Holiday rentals near Winter Park Country Club
We found 5,877 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Winter Park Country Club, take a look at holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the amenities that you expect and more, such as air conditioning and a TV. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Winter Park Country Club
Showing deals for:21 Nov - 28 Nov
Image gallery for Downtown Floating Bungalow Historic Sanford Lake Monroe Marina
1010 out of 10 rating
Exceptional
(57 reviews)
Downtown Floating Bungalow Historic Sanford Lake Monroe Marina
Sanford, FL
8% off
Price is S$1,756
S$1,756
S$251 per night
includes taxes & fees
Image gallery for Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
1010 out of 10 rating
Exceptional
(49 reviews)
Magnificent Lakefront House • Swim/Boat/Relax • EV Charger • Long term stays OK
Apopka, FL
16% off
Price is S$5,151
S$5,151
S$736 per night
includes taxes & fees
Image gallery for Temporary living that feels like home where you can relax and be yourself.
1010 out of 10 rating
Exceptional
(144 reviews)
Temporary living that feels like home where you can relax and be yourself.
Maitland, FL
8% off
Price is S$1,939
S$1,939
S$277 per night
includes taxes & fees
Image gallery for 4 Bedroom 2 Bath Pet-Friendly Pool Home Orlando Airport
9.89.8 out of 10 rating
Exceptional
(10 reviews)
4 Bedroom 2 Bath Pet-Friendly Pool Home Orlando Airport
Orlando, FL
11% off
Price is S$2,640
S$2,640
S$377 per night
includes taxes & fees
Image gallery for Lake Lucy Waterfront Home with BBQ & Jon Boat
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Lake Lucy Waterfront Home with BBQ & Jon Boat
Orlando, FL
12% off
Price is S$2,363
S$2,363
S$338 per night
includes taxes & fees
Image gallery for Pool+Grill+Huge yard+outdoor movies+Plenty parking space
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Pool+Grill+Huge yard+outdoor movies+Plenty parking space
Apopka, FL
5% off
Price is S$3,860
S$3,860
S$551 per night
includes taxes & fees
Image gallery for Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
9.09.0 out of 10 rating
Wonderful
(22 reviews)
Winter Park Citrus Escape; sleeps 8, relaxing pool, family & pet friendly
Winter Park, FL
8% off
Price is S$3,854
S$3,854
S$551 per night
includes taxes & fees
Image gallery for Walk into Tropical Paradise - POOL - GYM - HOT TUB
1010 out of 10 rating
Exceptional
(5 reviews)
Walk into Tropical Paradise - POOL - GYM - HOT TUB
Altamonte Springs, FL
8% off
Price is S$5,433
S$5,433
S$776 per night
includes taxes & fees
Image gallery for Fully renovated home in Lake Mary
1010 out of 10 rating
Exceptional
(5 reviews)
Fully renovated home in Lake Mary
Lake Mary, FL
12% off
Price is S$3,296
S$3,296
S$471 per night
includes taxes & fees
Image gallery for Lakeside and Beautiful
1010 out of 10 rating
Exceptional
(29 reviews)
Lakeside and Beautiful
Sanford, FL
7% off
Price is S$1,988
S$1,988
S$284 per night
includes taxes & fees
Image gallery for Beautiful 3 Bedroom 2 full bath 2 car 🚗 garage.
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful 3 Bedroom 2 full bath 2 car 🚗 garage.
Oviedo, FL
13% off
Price is S$3,042
S$3,042
S$435 per night
includes taxes & fees
Image gallery for * Beautiful Lakehouse with Pool and Movie Theater*
9.69.6 out of 10 rating
Exceptional
(31 reviews)
* Beautiful Lakehouse with Pool and Movie Theater*
Casselberry, FL
8% off
Price is S$7,680
S$7,680
S$1,097 per night
includes taxes & fees
Image gallery for Salt Pool, cozy House near Downtown and International Airport
9.69.6 out of 10 rating
Exceptional
(80 reviews)
Salt Pool, cozy House near Downtown and International Airport
Orlando, FL
8% off
Price is S$2,018
S$2,018
S$288 per night
includes taxes & fees
Image gallery for Near Disney and USTA tennis campus - Pool Villa on the Lake - Stunning Views!
