House
10.0(69 Reviews)
1 Bedroom
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
R3,563/Night
7 Nights - R24,947
Winter Garden Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Winter Garden
10.0
House
10.0(7 Reviews)
1 Bedroom
4 Guests
- Parking
Spa- Balcony/Terrace
Internet
R2,728/Night
7 Nights - R19,092
R16,564/Night
7 Nights - R115,946
House
10.0(36 Reviews)
2 Bedrooms
6 Guests
Hot Tub- Parking
Pool- Spa
R2,897/Night
7 Nights - R20,273
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Spa
- Internet
Pet Friendly
R5,112/Night
7 Nights - R35,789
House
10.0(35 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R4,554/Night
7 Nights - R31,869
House
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
Ocean View
R2,744/Night
7 Nights - R19,207
House
10.0(9 Reviews)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
R5,531/Night
7 Nights - R38,709
Apartment
10.0(8 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R6,614/Night
7 Nights - R46,303
Luxury Holiday Rentals in Winter Garden
Over 399+ Luxury Holiday Rentals in or Near Winter Garden
Resort
12 Guests
- Pool
- Air Conditioner
- Internet
- Child Friendly
R16,046/Night
7 Nights - R112,321
House
10.0(1 Review)
5 Bedrooms
13 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
R14,056/Night
7 Nights - R98,396
House
3 Bedrooms
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
R11,824/Night
7 Nights - R82,765
New
House
7 Bedrooms
16 Guests
Private Pool- Parking
- Pool
- Balcony/Terrace
R9,054/Night
7 Nights - R63,377
Apartment
1 Bedroom
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R8,882/Night
7 Nights - R62,180
R8,668/Night
7 Nights - R60,671
House
9.6(12 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R8,447/Night
7 Nights - R59,129
House
10.0(34 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
R8,388/Night
7 Nights - R58,719
Cottage
1 Bedroom
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
R8,187/Night
7 Nights - R57,309
Top-Rated Holiday Rentals with a Pool in Winter Garden
Over 233+ The Best Private Villas and Holiday Rentals in Winter Garden with a Pool
Resort
10.0(7 Reviews)
8 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
R3,267/Night
7 Nights - R22,864
Apartment
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R4,638/Night
7 Nights - R32,476
Resort
10.0(2 Reviews)
8 Guests
Breakfast- Parking
- Pool
- Balcony/Terrace
R4,521/Night
7 Nights - R31,656
Villa
10.0(2 Reviews)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R3,425/Night
7 Nights - R23,980
Villa
10.0(2 Reviews)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R3,425/Night
7 Nights - R23,980
Apartment
10.0(2 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R3,354/Night
7 Nights - R23,488
Condo
10.0(1 Review)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R6,122/Night
7 Nights - R42,858
Condo
10.0(1 Review)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R5,533/Night
7 Nights - R38,725
Apartment
10.0(1 Review)
2 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R4,913/Night
7 Nights - R34,395
Pet-Friendly Holiday Rentals in Winter Garden
Over 49+ Pet-Friendly Holiday Rentals in or Near Winter Garden
House
10.0(7 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R4,576/Night
7 Nights - R32,033
Apartment
8.4(12 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
View- Air Conditioner
R2,418/Night
7 Nights - R16,927
Apartment
9.6(15 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,428/Night
7 Nights - R23,996
Apartment
10.0(2 Reviews)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
R3,049/Night
7 Nights - R21,339
House
8.3(38 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
R1,214/Night
7 Nights - R8,496
House
9.8(28 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R4,994/Night
7 Nights - R34,969
Apartment
9.8(23 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,313/Night
7 Nights - R23,192
Cottage
9.6(52 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,676/Night
7 Nights - R39,726
Villa
9.6(5 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,531/Night
7 Nights - R24,718
Large Holiday Rentals and Private Villas in Winter Garden
Over 62+ Large Holiday Rentals and Private Villas in or Near Winter Garden
Villa
10.0(1 Review)
1 Bedroom
4 Guests
Oceanfront- Hot Tub
- Parking
- Pool
R4,158/Night
7 Nights - R29,114
Villa
2 Bedrooms
9 Guests
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
R2,674/Night
7 Nights - R18,715
Villa
9.6(8 Reviews)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R3,425/Night
7 Nights - R23,980
Villa
9.2(109 Reviews)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R4,162/Night
7 Nights - R29,130
Villa
9.2(5 Reviews)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R4,122/Night
7 Nights - R28,851
Villa
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R6,452/Night
7 Nights - R45,171
Villa
2 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R6,379/Night
7 Nights - R44,646
Villa
2 Bedrooms
8 Guests
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
R6,159/Night
7 Nights - R43,121
Villa
2 Bedrooms
8 Guests
Security/Safety
R5,989/Night
7 Nights - R41,924
Wheelchair Accessible Holiday Homes in Winter Garden
Over 88+ Wheelchair Accessible Holiday Homes in or Near Winter Garden
Condo
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
R5,533/Night
7 Nights - R38,725
Resort
8.4(2307 Reviews)
100 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
R2,293/Night
7 Nights - R16,058
R2,179/Night
7 Nights - R15,254
R5,135/Night
7 Nights - R35,937
