
Holiday rentals near Windermere Country Club
We found 34,114 holiday rentals — enter your dates for availability
If you'd like to stay close to Windermere Country Club, scroll through and discover holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the amenities that you need and want, which might include a hot tub and garden. At the end of the day, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Windermere Country Club
Showing deals for:14 Nov - 21 Nov
Image gallery for Peaceful home with Pool Dog friendly 4 Bedrooms 3 Bathrooms backyard view water.

9.89.8 out of 10 rating
Exceptional
(37 reviews)
Peaceful home with Pool Dog friendly 4 Bedrooms 3 Bathrooms backyard view water.
Davenport, FL
10% off
Price is NZ$2,262
NZ$2,262
NZ$323 per night
includes taxes & fees
Image gallery for 10 min to Disney, private pool home on luxury resort, brand new hardwood floors.

9.49.4 out of 10 rating
Exceptional
(48 reviews)
10 min to Disney, private pool home on luxury resort, brand new hardwood floors.
Kissimmee, FL
11% off
Price is NZ$7,884
NZ$7,884
NZ$1,126 per night
includes taxes & fees
Image gallery for ⭐⭐⭐⭐⭐ NEW LOWER RATES! 8BR/5BA Resort Community/Private Pool/Spa/Theater

9.89.8 out of 10 rating
Exceptional
(48 reviews)
⭐⭐⭐⭐⭐ NEW LOWER RATES! 8BR/5BA Resort Community/Private Pool/Spa/Theater
Davenport, FL
7% off
Price is NZ$4,707
NZ$4,707
NZ$672 per night
includes taxes & fees
Image gallery for No Cleaning Fee! Luxury Villa Awaits! Close to Disney and New Attractions!

9.09.0 out of 10 rating
Wonderful
(14 reviews)
No Cleaning Fee! Luxury Villa Awaits! Close to Disney and New Attractions!
Davenport, FL
8% off
Price is NZ$3,938
NZ$3,938
NZ$563 per night
includes taxes & fees
Image gallery for 5Star Resort/Clean and Safe/Mins to Parks/WaterPark/Arcade/Bar/Gym/Golf/AC/WiFi

9.49.4 out of 10 rating
Exceptional
(101 reviews)
5Star Resort/Clean and Safe/Mins to Parks/WaterPark/Arcade/Bar/Gym/Golf/AC/WiFi
Davenport, FL
6% off
Price is NZ$6,716
NZ$6,716
NZ$959 per night
includes taxes & fees
Image gallery for Ultimate 10 Bed Luxury Retreat with Epic Playroom

9.49.4 out of 10 rating
Exceptional
(10 reviews)
Ultimate 10 Bed Luxury Retreat with Epic Playroom
Clermont, FL
8% off
Price is NZ$8,585
NZ$8,585
NZ$1,226 per night
includes taxes & fees
Image gallery for Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney

1010 out of 10 rating
Exceptional
(37 reviews)
Unforgettable Escape: Private Pool, Smart TV, Dreamy Resort, Moments from Disney
Kissimmee, FL
7% off
Price is NZ$2,975
NZ$2,975
NZ$425 per night
includes taxes & fees
Image gallery for Disney Dreams Villa Spacious 5 Bed 3 Bath Highland Reserve Near Disney Parks

1010 out of 10 rating
Exceptional
(21 reviews)
Disney Dreams Villa Spacious 5 Bed 3 Bath Highland Reserve Near Disney Parks
Davenport, FL
7% off
Price is NZ$2,894
NZ$2,894
NZ$413 per night
includes taxes & fees
Image gallery for Sunny Lake Reserve south facing pool lake view 2 master bed rooms w/en-suite

9.69.6 out of 10 rating
Exceptional
(76 reviews)
Sunny Lake Reserve south facing pool lake view 2 master bed rooms w/en-suite
Davenport, FL
7% off
Price is NZ$1,803
NZ$1,803
NZ$258 per night
includes taxes & fees
Image gallery for Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora

1010 out of 10 rating
Exceptional
(67 reviews)
Lake Vibes Only ~ Intimate Lake Cottage in Mount Dora
Mount Dora, FL
8% off
Price is NZ$2,678
NZ$2,678
NZ$383 per night
includes taxes & fees
Image gallery for 5BR/3 Stories Home/Balconies/Reunion Resort/Disney

9.09.0 out of 10 rating
Wonderful
(10 reviews)
5BR/3 Stories Home/Balconies/Reunion Resort/Disney
Kissimmee, FL
6% off
Price is NZ$2,746
NZ$2,746
NZ$392 per night
includes taxes & fees
Image gallery for Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins

9.69.6 out of 10 rating
Exceptional
(38 reviews)
Spacious upgraded 1st floor condo w/ Resort Amenities. Disney, less than 15 mins
Davenport, FL
7% off
Price is NZ$2,020
NZ$2,020
NZ$289 per night
includes taxes & fees
Image gallery for Emerald Island Resort Community,Gated 4 bedrooms 3 baths Heated Pool and Spa

9.49.4 out of 10 rating
Exceptional
(118 reviews)
Emerald Island Resort Community,Gated 4 bedrooms 3 baths Heated Pool and Spa
Kissimmee, FL
7% off
Price is NZ$2,520
NZ$2,520
NZ$360 per night
includes taxes & fees
Image gallery for Amazing 12Br 12Ba Twin Villas! Includes 2 private pools and 2 hot tubs!

