Apartment
10.0(33 Reviews)
1 Bedroom
4 Guests
Hot Tub
Parking
Balcony/Terrace
Kitchen
US $289/Night
7 Nights - US $2,024
Winter Haven Holiday Rentals
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Compare Villas, Resorts, & Rentals in Winter Haven
10.0
House
10.0(9 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
View
Internet
US $255/Night
7 Nights - US $1,785
House
10.0(8 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
US $263/Night
7 Nights - US $1,842
Apartment
10.0(32 Reviews)
2 Bedrooms
6 Guests
- Parking
Pool
Ocean View- Balcony/Terrace
US $259/Night
7 Nights - US $1,815
House
10.0(4 Reviews)
4 Bedrooms
17 Guests
Breakfast- Parking
- Pool
- Balcony/Terrace
US $1,170/Night
7 Nights - US $8,188
Apartment
10.0(22 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $246/Night
7 Nights - US $1,723
House
10.0(20 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $107/Night
7 Nights - US $748
Apartment
10.0(18 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $129/Night
7 Nights - US $902
Apartment
10.0(9 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $151/Night
7 Nights - US $1,056
Luxury Holiday Rentals in Winter Haven
Over 420+ Luxury Holiday Rentals in or Near Winter Haven
House
2 Bedrooms
12 Guests
- Air Conditioner
- Internet
Security/Safety
US $1,875/Night
7 Nights - US $13,125
House
3 Bedrooms
10 Guests
- Parking
- Air Conditioner
- Internet
- Security/Safety
US $1,875/Night
7 Nights - US $13,125
House
10.0(6 Reviews)
4 Bedrooms
16 Guests
Private Pool- Hot Tub
- Parking
- Pool
US $1,231/Night
7 Nights - US $8,618
House
10.0(1 Review)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,006/Night
7 Nights - US $7,044
US $804/Night
7 Nights - US $5,630
House
10.0(28 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $804/Night
7 Nights - US $5,627
House
10.0(12 Reviews)
5 Bedrooms
16 Guests
Oceanfront- Parking
- Pool
- Ocean View
US $730/Night
7 Nights - US $5,112
Hotel
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $714/Night
7 Nights - US $4,996
Top-Rated Holiday Rentals with a Pool in Winter Haven
Over 144+ The Best Private Villas and Holiday Rentals in Winter Haven with a Pool
House
10.0(83 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $460/Night
7 Nights - US $3,218
House
10.0(72 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $549/Night
7 Nights - US $3,842
House
10.0(71 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $341/Night
7 Nights - US $2,390
House
10.0(36 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $458/Night
7 Nights - US $3,203
House
10.0(29 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $525/Night
7 Nights - US $3,672
House
10.0(20 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $663/Night
7 Nights - US $4,642
House
10.0(17 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $487/Night
7 Nights - US $3,406
House
10.0(13 Reviews)
4 Bedrooms
11 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $548/Night
7 Nights - US $3,834
House
10.0(13 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $316/Night
7 Nights - US $2,215
Pet-Friendly Holiday Rentals in Winter Haven
Over 120+ Pet-Friendly Holiday Rentals in or Near Winter Haven
House
10.0(4 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,316
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
Spa- Internet
Pet Friendly
US $107/Night
7 Nights - US $749
US $506/Night
7 Nights - US $3,542
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $353/Night
7 Nights - US $2,474
House
10.0(2 Reviews)
4 Bedrooms
22 Guests
- Hot Tub
- Parking
- Internet
- Pet Friendly
US $491/Night
7 Nights - US $3,437
Cottage
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $248/Night
7 Nights - US $1,739
New
Ski Chalet
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $237/Night
7 Nights - US $1,659
House
9.8(11 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $239/Night
7 Nights - US $1,672
Apartment
8.4(9 Reviews)
1 Bedroom
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $183/Night
7 Nights - US $1,284
Large Holiday Rentals and Private Villas in Winter Haven
Over 74+ Large Holiday Rentals and Private Villas in or Near Winter Haven
Villa
2 Bedrooms
3 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $250/Night
7 Nights - US $1,749
House
10.0(3 Reviews)
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $200/Night
7 Nights - US $1,400
House
10.0(26 Reviews)
4 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $435/Night
7 Nights - US $3,047
House
10.0(1 Review)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $315/Night
7 Nights - US $2,205
House
10.0(13 Reviews)
3 Bedrooms
10 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $279/Night
7 Nights - US $1,953
House
10.0(8 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $425/Night
7 Nights - US $2,977
House
10.0(8 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $371/Night
7 Nights - US $2,596
House
