Apartment
10.0(33 Reviews)
2 Bedrooms
6 Guests
Parking
Pool
Balcony/Terrace
Kitchen
US $245/Night
7 Nights - US $1,716
Winter Haven, FL 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 $258/Night
7 Nights - US $1,807
Apartment
10.0(22 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $245/Night
7 Nights - US $1,716
House
10.0(4 Reviews)
4 Bedrooms
17 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $1,170/Night
7 Nights - US $8,188
Apartment
10.0(21 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $120/Night
7 Nights - US $840
Apartment
10.0(18 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $130/Night
7 Nights - US $909
Apartment
10.0(9 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $144/Night
7 Nights - US $1,011
Condo
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $168/Night
7 Nights - US $1,173
Luxury Holiday Rentals in Winter Haven
Over 424+ 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(8 Reviews)
4 Bedrooms
16 Guests
Private Pool
Hot Tub- Parking
- Pool
US $867/Night
7 Nights - US $6,066
US $804/Night
7 Nights - US $5,630
House
10.0(1 Review)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $777/Night
7 Nights - US $5,438
House
10.0(12 Reviews)
5 Bedrooms
16 Guests
- Parking
- Pool
Ocean View- Balcony/Terrace
US $759/Night
7 Nights - US $5,311
House
10.0(28 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $756/Night
7 Nights - US $5,292
House
4 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $695/Night
7 Nights - US $4,865
Top-Rated Holiday Rentals with a Pool in Winter Haven
Over 140+ The Best Private Villas and Holiday Rentals in Winter Haven with a Pool
House
10.0(84 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $411/Night
7 Nights - US $2,874
House
10.0(74 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $335/Night
7 Nights - US $2,348
House
10.0(72 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $547/Night
7 Nights - US $3,826
House
10.0(36 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $450/Night
7 Nights - US $3,152
House
10.0(29 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $524/Night
7 Nights - US $3,665
House
10.0(20 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $656/Night
7 Nights - US $4,593
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(15 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $340/Night
7 Nights - US $2,381
House
10.0(14 Reviews)
3 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $297/Night
7 Nights - US $2,082
Pet-Friendly Holiday Rentals in Winter Haven
Over 119+ Pet-Friendly Holiday Rentals in or Near Winter Haven
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $340/Night
7 Nights - US $2,383
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
Spa- Internet
Pet Friendly
US $107/Night
7 Nights - US $749
House
1 Bedroom
- Parking
- Pool
- Internet
- Pet Friendly
US $456/Night
7 Nights - US $3,193
Ski Chalet
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $223/Night
7 Nights - US $1,564
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 $206/Night
7 Nights - US $1,443
House
9.8(11 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $257/Night
7 Nights - US $1,798
Condo
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $189/Night
7 Nights - US $1,325
Apartment
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,014
Large Holiday Rentals and Private Villas in Winter Haven
Over 77+ Large Holiday Rentals and Private Villas in or Near Winter Haven
House
10.0(26 Reviews)
4 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $416/Night
7 Nights - US $2,912
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)
4 Bedrooms
11 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $563/Night
7 Nights - US $3,940
House
10.0(1 Review)
1 Bedroom
12 Guests
EV Charge Station- Parking
- Pool
- Balcony/Terrace
US $383/Night
7 Nights - US $2,678
House
10.0(8 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $509/Night
7 Nights - US $3,562
House
10.0(3 Reviews)
5 Bedrooms
12 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $339/Night
7 Nights - US $2,371
House
9.8(33 Reviews)
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $475/Night
7 Nights - US $3,328
House
9.8(30 Reviews)
4 Bedrooms
11 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $396/Night
7 Nights - US $2,773
House
9.6(31 Reviews)
4 Bedrooms
22 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $421/Night
7 Nights - US $2,947
Wheelchair Accessible Holiday Homes in Winter Haven
Over 22+ Wheelchair Accessible Holiday Homes in or Near Winter Haven
New
House
9.4(13 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $413/Night
7 Nights - US $2,888
Resort
8.1(1427 Reviews)
25 Guests
- EV Charge Station
- Parking
- Pool
- Balcony/Terrace
US $263/Night
7 Nights - US $1,838
Hotel
9.8(920 Reviews)
Breakfast- Pool
- Kitchen
- Air Conditioner
US $179/Night
7 Nights - US $1,254
House
9.4(18 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $268/Night
7 Nights - US $1,878
US $79/Night
7 Nights - US $553
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 $117/Night
7 Nights - US $819
House
1 Bedroom
3 Guests
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
US $281/Night
7 Nights - US $1,967
House
1 Bedroom
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $172/Night
7 Nights - US $1,202
Winter Haven Private Villas and Holiday Homes Under $200
Over 164+ Winter Haven Private Villas and Holiday Homes Under $200
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)
3 Bedrooms
7 Guests
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $156/Night
7 Nights - US $1,089
US $146/Night
7 Nights - US $1,022
House
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $112/Night
7 Nights - US $782
House
10.0(2 Reviews)
2 Bedrooms
8 Guests
- View
- Air Conditioner
- Internet
- Security/Safety
US $169/Night
7 Nights - US $1,181
Apartment
10.0(1 Review)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $140/Night
7 Nights - US $980
Apartment
9.8(34 Reviews)
1 Bedroom
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $96/Night
7 Nights - US $674
House
9.4(21 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $162/Night
7 Nights - US $1,135
Apartment
9.4(16 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $130/Night
7 Nights - US $908
Instantly Bookable Holiday Homes in Winter Haven
Over 226+ 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 $239/Night
7 Nights - US $1,670
House
10.0(26 Reviews)
4 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $417/Night
7 Nights - US $2,920
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $209/Night
7 Nights - US $1,466
New
Cottage
10.0(2 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $210/Night
7 Nights - US $1,473
House
9.6(8 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $233/Night
7 Nights - US $1,631
Apartment
9.6(7 Reviews)
2 Bedrooms
7 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $386/Night
7 Nights - US $2,700
Apartment
9.4(13 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $119/Night
7 Nights - US $836
Cottage
9.2(7 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $279/Night
7 Nights - US $1,951
Cottage
9.0(42 Reviews)
2 Bedrooms
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $149/Night
7 Nights - US $1,042
Book a Last Minute Place to Stay in Winter Haven
About Casai's Private Villas and Holiday Rentals in Winter Haven
Discover more than 433 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 923.52 ft², with nightly prices averaging US $297.
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 433 Winter Haven, FL Holiday Rentals
- Prices for a holiday home in Winter Haven start at US $55
- 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 Traveling workers w/full kitchen and living space
- 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
- Legoland Splash Escape with pool and hot tub!
- Waterfront Winter Haven Home with Dock & 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 433 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 |
