Winter Haven Holiday Rentals

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Holiday Rentals in Winter Haven

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 "
The price is AU$478
includes taxes & fees
13 July - 14 July
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown

BlockHaven near Legoland & Disney

3.5 star property
The price is AU$397
includes taxes & fees
22 July - 23 July
BlockHaven near Legoland & Disney

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 "
The price is AU$519
includes taxes & fees
12 July - 13 July
Serene, Cozy, Lakefront home

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."
The price is AU$460
includes taxes & fees
19 July - 20 July
The Old Haven - An Enduring Piece of Nostalgia

Large 3/1 Near DownTown and Dining

8.4 out of 10, Very good, (8)
"Clean, quiet and comfortable beds. "
The price is AU$393
includes taxes & fees
12 July - 13 July
Large 3/1 Near DownTown and Dining

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 ! "
The price is AU$363
includes taxes & fees
13 July - 14 July
Summer Specials! Perfect Couple Oasis! Pet Friendly, 2 Beds

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. "
The price is AU$282
includes taxes & fees
11 July - 12 July
Private/Spacious 1BR Central Near LegoLand 2 Miles

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"
The price is AU$449
includes taxes & fees
3 Aug - 4 Aug
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn

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

9.4 out of 10, Exceptional, (60)
"Ideal place to stay next to Legoland. Nicely decorated condo."
The price is AU$444
includes taxes & fees
13 July - 14 July
*3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724

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!"
The price is AU$610
includes taxes & fees
13 July - 14 July
Peaceful Lakeside Retreat

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

9.8 out of 10, Exceptional, (30)
"Very nice property. Would book here again!"
The price is AU$582
includes taxes & fees
15 July - 16 July
Heated Pool and Hot tub-near Legoland, Disney, Theme parks

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

The price is AU$450
includes taxes & fees
24 July - 25 July
BlockHaven near Legoland, Disney, Universal Studios, Busch Gardens & SeaWorld !!

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"
The price is AU$684
includes taxes & fees
12 July - 13 July
LEGOLAND! Disney, Universal &+! Your Home Away from Home in Winter Haven, FLA!

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!!"
The price is AU$694
includes taxes & fees
21 July - 22 July
Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure

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. "
The price is AU$675
includes taxes & fees
11 July - 12 July
Cheerful New Construction Home

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. "
The price is AU$591
includes taxes & fees
17 July - 18 July
Hook, Line & Leisure: Lakefront Gem, 2 Mi to Dtwn

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

2.0 star property
The price is AU$588
includes taxes & fees
3 Aug - 4 Aug
Live Oak Oasis - Getaway Close to Legoland! Sleeps 8 Guests, Fenced yard, Games

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!"
The price is AU$592
includes taxes & fees
16 July - 17 July
Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!

Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

The price is AU$391
includes taxes & fees
22 July - 23 July
Charming 3-bedroom 2 bathroom home in brilliant Winter Haven,pet friendly, WiFi

Adult-Only Love Hotel with Mermaid Pool

10.0 out of 10, Exceptional, (1)
"This is a true hidden gem. My partner and I were looking for a sexy place with a hot tub and pool.The sleek design across the home gave many exciting tones. The cleaniness and extra supplies with welcome letter provided the right amount of comfort from the hosts right off the bat. This is a must visit. The mermaid pool was a very neat touch! We highly recommended! the hosts. Very welcoming! "
The price is AU$580
includes taxes & fees
14 July - 15 July
Adult-Only Love Hotel with Mermaid Pool
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 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.

What are some of the best holiday rentals that Winter Haven has to offer?

The Berkley, Orlando: This holiday home rental outside of Winter Haven offers a furnished patio, a terrace and a BBQ 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 holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Winter Haven?

Choose from 145 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.