Holiday rentals near Winter Park Country Club
We found 5,769 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 AU$2,155
AU$2,155
AU$308 nightly
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 AU$6,219
AU$6,219
AU$888 nightly
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 AU$2,850
AU$2,850
AU$407 nightly
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 AU$3,185
AU$3,185
AU$455 nightly
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 AU$4,758
AU$4,758
AU$680 nightly
Includes taxes & fees
Image gallery for Cozy Suite in the Heart of Orlando near Universal Hot Tub Spa
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Cozy Suite in the Heart of Orlando near Universal Hot Tub Spa
Orlando, FL
16% off
Price is AU$986
AU$986
AU$141 nightly
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 AU$2,439
AU$2,439
AU$348 nightly
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
7% off
Price is AU$2,477
AU$2,477
AU$354 nightly
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 AU$3,669
AU$3,669
AU$524 nightly
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 AU$1,818
AU$1,818
AU$260 nightly
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 AU$6,577
AU$6,577
AU$940 nightly
Includes taxes & fees
Image gallery for A Delightful Retreat 3/2 1/2 bath Countryside
9.89.8 out of 10 rating
Exceptional
(21 reviews)
A Delightful Retreat 3/2 1/2 bath Countryside
Sanford, FL
7% off
Price is AU$3,508
AU$3,508
AU$501 nightly
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 AU$1,716
AU$1,716
AU$245 nightly
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 AU$4,655
AU$4,655
AU$665 nightly
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 AU$1,575
AU$1,575
AU$225 nightly
Includes taxes & fees
Image gallery for Floating Cottage Summer and Fall Rates Reduced
1010 out of 10 rating
Exceptional
(157 reviews)
Floating Cottage Summer and Fall Rates Reduced
Sanford, FL
11% off
Price is AU$1,943
AU$1,943
AU$278 nightly
Includes taxes & fees
Image gallery for Home away from Home Luxury 2 bed/2bath Country Club Condo
9.69.6 out of 10 rating
Exceptional
(58 reviews)
Home away from Home Luxury 2 bed/2bath Country Club Condo
Orlando, FL
8% off
Price is AU$1,575
AU$1,575
AU$225 nightly
Includes taxes & fees
Image gallery for CountryClub 2/2 Home Away from Home
9.49.4 out of 10 rating
Exceptional
(63 reviews)
CountryClub 2/2 Home Away from Home
Orlando, FL
8% off
Price is AU$1,575
AU$1,575
AU$225 nightly
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 AU$2,221
AU$2,221
AU$317 nightly
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 AU$3,918
AU$3,918
AU$560 nightly
Includes taxes & fees
Image gallery for THE OLIVIA by EVRH
8.88.8 out of 10 rating
Excellent
(34 reviews)
THE OLIVIA by EVRH
Altamonte Springs, FL
7% off
Price is AU$2,664
AU$2,664
AU$381 nightly
Includes taxes & fees
Image gallery for Upscale Stay: Minutes from Parks, Convention Center and attractions.
1010 out of 10 rating
Exceptional
(41 reviews)
Upscale Stay: Minutes from Parks, Convention Center and attractions.
Orlando, FL
12% off
Price is AU$3,001
AU$3,001
AU$429 nightly
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 AU$3,936
AU$3,936
AU$562 nightly
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 AU$8,730
AU$8,730
AU$1,247 nightly
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
2,775 reviews(2,775 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
26 reviews(26 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
433 reviews(433 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