411+ Private Villas and Holiday Rentals in Winter Haven |
Winter Haven Holiday Rentals
10.0
Exceptional
(1 Review)
- Lakeland - Winter Haven
- Winter Haven
- 4.16 mi to center
1469 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $297/Night
For 7 Nights CA $2,078
10.0
Exceptional
(5 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 0.53 mi to center
1614.59 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Air Conditioner
CA $258/Night
For 7 Nights CA $1,805
10.0
Exceptional
(3 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.52 mi to center
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $600/Night
For 7 Nights CA $4,202
New
- Lakeland - Winter Haven
- Winter Haven
- 3.62 mi to center
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
CA $271/Night
For 7 Nights CA $1,894
10.0
Exceptional
(5 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.35 mi to center
796.53 ft²
5 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
CA $305/Night
For 7 Nights CA $2,133
10.0
Exceptional
(30 Reviews)
- Lakeland - Winter Haven
- Cypress Gardens
- 1.53 mi to center
600 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $318/Night
For 7 Nights CA $2,226
10.0
Exceptional
(22 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 3.98 mi to center
1279 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
CA $298/Night
For 7 Nights CA $2,083
10.0
Exceptional
(22 Reviews)
- Lakeland - Winter Haven
- Cypress Gardens
- 0.24 mi to center
412 ft²
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $107/Night
For 7 Nights CA $752
10.0
Exceptional
(17 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.10 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $140/Night
For 7 Nights CA $977
Luxury Holiday Rentals in Winter Haven
Over 402+ Luxury Holiday Rentals in or Near Winter Haven
10.0
Exceptional
(4 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.16 mi to center
3582 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $12,632/Night
For 7 Nights CA $88,421
New
1216.32 ft²
12 Guests
2 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
CA $2,568/Night
For 7 Nights CA $17,978
New
1184.03 ft²
10 Guests
3 Bedrooms
1 Bathroom
House
- Fireplace/Heating
- Parking
- Air Conditioner
CA $2,568/Night
For 7 Nights CA $17,978
10.0
Exceptional
(3 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.29 mi to center
2497.23 ft²
17 Guests
4 Bedrooms
3 Bathrooms
Free Cancellation
House
- Hot Tub
- Fireplace/Heating
- Pool
CA $1,602/Night
For 7 Nights CA $11,216
10.0
Exceptional
(1 Review)
- Lakeland - Winter Haven
- Winter Haven
- 1.29 mi to center
2900 ft²
18 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $1,424/Night
For 7 Nights CA $9,969
New
- Lakeland - Winter Haven
- Cypress Gardens
- 0.77 mi to center
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $1,289/Night
For 7 Nights CA $9,020
New
- Lakeland - Winter Haven
- Cypress Gardens
- 0.77 mi to center
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $1,289/Night
For 7 Nights CA $9,020
10.0
Exceptional
(27 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 3.79 mi to center
3000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $1,273/Night
For 7 Nights CA $8,912
New
- Lakeland - Winter Haven
- Cypress Gardens
- 0.77 mi to center
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $1,218/Night
For 7 Nights CA $8,527
Top-Rated Holiday Rentals with a Pool in Winter Haven
Over 151+ The Best Private Villas and Holiday Rentals in Winter Haven with a Pool
10.0
Exceptional
(73 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 4.23 mi to center
1926 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
CA $528/Night
For 7 Nights CA $3,698
10.0
Exceptional
(69 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.66 mi to center
2953 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $597/Night
For 7 Nights CA $4,178
10.0
Exceptional
(52 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 4.36 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $505/Night
For 7 Nights CA $3,534
10.0
Exceptional
(25 Reviews)
- Lakeland - Winter Haven
- Inwood
- 0.92 mi to center
12 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Pool
CA $600/Night
For 7 Nights CA $4,198
10.0
Exceptional
(24 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 0.68 mi to center
11 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
CA $668/Night
For 7 Nights CA $4,674
10.0
Exceptional
(15 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 3.60 mi to center
3045 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $592/Night
For 7 Nights CA $4,142
10.0
Exceptional
(13 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.18 mi to center
4732 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
CA $846/Night
For 7 Nights CA $5,923
10.0
Exceptional
(13 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 2.51 mi to center
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $447/Night
For 7 Nights CA $3,129
10.0
Exceptional
(12 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.34 mi to center
11 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
CA $725/Night
For 7 Nights CA $5,076
Pet-Friendly Holiday Rentals in Winter Haven
Over 113+ Pet-Friendly Holiday Rentals in or Near Winter Haven
10.0
Exceptional
(14 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 0.93 mi to center
540 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $142/Night
For 7 Nights CA $993
10.0
Exceptional
(3 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.35 mi to center
1883.68 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- View
CA $741/Night
For 7 Nights CA $5,187
10.0
Exceptional
(26 Reviews)
- Lakeland - Winter Haven