10.0(2 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $512/Night
7 Nights - US $3,581
House
10.0(2 Reviews)
5 Bedrooms
12 Guests
- Air Conditioner
- Internet
- Pet Friendly
Laundry
US $361/Night
7 Nights - US $2,529
Wheelchair Accessible Holiday Homes in Winter Haven
Over 24+ Wheelchair Accessible Holiday Homes in or Near Winter Haven
House
9.4(13 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $397/Night
7 Nights - US $2,779
Resort
8.1(1427 Reviews)
25 Guests
- Oceanfront
EV Charge Station- Parking
- Pool
US $263/Night
7 Nights - US $1,838
Hotel
9.8(916 Reviews)
- Breakfast
- Pool
- Kitchen
- Air Conditioner
US $155/Night
7 Nights - US $1,082
House
5.0(3 Reviews)
3 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Pet Friendly
Child Friendly
US $146/Night
7 Nights - US $1,022
US $79/Night
7 Nights - US $553
House
1 Bedroom
3 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
US $281/Night
7 Nights - US $1,967
House
3 Bedrooms
8 Guests
- Pool
- Air Conditioner
- Pet Friendly
Wheelchair Accessible
US $347/Night
7 Nights - US $2,427
House
1 Bedroom
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $172/Night
7 Nights - US $1,202
House
9.4(18 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $268/Night
7 Nights - US $1,878
Winter Haven Private Villas and Holiday Homes Under $200
Over 165+ Winter Haven Private Villas and Holiday Homes Under $200
Condo
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $159/Night
7 Nights - US $1,112
House
10.0(2 Reviews)
3 Bedrooms
7 Guests
- EV Charge Station
- Parking
- Spa
- Air Conditioner
US $156/Night
7 Nights - US $1,089
US $155/Night
7 Nights - US $1,086
Apartment
10.0(2 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $160/Night
7 Nights - US $1,122
House
10.0(2 Reviews)
2 Bedrooms
8 Guests
- View
- Air Conditioner
- Internet
- Security/Safety
US $172/Night
7 Nights - US $1,202
House
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $109/Night
7 Nights - US $765
New
Cottage
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Ocean View
- View
- Kitchen
US $172/Night
7 Nights - US $1,202
Apartment
10.0(1 Review)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $136/Night
7 Nights - US $952
Apartment
9.8(32 Reviews)
1 Bedroom
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $103/Night
7 Nights - US $720
Instantly Bookable Holiday Homes in Winter Haven
Over 223+ Instantly Bookable Holiday Homes in or Near Winter Haven
Cottage
10.0(7 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $237/Night
7 Nights - US $1,656
US $271/Night
7 Nights - US $1,900
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $212/Night
7 Nights - US $1,485
Cottage
9.8(21 Reviews)
1 Bedroom
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $140/Night
7 Nights - US $977
Apartment
9.8(20 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $118/Night
7 Nights - US $826
Apartment
9.6(14 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $130/Night
7 Nights - US $908
House
9.6(8 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $235/Night
7 Nights - US $1,643
Apartment
9.6(7 Reviews)
2 Bedrooms
7 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $385/Night
7 Nights - US $2,693
House
9.4(21 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $163/Night
7 Nights - US $1,140
Book a Last Minute Place to Stay in Winter Haven
About Casai's Private Villas and Holiday Rentals in Winter Haven
Discover more than 429 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 942.2 ft², with nightly prices averaging US $298.
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.
Other places to stay near the Winter Haven, FL
There are 429 Winter Haven, FL Holiday Rentals
- Prices for a holiday home in Winter Haven start at US $64
- Top rated vacation home in Winter Haven is Private pool lake house with game room—just 4 minutes from LEGOLAND
- Most popular short term in Winter Haven is LEGOLAND® Florida Resort
- Cheapest place to stay in Winter Haven is Economy Suites
- Most expensive holiday rental in Winter Haven is 146 Florida 3BR Home close to Legoland Park 12ppl
Recently Booked Holiday Rentals in Winter Haven
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!
- Legoland Splash Escape with pool and hot tub!
- Lakefront Family Retreat | Private Dock, Tiki Bar & Kayaks | Near Legoland
- Lake Rochelle Rental Lakefront
- Beautiful Lake Front cottage w/heated pool & Hot Tub, 23 miles from Disney
- Hot Tub & Fire Pit: Lakefront Home on Lake Eloise
- 2-bedroom, 2-bath unit offers a family-friendly retreat just mins from LEGOLAND.
- 3/2 kid friendly home, only minutes to Legoland.
- Fantastic Water Front Home on the Chain of Lakes
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.
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:
How many Casai.com holiday rentals are available in Winter Haven?
As of 2026, Casai boasts over 429 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 |