R2,163/Night
7 Nights - R15,139
Villa
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R4,205/Night
7 Nights - R29,442
New
Villa
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
R4,054/Night
7 Nights - R28,375
Villa
2 Bedrooms
8 Guests
- Breakfast
- Parking
- Pool
- Balcony/Terrace
R2,942/Night
7 Nights - R20,585
Resort
9.8(11 Reviews)
8 Guests
- Breakfast
- Parking
- Pool
- Balcony/Terrace
R2,874/Night
7 Nights - R20,109
Winter Garden Private Villas and Holiday Homes Under $200
Over 143+ Winter Garden Private Villas and Holiday Homes Under $200
Apartment
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,653/Night
7 Nights - R18,567
House
8.0(5 Reviews)
1 Bedroom
5 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
R2,418/Night
7 Nights - R16,927
Bed & Breakfast
9.6(309 Reviews)
1 Bedroom
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
R2,426/Night
7 Nights - R16,976
Condo
10.0(1 Review)
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
R2,911/Night
7 Nights - R20,388
House
5.0(1 Review)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Internet
- Laundry
R2,214/Night
7 Nights - R15,500
Apartment
9.4(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,259/Night
7 Nights - R15,812
House
9.0(24 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R1,810/Night
7 Nights - R12,662
Apartment
8.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R2,386/Night
7 Nights - R16,697
Apartment
2.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R2,873/Night
7 Nights - R20,109
Instantly Bookable Holiday Homes in Winter Garden
Over 202+ Instantly Bookable Holiday Homes in or Near Winter Garden
House
9.8(49 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R4,409/Night
7 Nights - R30,869
Apartment
9.8(24 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R5,375/Night
7 Nights - R37,626
Cottage
9.6(18 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,468/Night
7 Nights - R24,275
Apartment
9.2(10 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R4,720/Night
7 Nights - R33,034
House
9.2(10 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R3,641/Night
7 Nights - R25,489
House
9.0(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
R4,385/Night
7 Nights - R30,688
Apartment
8.8(3 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R4,286/Night
7 Nights - R29,999
R3,988/Night
7 Nights - R27,916
Apartment
1 Bedroom
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R5,952/Night
7 Nights - R41,661
Book a Last Minute Place to Stay in Winter Garden
About Casai's Private Villas and Holiday Rentals in Winter Garden
Discover more than 408 vacation rentals available in Winter Garden. 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 Garden.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter Garden, 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 Garden. On average, places to stay near Winter Garden offer 677.09 ft², with nightly prices averaging R4,053.
With Casai, finding and comparing holiday rentals in Winter Garden 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 in Winter Garden, FL
There are 408 Winter Garden, FL Holiday Rentals
- Prices for a holiday home in Winter Garden start at R1,214
- Top rated vacation home in Winter Garden is Walkable Winter Garden Bungalow: 3 Blocks to Dtwn
- Most popular short term in Winter Garden is Holiday Inn Club Vacations At Orange Lake Resort
- Cheapest place to stay in Winter Garden is Near Disney cozy quiet place, up to 2 rooms with queen bed up to 4 people
- Most expensive holiday rental in Winter Garden is Oakland Manor House
Recently Booked Holiday Rentals in Winter Garden
Frequently Asked Questions About Winter Garden?
What are the top holiday rentals in Winter Garden?
With numerous options available in Winter Garden, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winter Garden:
- Walkable Winter Garden Bungalow: 3 Blocks to Dtwn
- 25%off/Disney5mi/Fishing/2HotTub/3Pools/Gym/Courts
- Spacious garage apartment in Winter Garden that sleeps four.
- WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn
- 2-bedroom home 5 miles to Disney on Lake. Four Corners. Vista Del Lago amenities
- Downtown Winter Garden bungalow with private putting green and fire pit
- Cozy 2 Bedroom Apartment in Winter Garden with fast wifi, pool & fitness room
- 1921 2BD/1BTH Bungalow - Historic Winter Garden, Steps to Plant St, Dogs Welcome
- Cozy 1-2-bedroom resort less than 20 minutes away from Orlando theme parks.
- Walkable Winter Garden Bungalow: 3 Blocks to Dtwn
How many holiday rentals have private pools in Winter Garden?
Discover a selection of holiday rentals with private pools near Winter Garden 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 Garden are best for families?
If you're searching for a family-friendly holiday home in Winter Garden, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winter Garden:
How many Casai.co.za holiday rentals are available in Winter Garden?
As of 2026, Casai boasts over 408 properties listed in the Winter Garden area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter Garden.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| West Kissimmee Vacation Rentals in Orlando, Florida | 15316 |
| Bay Lake Vacation Rentals in Orlando, Florida | 804 |
| Orange Lake Vacation Rentals in Orlando, Florida | 80 |
| Vista del Lago Vacation Rentals in Orlando, Florida | 15204 |
| Oakland Vacation Rentals in Orlando, Florida | 92 |
| Killarney Vacation Rentals in Orlando, Florida | 37 |