- Cypress Gardens
- 0.67 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $571/Night
For 7 Nights CA $4,000
10.0
Exceptional
(12 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 3.98 mi to center
1279 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
CA $294/Night
For 7 Nights CA $2,059
10.0
Exceptional
(2 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.35 mi to center
3304.52 ft²
22 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
CA $673/Night
For 7 Nights CA $4,708
10.0
Exceptional
(5 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.35 mi to center
800 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $359/Night
For 7 Nights CA $2,515
10.0
Exceptional
(1 Review)
- Lakeland - Winter Haven
- Winter Haven
- 0.23 mi to center
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $179/Night
For 7 Nights CA $1,253
New
- Lakeland - Winter Haven
- Winter Haven
- 4.13 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
CA $441/Night
For 7 Nights CA $3,086
New
- Lakeland - Winter Haven
- Winter Haven
- 1.22 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
CA $280/Night
For 7 Nights CA $1,961
Large Holiday Rentals and Private Villas in Winter Haven
Over 77+ Large Holiday Rentals and Private Villas in or Near Winter Haven
10.0
Exceptional
(23 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.35 mi to center
1800 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $698/Night
For 7 Nights CA $4,889
10.0
Exceptional
(2 Reviews)
1878.3 ft²
14 Guests
6 Bedrooms
4 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
CA $274/Night
For 7 Nights CA $1,918
10.0
Exceptional
(6 Reviews)
- Lakeland - Winter Haven
- Cypress Gardens
- 1.17 mi to center
10 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
CA $376/Night
For 7 Nights CA $2,633
10.0
Exceptional
(1 Review)
2949.31 ft²
12 Guests
4 Bedrooms
3 Bathrooms
House
- Hot Tub
- Fireplace/Heating
- Pool
CA $431/Night
For 7 Nights CA $3,020
10.0
Exceptional
(4 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 2.20 mi to center
2550 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Kitchen
CA $565/Night
For 7 Nights CA $3,952
10.0
Exceptional
(2 Reviews)
- Lakeland - Winter Haven
- Cypress Gardens
- 0.31 mi to center
1903 ft²
12 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Ocean View
- Balcony/Terrace
- View
CA $499/Night
For 7 Nights CA $3,496
10.0
Exceptional
(2 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 3.32 mi to center
1555 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $467/Night
For 7 Nights CA $3,270
10.0
Exceptional
(2 Reviews)
- Lakeland - Winter Haven
- Cypress Gardens
- 1.35 mi to center
12 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
CA $396/Night
For 7 Nights CA $2,774
10.0
Exceptional
(1 Review)
- Lakeland - Winter Haven
- Jan Phyl Village
- 0.95 mi to center
1800 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $374/Night
For 7 Nights CA $2,619
Wheelchair Accessible Holiday Homes in Winter Haven
Over 26+ Wheelchair Accessible Holiday Homes in or Near Winter Haven
9.2
Exceptional
(11 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.28 mi to center
6060 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $595/Night
For 7 Nights CA $4,161
8.4
Excellent
(1554 Reviews)
- Lakeland - Winter Haven
- Cypress Gardens
- 1.01 mi to center
383.19 ft²
25 Guests
5 Bathrooms
Ocean View
Resort
- Oceanfront
- Fireplace/Heating
- Pool
CA $360/Night
For 7 Nights CA $2,518
9.8
Exceptional
(737 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 0.25 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
CA $371/Night
For 7 Nights CA $2,598
New
- Lakeland - Winter Haven
- Winter Haven
- 3.20 mi to center
320 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
CA $235/Night
For 7 Nights CA $1,646
6.5
Good
(154 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.93 mi to center
376.74 ft²
10 Guests
3 Bathrooms
Free Cancellation
Resort
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $108/Night
For 7 Nights CA $757
5.0
Average
(3 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.25 mi to center
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Pet Friendly
- Kitchen
- Air Conditioner
CA $200/Night
For 7 Nights CA $1,400
New
- Lakeland - Winter Haven
- Cypress Gardens
- 1.50 mi to center
1722.23 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pool
- Pet Friendly
CA $412/Night
For 7 Nights CA $2,886
New
- Lakeland - Winter Haven
- Winter Haven
- 1.38 mi to center
355 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Hot Tub
- Kitchen
- Air Conditioner
CA $385/Night
For 7 Nights CA $2,694
9.4
Exceptional
(18 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.22 mi to center
2500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
CA $368/Night
For 7 Nights CA $2,572
Winter Haven Private Villas and Holiday Homes Under $200
Over 170+ Winter Haven Private Villas and Holiday Homes Under $200
10.0
Exceptional
(15 Reviews)
- Lakeland - Winter Haven
- Cypress Gardens
- 0.25 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
CA $130/Night
For 7 Nights CA $912
10.0
Exceptional
(2 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 0.93 mi to center
538.2 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Spa
- Fireplace/Heating
- Pet Friendly
CA $163/Night
For 7 Nights CA $1,138
7.2
Very Good
(187 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.94 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $115/Night
For 7 Nights CA $805
10.0
Exceptional
(9 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.82 mi to center
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $207/Night
For 7 Nights CA $1,449
10.0
Exceptional
(1 Review)
1420.84 ft²
