Vacation Rentals in Winter Haven, FL

118 rentals

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Winter Haven, FL

Book a vacation rental in Winter Haven that has the highest visitor rating. Here are 6 of the best vacation rentals in Winter Haven.
Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun
10

Excellent

·
Winter Haven
·
5 br
·
Sleeps 11
·
Lake · Outdoor Space · Wifi ·
From
$402/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Lake
Wifi
Oven
Dishwasher
Onsite Management
Furnished
Waterfront
Air Conditioning
Other spaces
Outdoor Space, Workspace, Kitchen
Winter Haven Apt: 1 Mi to Polk State College!
10

Excellent

·
Winter Haven
·
1 br
·
Sleeps 2
·
Workspace · Wifi · Furnished ·
From
$94/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Furnished
Air Conditioning
Assigned Parking
Oven
Central Heat
Other spaces
Workspace, Kitchen, Balcony
Lake life living 45 mins from most central FL theme parks...
10

Excellent

·
Tranquility Park
·
3 br
·
Sleeps 8
·
Lake · Swimming Pool · Kitchen ·
From
$221/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Lake
Swimming Pool
Pool
Private Pool
In Unit Laundry
Oven
Wifi
Waterfront
Other spaces
Kitchen
Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!
10

Excellent

·
Winter Haven
·
4 br
·
Sleeps 10
·
Air Conditioning · Waterfront · Workspace ·
From
$388/night
Check availability
Property
House · 4 Beds · 5 baths
Amenities
Air Conditioning
Waterfront
Pool
Furnished
Concierge Service
Dishwasher
Swimming Pool
Wifi
Other spaces
Workspace, Kitchen, Balcony
cozy for the family close to Legoland
10

Excellent

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Winter Haven
·
2 br
·
Sleeps 5
·
Furnished · Kitchen · In Unit Laundry ·
From
$110/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Furnished
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Waterfront Winter Haven Home with Dock & Hot Tub!
10

Excellent

·
Winter Haven
·
4 br
·
Sleeps 12
·
Outdoor Space · Private Pool · Air Conditioning ·
From
$471/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Private Pool
Air Conditioning
Pool
Dishwasher
Swimming Pool
Beach
Central Heat
Lake
Other spaces
Outdoor Space, Kitchen, Workspace

Our Recommended Vacation Rentals in Winter Haven, FL

We analyzed vacation rentals in Winter Haven from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Winter Haven to help you find a deal for your next trip.
Lovely Lakefront Home w/ Grill: 7 Mi to Legoland!
8

Very good

·
Winter Haven
·
3 br
·
Sleeps 8
·
Waterfront · Kitchen · Free Parking ·
From
$125/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Waterfront
Free Parking
Residents Lounge
Central Heat
Ceiling Fan
Fireplace
Microwave
Air Conditioning
Other spaces
Kitchen, Workspace, Garden
Spacious 4-bedroom 2-bath Abode
9.5

Excellent

·
Winter Haven
·
4 br
·
Sleeps 8
·
Workspace · Outdoor Space · Dishwasher ·
From
$294/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Dishwasher
Wifi
Oven
In Unit Laundry
Assigned Parking
Free Parking
Air Conditioning
Fireplace
Other spaces
Workspace, Outdoor Space, Kitchen
Chanti’s Place, Winter Haven. Great Longterm Stay

No rating

·
Winter Haven
·
4 br
·
Sleeps 10
·
Oven · Storage · Air Conditioning ·
From
$110/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Oven
Storage
Air Conditioning
Assigned Parking
On Site Laundry
In Unit Laundry
Dishwasher
Lake
Other spaces
Kitchen, Outdoor Space, Workspace
Yasins Rogue One

No rating

·
Winter Haven
·
5 br
·
Sleeps 14
·
Outdoor Space · Furnished · In Unit Laundry ·
From
$158/night
Check availability
Property
Apartment · 5 Beds · 3 baths
Amenities
Furnished
In Unit Laundry
Waterfront
Hardwood Floor
Assigned Parking
Dishwasher
Lake
Air Conditioning
Other spaces
Outdoor Space, Kitchen, Workspace
Tangerine Daydreams
7

Very good

·
Winter Haven
·
3 br
·
Sleeps 10
·
In Unit Laundry · Oven · Dishwasher ·
From
$167/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
In Unit Laundry
Oven
Dishwasher
Wifi
Assigned Parking
Pool
Furnished
On Site Laundry
Other spaces
Kitchen, Outdoor Space
Spring Break Specials! Pet Friendly, 7 Beds, Family Oasis

No rating

·
Winter Haven
·
4 br
·
Sleeps 9
·
Workspace · Dishwasher · On Site Laundry ·
From
$314/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Dishwasher
On Site Laundry
Free Parking
Waterfront
Oven
Air Conditioning
Hardwood Floor
In Unit Laundry
Other spaces
Workspace, Outdoor Space, Kitchen

Budget-Friendly Vacation Rentals in Winter Haven, FL

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Winter Haven starting at $54. Use the price filter at the top of the page to search for more specific prices.
Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown
10

Excellent

·
Winter Haven
·
1 br
·
Sleeps 2
·
In Unit Laundry · Wifi · Kitchen ·
From
$54/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen, Workspace
Travel Inn Winter Haven
4.2

Good

·
Winter Haven
·
1 br
·
Sleeps 10
·
Assigned Parking · Swimming Pool · Air Conditioning ·
From
$58/night
Check availability
Property
Hotel · 1 Bed
Amenities
Assigned Parking
Swimming Pool
Air Conditioning
Pool
Wifi
Carpet
Furnished
Business Center
Other spaces
Workspace
Budget Inn Winter Haven Auburndale
6.5

Good

·
Winter Haven
·
1 br
·
Sleeps 2
·
Wifi · Air Conditioning · Free Parking ·
From
$61/night
Check availability
Property
Hotel · 1 Bed
Amenities
Wifi
Air Conditioning
Free Parking
Furnished
$2,000 - 2 Bedroom 2 Bathroom Condo In Winter Haven With Great Amenities

No rating

·
Winter Haven
·
2 br
·
High Ceilings · Fireplace · In Unit Laundry ·
From
$67/night
Min stay: 90 nights
Property
Condo · 2 Beds · 2 baths
Amenities
High Ceilings
Fireplace
In Unit Laundry
Air Conditioning
Storage
Swimming Pool
Assigned Parking
Other spaces
Balcony
Winter Haven Abode Near Lakes & Attractions
9.6

Excellent

·
Winter Haven
·
2 br
·
Sleeps 7
·
Toiletries · Kitchen · Central Heat ·
From
$70/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Toiletries
Central Heat
Air Conditioning
Oven
Free Parking
Tv
Ceiling Fan
Assigned Parking
Other spaces
Kitchen, Walk In Closets
Waterfront Vacation Rental on Lake Mirror!

No rating

·
Winter Haven
·
2 br
·
Sleeps 5
·
Garage Parking · Ceiling Fan · Kitchen ·
From
$73/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Garage Parking
Ceiling Fan
Waterfront
In Unit Laundry
Oven
Furnished
Lake
Wifi
Other spaces
Kitchen, Outdoor Space
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Updated: February 26, 2024