Vacation Rentals in Winter Haven, FL

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.
Elegant Winter Haven Villa w/ Dock & Lanai!
10

Excellent

·
Haven Shores
·
4 br
·
Sleeps 8
·
Dishwasher · Beach · Microwave ·
From
$325/night
Check availability
Property
House · 4 Beds · 5 baths
Amenities
Dishwasher
Beach
Microwave
Private Pool
Assigned Parking
Waterfront
Swimming Pool
On Site Laundry
Other spaces
Workspace, Balcony, Garden, Kitchen
Star Wars Theme
10

Excellent

·
Winter Haven
·
5 br
·
Sleeps 15
·
Air Conditioning · Furnished · Dishwasher ·
From
$211/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Air Conditioning
Furnished
Dishwasher
On Site Laundry
Oven
Hot Tub
Wifi
Other spaces
Kitchen
Price drop
Lakefront house for rent
10

Excellent

·
Winter Haven
·
3 br
·
Sleeps 4
·
Waterfront · Wifi · Air Conditioning ·
From
$175/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Waterfront
Wifi
Air Conditioning
Dishwasher
Carpet
Furnished
Lake
On Site Laundry
Other spaces
Kitchen
Price drop
Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun
10

Excellent

·
Winter Haven
·
5 br
·
Sleeps 11
·
Dishwasher · Outdoor Space · Wifi ·
From
$291/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Dishwasher
Wifi
Oven
Air Conditioning
Onsite Management
Waterfront
Lake
On Site Laundry
Other spaces
Workspace, Kitchen
Price drop
Luxury Lakefront Oasis | Heated Pool, Dock & Kayaks | Home Theatre & EV Charger | Near Theme Parks
10

Excellent

·
Winter Haven
·
3 br
·
Sleeps 6
·
Furnished · Residents Lounge · Dishwasher ·
From
$199/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Furnished
Residents Lounge
Dishwasher
Private Pool
Wifi
Air Conditioning
Lake
Swimming Pool
Other spaces
Workspace, Kitchen
Price drop
Lake life living 45 mins from most central FL theme parks...
10

Excellent

·
Tranquility Park
·
3 br
·
Sleeps 8
·
Private Pool · Swimming Pool · Kitchen ·
From
$225/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Private Pool
Swimming Pool
On Site Laundry
Pool
Furnished
Oven
Wifi
Lake
Other spaces
Kitchen

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.
Price drop
Spacious 4-bedroom 2-bath Abode
9.5

Excellent

·
Winter Haven
·
4 br
·
Sleeps 8
·
Workspace · Kitchen · On Site Laundry ·
From
$460/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
On Site Laundry
Fireplace
Furnished
Wifi
Oven
Air Conditioning
Assigned Parking
Dishwasher
Other spaces
Workspace, Kitchen
Price drop
Staybridge Suites Winter Haven - Auburndale

No rating

·
Winter Haven
·
Studio
·
Sleeps 6
·
Furnished ·
From
$195/night
Check availability
Property
Hotel · Studio
Amenities
Furnished
Palm Frond Place

No rating

·
Winter Haven
·
3 br
·
Sleeps 6
·
Pool · Kitchen · Oven ·
From
$157/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Pool
Oven
Air Conditioning
Furnished
Fitness Center
Dishwasher
On Site Laundry
Wifi
Other spaces
Kitchen
Lovely Lakefront Home w/ Grill: 7 Mi to Legoland!
7.8

Very good

·
Winter Haven
·
3 br
·
Sleeps 8
·
Garden · Residents Lounge · Toiletries ·
From
$125/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Residents Lounge
Toiletries
Cable
Central Heat
On Site Laundry
Air Conditioning
Wifi
Dishwasher
Other spaces
Garden, Kitchen, Workspace

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 $51. 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
$51/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
4.5

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
The Russell Lake House

No rating

·
Winter Haven
·
1 br
·
Sleeps 4
·
Private Pool · On Site Laundry · Waterfront ·
From
$65/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Private Pool
On Site Laundry
Waterfront
Furnished
Lake
Wheelchair Accessible
Wifi
Swimming Pool
Lake Ida Beach Resort
7.5

Very good

·
Winter Haven
·
1 br
·
Sleeps 4
·
Furnished · Carpet · Pool ·
From
$69/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Carpet
Pool
Swimming Pool
On Site Laundry
Wifi
Free Parking
Smoking Allowed
Other spaces
Workspace, Kitchen
Winter Haven Abode Near Lakes & Attractions
9.8

Excellent

·
Winter Haven
·
2 br
·
Sleeps 7
·
Wifi · Tv · Air Conditioning ·
From
$70/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Wifi
Tv
Air Conditioning
Oven
Toiletries
Central Heat
Ceiling Fan
Assigned Parking
Other spaces
Kitchen
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
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Updated: September 25, 2023