Vacation Rentals in Winter Haven, FL

Compare 11 vacation rentals and Airbnbs in Winter Haven, FL, from budget stays near Legoland to lakeside homes with pools. Check prices and ratings before booking

Check-in
Tue, 10 Nov
Check-out
Wed, 11 Nov
Rooms and Guests2 Guests, 1 room
Check-in
Tue, 10 Nov
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Check-out
Wed, 11 Nov
Rooms and Guests2 Guests, 1 room
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Check-in
Tue, 10 Nov
-
Check-out
Wed, 11 Nov
Rooms and Guests2 Guests, 1 room
1Filter & Sort
View map
View map
1-11 out of 11
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
5.0
Needs improvement
4 adults
1 bedroom
1 bed
Map
3.3 mi from City Center641 yd from LEGOLAND Florida Resort
Outdoor PoolIndoor PoolFitness Center
  • Indoor and outdoor pools
  • Jacuzzi in guest rooms
  • On-site fitness center
FromUS$ 42 /nightSelect
8.5
Great
Map
1.9 mi from City Center1.1 mi from Rotary Park
Washer/DryerPrivate ParkingKitchenette
  • Private entrance & washer/dryer
  • Fully equipped kitchenette
  • Pets allowed
FromUS$ 81 /nightSelect
7.4
Very good
Map
3.3 mi from City Center2.2 mi from Sertoma Park
Pool TableKids PoolMini Golf
  • Proximity to Legoland park
  • Indoor play area and pool table
  • Kids pool and outdoor swimming
FromUS$ 233 /nightSelect
7.9
Very good
Map
1.0 mi from City Center1121 yd from Rotary Park
Full KitchenWasher Dryer3 Bedrooms
  • Full kitchen with cookware and utensils
  • In-unit washer and dryer
  • Three bedrooms for larger groups
Select
9.6
Perfect
Map
1108 yd from City Center510 yd from Winter Haven Mall
Private ParkingKitchenetteLuggage Storage
  • Private entrance studio apartment
  • Near Legoland Florida attraction
  • Fully equipped kitchenette
FromUS$ 88 /nightSelect
9.8
Perfect
Map
1.2 mi from City Center
Lake viewsOutdoor diningFull kitchen
  • Lake-view patio with outdoor dining
  • Spacious 3-bedroom holiday home
  • Full kitchen with dishwasher and oven
FromUS$ 155 /nightSelect
Getaway ClubhouseHoliday home
9.4
Perfect
Map
1086 yd from City Center570 yd from Winter Haven Mall
GardenFull KitchenBalcony
  • Spacious holiday home with garden
  • Fully equipped kitchen with dishwasher
  • Balcony access in each unit
Select
9.1
Perfect
Map
5.0 mi from City Center1.0 mi from Willowbrook Golf Course
Golf CoursePlay AreaSun Terrace
  • Golf course available on property
  • VIP check-in and express check-out
  • Children's play area with board games
FromUS$ 206 /nightSelect
9.1
Perfect
Map
1263 yd from City Center371 yd from Rotary Park
Lake ViewPrivate ParkingFireplace
  • Spacious villa with private lake views
  • 5 bedrooms with seating and fireplace
  • Free private parking on-site
FromUS$ 182 /nightSelect
10.0
Perfect
Map
1.6 mi from City Center1216 yd from Village Square
Lake ViewsPrivate ParkingOutdoor Dining
  • Private lakefront home with porch
  • Spacious 3-bedroom layout
  • Free private parking included
FromUS$ 232 /nightSelect
7.0
Very good
Map
2.2 mi from City Center1.1 mi from Sertoma Park
Private ParkingFlat-screen TVOutdoor Dining
  • Spacious home with 4 bedrooms
  • Fully equipped kitchen with dishwasher
  • Private garden with outdoor dining
FromUS$ 265 /nightSelect

Winter Haven offers a range of vacation rentals suited for families and groups seeking space and privacy. Budget-wise, prices vary widely: expect to find cheap options like Econo Lodge Winter Haven Chain Of Lakes (rated Decent) alongside mid-range picks such as the spacious Spacious 4-Bedroom 2-Bath Abode or family-focused Groovy Funhouse Getaway - 4 Bdrm Near Legoland with a year-round outdoor pool and an indoor play area. For a quiet retreat, Peaceful Lakeside Retreat (Exceptional, 98/100) has a spa bath and lake views, while Lakeside Lofts At Lake Martha (Superb, 91/100) places you less than 1 km from Garden Ballroom. Most properties include free WiFi, free parking, and full kitchens, making them practical for longer stays.

For the best convenience, look near Chain Of Lakes Park or Legoland Florida, both easily accessible from central rentals like Unique Cozy Studio (Exceptional, 97/100) or Getaway Clubhouse (Superb, 94/100). Serene Lakeside Cottage Retreat and Cozy Cove Stay also offer quiet settings with outdoor spaces and patios. If you need proximity to Winter Haven Hospital, Central Private King Suit Washer Dryer 2 Miles To Hospital provides a practical base. Whether staying for a weekend or a week, these vacation rentals give you the comforts of home with direct access to local lakes and parks.