8.88.8 out of 10 rating
Excellent
(5 reviews)
Amazing 12Br 12Ba Twin Villas! Includes 2 private pools and 2 hot tubs!
Davenport, FL
7% off
Price is NZ$11,092
NZ$11,092
NZ$1,585 per night
includes taxes & fees
Image gallery for Perfect family retreat mins to Disney and Universal in enchanting Champions Gate

9.69.6 out of 10 rating
Exceptional
(91 reviews)
Perfect family retreat mins to Disney and Universal in enchanting Champions Gate
Davenport, FL
6% off
Price is NZ$5,338
NZ$5,338
NZ$763 per night
includes taxes & fees
Image gallery for 10min To Disney, Private Pool, Security Gated, Luxury stay in Kissimmee Orlando

9.49.4 out of 10 rating
Exceptional
(94 reviews)
10min To Disney, Private Pool, Security Gated, Luxury stay in Kissimmee Orlando
Kissimmee, FL
7% off
Price is NZ$3,150
NZ$3,150
NZ$450 per night
includes taxes & fees
Image gallery for Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool

9.89.8 out of 10 rating
Exceptional
(126 reviews)
Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Kissimmee, FL
8% off
Price is NZ$3,973
NZ$3,973
NZ$568 per night
includes taxes & fees
Image gallery for Luxury large 6 Bed Villa, Pool and Spa. Make memories - 15 minutes from Disney

8.48.4 out of 10 rating
Very good
(132 reviews)
Luxury large 6 Bed Villa, Pool and Spa. Make memories - 15 minutes from Disney
Davenport, FL
7% off
Price is NZ$2,839
NZ$2,839
NZ$406 per night
includes taxes & fees
Image gallery for Luxury 8 Bedroom Villa, Good for 18 to 20, Pool/Spa

8.68.6 out of 10 rating
Excellent
(154 reviews)
Luxury 8 Bedroom Villa, Good for 18 to 20, Pool/Spa
Kissimmee, FL
7% off
Price is NZ$3,459
NZ$3,459
NZ$494 per night
includes taxes & fees
Image gallery for Reunion Resort - Near Theme Parks & Airport

9.69.6 out of 10 rating
Exceptional
(48 reviews)
Reunion Resort - Near Theme Parks & Airport
Kissimmee, FL
6% off
Price is NZ$1,718
NZ$1,718
NZ$245 per night
includes taxes & fees
Image gallery for Gus & Gan's Orlando Vacation Villa - Family Friendly 20 Mins From Disney Parks

9.69.6 out of 10 rating
Exceptional
(208 reviews)
Gus & Gan's Orlando Vacation Villa - Family Friendly 20 Mins From Disney Parks
Clermont, FL
7% off
Price is NZ$2,473
NZ$2,473
NZ$353 per night
includes taxes & fees
Image gallery for Upstay: Resort Oasis w/ Pool & Hot Tub Near Disney

9.89.8 out of 10 rating
Exceptional
(8 reviews)
Upstay: Resort Oasis w/ Pool & Hot Tub Near Disney
Kissimmee, FL
7% off
Price is NZ$4,397
NZ$4,397
NZ$628 per night
includes taxes & fees
Image gallery for 4BR Paradise Townhome | Private Pool | Resort Amenities | Discounts for 5+ Night Stays

9.69.6 out of 10 rating
Exceptional
(87 reviews)
4BR Paradise Townhome | Private Pool | Resort Amenities | Discounts for 5+ Night Stays
Kissimmee, FL
12% off
Price is NZ$2,855
NZ$2,855
NZ$408 per night
includes taxes & fees
Image gallery for NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~

8.88.8 out of 10 rating
Excellent
(12 reviews)
NEW OPENING! 5b4b Disney Themed Vacation Home w/Pool & BBQ ~12 min from Disney~
Kissimmee, FL
7% off
Price is NZ$3,025
NZ$3,025
NZ$432 per night
includes taxes & fees
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Find the best place to stay - Windermere Country Club
Wyndham Bonnet Creek - 1 Bedroom w/Full Kitchen - Disney with Lazy River!
Sleeps 4 · 1 bedroom · 1 bathroom
Epic Universe-Convention Center - 3 Bedrooms Apartment - Vista Cay Reserve
Sleeps 6 · 3 bedrooms · 2 bathrooms
Marriott's Cypress Harbour | Two-Bedroom Villa
Sleeps 8 · 2 bedrooms · 2 bathrooms
Luxury 8 Bedroom Villa, Good for 18 to 20, Pool/Spa
Sleeps 20 · 8 bedrooms · 5 bathrooms
8.68.6 out of 10
Excellentexcellent
154 reviews(154 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