9.89.8 out of 10 rating
Exceptional
(62 reviews)
Near Disney and USTA tennis campus - Pool Villa on the Lake - Stunning Views!
Kissimmee, FL
8% off
Price is S$3,248
S$3,248
S$464 per night
includes taxes & fees
Image gallery for Spacious Vacation Home 20 min from Theme Parks!
9.29.2 out of 10 rating
Wonderful
(56 reviews)
Spacious Vacation Home 20 min from Theme Parks!
Kissimmee, FL
7% off
Price is S$2,139
S$2,139
S$306 per night
includes taxes & fees
Image gallery for Orlando Happy Guest House by Universal Studios
1010 out of 10 rating
Exceptional
(12 reviews)
Orlando Happy Guest House by Universal Studios
Orlando, FL
8% off
Price is S$1,810
S$1,810
S$259 per night
includes taxes & fees
Image gallery for Recharge @ Timberland Lodge: Pool Hottub Sauna
1010 out of 10 rating
Exceptional
(11 reviews)
Recharge @ Timberland Lodge: Pool Hottub Sauna
Longwood, FL
8% off
Price is S$6,470
S$6,470
S$924 per night
includes taxes & fees
Image gallery for Orlando 20 Guest Villa Centrally Located with Game Room
1010 out of 10 rating
Exceptional
(6 reviews)
Orlando 20 Guest Villa Centrally Located with Game Room
Windermere, FL
16% off
Price is S$3,234
S$3,234
S$462 per night
includes taxes & fees
Image gallery for Retreat | Lake Hot Tub Paddle Boards Speakeasy
1010 out of 10 rating
Exceptional
(15 reviews)
Retreat | Lake Hot Tub Paddle Boards Speakeasy
Orlando, FL
8% off
Price is S$6,032
S$6,032
S$862 per night
includes taxes & fees
Image gallery for * Luxury Pool * Hot Tub * 86 Inch TV *
9.89.8 out of 10 rating
Exceptional
(21 reviews)
* Luxury Pool * Hot Tub * 86 Inch TV *
Apopka, FL
13% off
Price is S$4,792
S$4,792
S$685 per night
includes taxes & fees
Image gallery for Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Luxury Floating House - Boat Tree Marina on St. John’s River, Sanford
Sanford, FL
8% off
Price is S$1,494
S$1,494
S$213 per night
includes taxes & fees
Image gallery for Tropical Oasis - Heated Luxury Pool - Game Room
1010 out of 10 rating
Exceptional
(19 reviews)
Tropical Oasis - Heated Luxury Pool - Game Room
Longwood, FL
8% off
Price is S$5,353
S$5,353
S$765 per night
includes taxes & fees
Image gallery for Luxury Golf Country Club Condo 2 Bedroom 2 Bathroom
9.69.6 out of 10 rating
Exceptional
(54 reviews)
Luxury Golf Country Club Condo 2 Bedroom 2 Bathroom
Orlando, FL
8% off
Price is S$1,293
S$1,293
S$185 per night
includes taxes & fees
Image gallery for Lakefront Artist's Loft - Isolate in Luxury!
9.69.6 out of 10 rating
Exceptional
(55 reviews)
Lakefront Artist's Loft - Isolate in Luxury!
Orlando, FL
8% off
Price is S$1,409
S$1,409
S$201 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winter Park Country Club
The Ultimate 10,350 sq ft Orlando Estate - Your Private Resort Near Disney
Sleeps 28 · 8 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Vacation Village at Parkway
Sleeps 8 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
2,761 reviews(2,761 reviews)
Spacious Bowling Villa, Lake Views, 14 Bdr/14bath, close to Disney, Sleeps 38
Sleeps 38 · 14 bedrooms · 14+ bathrooms
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Lakeview Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
382 reviews(382 reviews)
Modern Luxury Villa with Everything
Sleeps 19 · 8 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
432 reviews(432 reviews)
Close to Attractions! Comfy Unit, Pool, Shuttle to Parks, Parking, Breakfast
Sleeps 4 · 1 bedroom · 1 bathroom
6.86.8 out of 10
196 reviews(196 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value