake with a nice backyard and seating. Large kitchen, living room, dining room and great large sunroom. We thoroughly enjoyed our stay here!"
$346 nightly
The price is $387
Jul 15 - Jul 16
Total includes taxes and fees
Peaceful Lakeside Retreat

Serene, Cozy, Lakefront home

10.0 out of 10, Exceptional, (2)
"2nd time staying here and it does not disappoint. Thank you again for letting us stay in your lovely home "
$300 nightly
The price is $336
Jul 15 - Jul 16
Total includes taxes and fees
Serene, Cozy, Lakefront home

Large 3/1 Near DownTown and Dining

8.4 out of 10, Very Good, (8)
"Clean, quiet and comfortable beds. "
$232 nightly
The price is $256
Jul 17 - Jul 18
Total includes taxes and fees
Large 3/1 Near DownTown and Dining

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

9.6 out of 10, Exceptional, (27)
"The property and owner were terrific. A couple issues were resolved quickly and professionally. "
$348 nightly
The price is $382
Jul 17 - Jul 18
Total includes taxes and fees
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

9.6 out of 10, Exceptional, (61)
"Ideal place to stay next to Legoland. Nicely decorated condo."
$260 nightly
The price is $288
Jul 15 - Jul 16
Total includes taxes and fees
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

$264 nightly
The price is $292
Jul 22 - Jul 23
Total includes taxes and fees
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure

10.0 out of 10, Exceptional, (22)
"Stayed here while in Winterhaven for family funeral. Place was very clean and large enough to accommodate my family. Highly recommended!!"
$406 nightly
The price is $449
Jul 21 - Jul 22
Total includes taxes and fees
Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure

Heated Pool and Hot tub-near Legoland, Disney, Theme parks

9.8 out of 10, Exceptional, (30)
"A clean, spacious home in a quiet cul-de-sac. The host was very easy to work with and would stay again. "
$341 nightly
The price is $377
Jul 15 - Jul 16
Total includes taxes and fees
Heated Pool and Hot tub-near Legoland, Disney, Theme parks

Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

2.0 star property
$345 nightly
The price is $382
Aug 3 - Aug 4
Total includes taxes and fees
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

LEGOLAND! Disney, Universal &+! Your Home Away from Home in Winter Haven, FLA!

9.0 out of 10, Wonderful, (2)
"I'm town for family graduation party. Perfect place to stay"
$400 nightly
The price is $442
Jul 15 - Jul 16
Total includes taxes and fees
LEGOLAND! Disney, Universal &+! Your Home Away from Home in Winter Haven, FLA!

Cheerful New Construction Home

9.0 out of 10, Wonderful, (33)
"A very nice house located extremely close to Legoland. The house kept eight of us with room to spare. Any questions I had for the owner during my stay were answered with almost an immediate response. "
$395 nightly
The price is $437
Jul 15 - Jul 16
Total includes taxes and fees
Cheerful New Construction Home

Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!

9.0 out of 10, Wonderful, (32)
"We loved the lake house. The kids had an awesome time with the tree swings. Thank you for having us!"
$346 nightly
The price is $383
Jul 16 - Jul 17
Total includes taxes and fees
Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!

Charming 3-bedroom house with WiFi and AC in Winter Haven 5Mi Legoland

$183 nightly
The price is $202
Aug 11 - Aug 12
Total includes taxes and fees
Charming 3-bedroom house with WiFi and AC in Winter Haven 5Mi Legoland

Experience family fun! LEGOLAND® Florida just a 12-min drive

9.2 out of 10, Wonderful, (10)
"Clean place, great communication, wonderful stay!"
$376 nightly
The price is $416
Jul 24 - Jul 25
Total includes taxes and fees
Experience family fun! LEGOLAND® Florida just a 12-min drive
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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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 145 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 Peppa Pig Theme Park Florida, 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 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.