8 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- View
- Air Conditioner
CA $252/Night
For 7 Nights CA $1,761
10.0
Exceptional
(7 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 4.07 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $241/Night
For 7 Nights CA $1,686
10.0
Exceptional
(7 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 2.12 mi to center
840 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $233/Night
For 7 Nights CA $1,629
10.0
Exceptional
(2 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 0.92 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Kitchen
- Parking
- Air Conditioner
CA $239/Night
For 7 Nights CA $1,674
10.0
Exceptional
(1 Review)
- Lakeland - Winter Haven
- Winter Haven
- 0.91 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
CA $226/Night
For 7 Nights CA $1,578
Instantly Bookable Holiday Homes in Winter Haven
Over 208+ Instantly Bookable Holiday Homes in or Near Winter Haven
10.0
Exceptional
(3 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 5.76 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $397/Night
For 7 Nights CA $2,779
New
- Lakeland - Winter Haven
- Winter Haven
- 4.42 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
House
CA $372/Night
For 7 Nights CA $2,603
10.0
Exceptional
(3 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.61 mi to center
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $275/Night
For 7 Nights CA $1,923
10.0
Exceptional
(1 Review)
- Lakeland - Winter Haven
- Winter Haven
- 0.56 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
CA $149/Night
For 7 Nights CA $1,045
10.0
Exceptional
(1 Review)
- Lakeland - Winter Haven
- Winter Haven
- 1.49 mi to center
1638 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Parking
CA $137/Night
For 7 Nights CA $959
9.6
Exceptional
(19 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.33 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $178/Night
For 7 Nights CA $1,246
9.6
Exceptional
(7 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 3.43 mi to center
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $243/Night
For 7 Nights CA $1,703
9.4
Exceptional
(12 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.64 mi to center
400 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Private Pool
- Fireplace/Heating
- Pool
CA $140/Night
For 7 Nights CA $978
9.4
Exceptional
(11 Reviews)
- Lakeland - Winter Haven
- Winter Haven
- 1.20 mi to center
400 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $170/Night
For 7 Nights CA $1,190
Book a Last Minute Place to Stay in Winter Haven
About Casai's Private Villas and Holiday Rentals in Winter Haven
Discover more than 411 vacation rentals available in Winter Haven. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winter Haven.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter Haven, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winter Haven. On average, places to stay near Winter Haven offer 930.91 ft², with nightly prices averaging CA $432.
With Casai, finding and comparing holiday rentals in Winter Haven is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Winter Haven
| Type | Count |
|---|---|
| Vacation Homes | 283 |
| Holiday Apartments | 53 |
| Cottages | 10 |
| Villas | 9 |
Use these Quick Filters to Find a Holiday Rental in Winter Haven
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winter Haven.
Weather in Winter Haven, FL
View the weather forecast for Winter Haven before booking your Winter Haven Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Winter Haven, FL
Casai offers a large selection of top attractions around Winter Haven . Research things to do on your vacation before you visit Winter Haven.
Other Places to Stay in Winter Haven, FL
Frequently Asked Questions About Winter Haven?
What are the top holiday rentals in Winter Haven?
With numerous options available in Winter Haven, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winter Haven:
- Private pool lake house with game room—just 4 minutes from LEGOLAND
- Waterfront Winter Haven Home with Dock & Hot Tub!
- Heated Pool and Hot tub-near Legoland, Disney, Theme parks
- Waterfront Lakehouse, Private Dock, Tiki Bar, Playground, Near Legoland | Lake Idylwild Delight
- Lake Rochelle Rental Lakefront
- Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
- 3/2 kid friendly home, only minutes to Legoland.
- Spectacular Waterfront Home in Winter Haven
- Fantastic Water Front Home on the Chain of Lakes
- Cheerful 4 Bed, 3 Bath Home with Screened Pool
How many holiday rentals have private pools in Winter Haven?
Discover a selection of holiday rentals with private pools near Winter Haven with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Lake Shipp House with pool and dock on the water
- Heated Pool, Arcade with PS5, 5min from Legoland-Stylish LakeHome
- Newly remodeled Vacation Home with Saltwater Pool
- Work, Play or Recharge:3BR Pool Home near Legoland
Which holiday homes in Winter Haven are best for families?
If you're searching for a family-friendly holiday home in Winter Haven, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winter Haven:
- 1-bedroom Apartment C near Hospitals/Legoland/Chain of Lakes
- Peaceful waterfront home minutes from Legoland, Fl
- BlockHaven near Legoland & Disney
How many Casai.ca holiday rentals are available in Winter Haven?
As of 2026, Casai boasts over 411 properties listed in the Winter Haven area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter Haven.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Winterset Gardens Vacation Rentals in Winter Haven, Florida | 149 |
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