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24,182 Houses
Villa in Windward Cay, Kissimee, Orlando, Florida, USA
Kissimmee / Winward Cay
3 8 7 nights min
- 3 bedrooms
- sleeps 8
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$80
Price per night from
$80
Florida Lets A Dream
Kissimmee / Winward Cay
3 8 7 nights min
- 3 bedrooms
- sleeps 8
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$104
Price per night from
$104
Florida Villa Dreams Come True
Kissimmee / Winward Cay
3 8 7 nights min
- 3 bedrooms
- sleeps 8
- 7 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$104
Price per night from
$104
Great rentals within 20 miles that match your search
Distance approx 9.65 km from Winward Cay
Emerald Island 7 bedroom villa 4 miles from Disney
Central Florida / Kissimmee
7 16 6 nights min
- 7 bedrooms
- sleeps 16
- 6 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$573
Price per night from
$573
Distance approx 14.62 km from Winward Cay
Sapphire Skies Vacation Villa
Lake County / Clermont
4 8 4 nights min
- 4 bedrooms
- sleeps 8
- 4 nights min
- Swimming pool
- Child Friendly
- Car not necessary
Price per night from
$171
Responds fast!
avg. 3 hours 56 minutes
Price per night from
$171
Distance approx 8.56 km from Winward Cay
Certificate of Excellence
Fabulous Beautiful Townhome Vista Cay Orlando
Central Florida / Orlando
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Certificate of Excellence
Price per night from
$194
Responds fast!
avg. 2 hours 16 minutes
Price per night from
$194
Distance approx 11.92 km from Winward Cay
Woodville - in a beautiful location near Disney
Central Florida / Davenport
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$149
Responds fast!
avg. 1 hour 41 minutes
Price per night from
$149
Distance approx 11.89 km from Winward Cay
Exclusive Home Within High Grove Gated Community
Clermont / High Grove
5 10 min stay varies
- 5 bedrooms
- sleeps 10
- min stay varies
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Price per night from
$172
Price per night from
$172
Distance approx 9.47 km from Winward Cay
Rider's Castle
Kissimmee / Emerald Isle Kissimmee
7 14 min stay varies
- 7 bedrooms
- sleeps 14
- min stay varies
- Nearest beach 280 mi
- Swimming pool
- Child Friendly
Price per night from
$287
Responds fast!
avg. 3 hours 13 minutes
Price per night from
$287
Distance approx 8.86 km from Winward Cay
Stunning 5 bed property with private south facing extended deck and spa overlook
Central Florida / Davenport
5 12 min stay varies
- 5 bedrooms
- sleeps 12
- min stay varies
- Ask about children
Price per night from
$155
Price per night from
$155
Distance approx 15.61 km from Winward Cay
Dennis Souther Dunes House
Central Florida / Haines City
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$94
Price per night from
$94
Distance approx 5.32 km from Winward Cay
Wyndham Bonnet Creek Resort - Close to Disney 2 BD - 2 BA Deluxe Suite
Central Florida / Orlando
2 8 7 nights min
- 2 bedrooms
- sleeps 8
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$328
Responds fast!
avg. 35 minutes
Price per night from
$328
Distance approx 7.85 km from Winward Cay
Reunion Resort Condo Overlooking Golf Course!
Central Florida / Kissimmee
3 10 min stay varies
- 3 bedrooms
- sleeps 10
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$166
Responds fast!
avg. 19 minutes
Price per night from
$166
Distance approx 11.96 km from Winward Cay
Fabulous 4 bed villa with south facing private pool and spa
Central Florida / Davenport
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Ask about children
Price per night from
$138
Price per night from
$138
Distance approx 12.02 km from Winward Cay
Bright, Spacious, Immaculate Villa, Large Pool/Spa
Central Florida / Davenport
5 10 5 nights min
- 5 bedrooms
- sleeps 10
- 5 nights min
- Child Friendly
Price per night from
$172
Price per night from
$172
Distance approx 11.77 km from Winward Cay
Downing Florida House 402
Central Florida / Davenport
5 11 min stay varies
- 5 bedrooms
- sleeps 11
- min stay varies
- Swimming pool
- Car not necessary
- Air conditioning
Price per night from
$196
Responds fast!
avg. 3 hours 35 minutes
Price per night from
$196
Distance approx 1.62 km from Winward Cay
***NEW LISTING*** Wyndham Star Island
Florida / Old Town
2 8 3 nights min
- 2 bedrooms
- sleeps 8
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$400
Responds fast!
avg. 2 hours 39 minutes
Price per night from
$400
Distance approx 15.47 km from Winward Cay
South Beach Villa
Central Florida / Haines City
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$162
Price per night from
$162
Distance approx 11.55 km from Winward Cay
My Disney Dream Home
Central Florida / Four Corners
5 12 3 nights min
- 5 bedrooms
- sleeps 12
- 3 nights min
- Child Friendly
Price per night from
$144
Price per night from
$144
Distance approx 15.59 km from Winward Cay
Martin's Southern Dunes House
Central Florida / Haines City
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$123
Price per night from
$123
Distance approx 8.04 km from Winward Cay
2 bedroom for share in townhouse
Central Florida / Loughman
2 4 1 night min
- 2 bedrooms
- sleeps 4
- 1 night min
- Nearest beach 50 mi
- Swimming pool
- Child Friendly
Price per night from
$58
Price per night from
$58
Distance approx 10.84 km from Winward Cay
3217PP
Central Florida / Four Corners
5 12 min stay varies
- 5 bedrooms
- sleeps 12
- min stay varies
- Swimming pool
- Ask about children
Price per night from
$189
Price per night from
$189
Distance approx 11.97 km from Winward Cay
South facing pool and spa with conservation view close to Disney
Central Florida / Davenport
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Ask about children
Price per night from
$138
Price per night from
$138
Distance approx 2.38 km from Winward Cay
3189 Tocoa
Central Florida / Kissimmee
4 8 3 nights min
- 4 bedrooms
- sleeps 8
- 3 nights min
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$149
Price per night from
$149
Distance approx 9.77 km from Winward Cay
ENCHANTED DISNEY RESORT NEAR
Central Florida / Four Corners
3 7 2 nights min
- 3 bedrooms
- sleeps 7
- 2 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$115
Price per night from
$115
Distance approx 12.69 km from Winward Cay
Luxurious Four Bedroom Villa on the Prestigious Highgate Park Development, Sleep
Central Florida / Davenport
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Ask about children
Price per night from
$138
Price per night from
$138
Distance approx 7.72 km from Winward Cay
Westgate Town Center-3BR 3BA 7 Ngt Max Lux Resort
Central Florida / Kissimmee
3 12 7 nights min
- 3 bedrooms
- sleeps 12
- 7 nights min
- Child Friendly
- Air conditioning
Price per night from
$315
Price per night from
$315
Distance approx 10.05 km from Winward Cay
Beautiful 4BR 3bth Champions Gate Townhouse with Private Splash Pool
Central Florida / Orlando
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$147
Responds fast!
avg. 2 hours 12 minutes
Price per night from
$147
Distance approx 11.19 km from Winward Cay
My Disney Villa
Kissimmee / Calabria, Orlando
5 10 min stay varies
- 5 bedrooms
- sleeps 10
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$275
Responds fast!
avg. 3 hours 30 minutes
Price per night from
$275
Distance approx 7.78 km from Winward Cay
Superb 6 bedroom home, private pool and spa, free pool heat for certain dates
Central Florida / Four Corners
6 12 min stay varies
- 6 bedrooms
- sleeps 12
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$111
Price per night from
$111
Distance approx 4.06 km from Winward Cay
Certificate of Excellence
Fantastic Kissimmee Home and only 20 min
Kissimmee / Trafalgar Village
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 80 mi
- Swimming pool
Certificate of Excellence
Price per night from
$97
Responds fast!
avg. 1 hour 46 minutes
Price per night from
$97
Distance approx 12.25 km from Winward Cay
Villa Tropico near Disney - FREE cancellation
Central Florida / Davenport
3 7 4 nights min
- 3 bedrooms
- sleeps 7
- 4 nights min
- Ask about children
- Air conditioning
Price per night from
$137
Price per night from
$137
Distance approx 10.06 km from Winward Cay
New 8BR 6bth Luxury Resort home w/private south facing pool and spa
Central Florida / Orlando
8 16 min stay varies
- 8 bedrooms
- sleeps 16
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$336
Responds fast!
avg. 2 hours 12 minutes
Price per night from
$336
Distance approx 10.06 km from Winward Cay
Lovely 5BR 3Bth Home with Private Pool, Spa and Pool Table, 15 Minutes to Disney
Central Florida / Orlando
5 10 5 nights min
- 5 bedrooms
- sleeps 10
- 5 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$176
Responds fast!
avg. 2 hours 12 minutes
Price per night from
$176
Distance approx 13.23 km from Winward Cay
Sunrise Orlando Villa
Lake County / Clermont
4 9 min stay varies
- 4 bedrooms
- sleeps 9
- min stay varies
- Child Friendly
Price per night from
$105
Price per night from
$105
Distance approx 10.05 km from Winward Cay
Chic 6 bedroom 5.5 bath Watersong Resort home from $135nt
Central Florida / Orlando
6 12 min stay varies
- 6 bedrooms
- sleeps 12
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$178
Responds fast!
avg. 2 hours 12 minutes
Price per night from
$178
Distance approx 12.27 km from Winward Cay
Beautiful Orlando Villa "Mags Den" Calabay Parc
Central Florida / Davenport
4 8 5 nights min
- 4 bedrooms
- sleeps 8
- 5 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$148
Price per night from
$148
Distance approx 10.71 km from Winward Cay
Brand New Disney Vacation Home,6BR,5BA,Pool/Spa
Central Florida / Kissimmee
6 14 3 nights min
- 6 bedrooms
- sleeps 14
- 3 nights min
- Swimming pool
- Ask about children
- Air conditioning
Price per night from
$228
Price per night from
$228
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.