Explore Windward Cay Golf Retreats
New
House
6 Bedrooms
5 Baths
14 Guests
3512 ft²
Private Pool
Hot Tub
Parking
Pool
US $505/Night
7 Nights - US $3,532
House
10.0Exceptional
(8 Reviews)
4 Bedrooms
3 Baths
12 Guests
1915.98 ft²
- Parking
- Pool
Spa
View
US $227/Night
7 Nights - US $1,586
Villa
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Pool
Kitchen
Internet
Child Friendly
US $1,122/Night
7 Nights - US $7,856
New
House
4 Bedrooms
3 Baths
12 Guests
1694 ft²
- Parking
- Kitchen
Air Conditioner- Internet
US $486/Night
7 Nights - US $3,399
Villa
10.0Exceptional
(7 Reviews)
6 Bedrooms
6 Baths
14 Guests
2830.91 ft²
Oceanfront
EV Charge Station- Parking
- Pool
US $324/Night
7 Nights - US $2,266
New
House
3 Bedrooms
2 Baths
6 Guests
1352 ft²
- Parking
- Pool
Balcony/Terrace- Kitchen
US $247/Night
7 Nights - US $1,730
Condo
- Florida
- ·
- Florida Central Atlantic Coast
- 8.11 mi to center
9.4Exceptional
(94 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
Ocean View
US $232/Night
7 Nights - US $1,624
Condo
- Florida
- ·
- Florida Central Atlantic Coast
- 8.32 mi to center
9.0Exceptional
(71 Reviews)
2 Bedrooms
2 Baths
7 Guests
1080 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $168/Night
7 Nights - US $1,176
Condo
- Florida
- ·
- Florida Central Atlantic Coast
- 8.23 mi to center
7.4Very Good
(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,095/Night
7 Nights - US $7,666
Luxury Places to Stay in Windward Cay
Over 10000+ Luxury Places to Stay in or Near Windward Cay
Villa
8.0Excellent
(2 Reviews)
5 Bedrooms
5 Baths
14 Guests
3000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
Unlock the Best Price
House
8.8Fabulous
(11 Reviews)
6 Bedrooms
5 Baths
17 Guests
3100 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
Unlock the Best Price
House
56 Bedrooms
56 Baths
26212 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $5,213/Night
7 Nights - US $36,494
House
56 Bedrooms
56 Baths
26228 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $4,457/Night
7 Nights - US $31,197
House
42 Bedrooms
42 Baths
19671 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,924/Night
7 Nights - US $27,467
House
10.0Exceptional
(1 Review)
42 Bedrooms
42 Baths
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,924/Night
7 Nights - US $27,467
House
10.0Exceptional
(1 Review)
42 Bedrooms
42 Baths
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,924/Night
7 Nights - US $27,467
House
10.0Exceptional
(1 Review)
42 Bedrooms
41 Baths
- Private Pool
- Hot Tub
- Parking
- Pool
US $3,924/Night
7 Nights - US $27,467
House
42 Bedrooms
42 Baths
19659 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $3,357/Night
7 Nights - US $23,497
Top-Rated Villas with a Pool in Windward Cay
Over 10000+ Top-Rated Private Villas with a Pool in or Near Windward Cay
House
10.0Exceptional
(271 Reviews)
3 Bedrooms
2 Baths
8 Guests
1797 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $144/Night
7 Nights - US $1,011
Condo
10.0Exceptional
(239 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $184/Night
7 Nights - US $1,289
Villa
- Orlando
- ·
- Lake Berkley
- 0.15 mi to center
10.0Exceptional
(222 Reviews)
4 Bedrooms
3 Baths
8 Guests
1750 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $250/Night
7 Nights - US $1,750
House
- Orlando
- ·
- Crystal Cove
- 0.18 mi to center
10.0Exceptional
(191 Reviews)
4 Bedrooms
3 Baths
9 Guests
2003 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $286/Night
7 Nights - US $2,000
Villa
10.0Exceptional
(164 Reviews)
6 Bedrooms
5 Baths
15 Guests
3275 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $476/Night
7 Nights - US $3,331
House
10.0Exceptional
(138 Reviews)
5 Bedrooms
5 Baths
12 Guests
33164 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $310/Night
7 Nights - US $2,167
House
10.0Exceptional
(137 Reviews)
5 Bedrooms
5 Baths
12 Guests
33164 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $291/Night
7 Nights - US $2,039
Apartment
10.0Exceptional
(116 Reviews)
3 Bedrooms
2 Baths
6 Guests
14305 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $199/Night
7 Nights - US $1,391
House
10.0Exceptional
(111 Reviews)
4 Bedrooms
3 Baths
10 Guests
1914 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $319/Night
7 Nights - US $2,235
Pet-Friendly Villas in Windward Cay
Over 2119+ Pet-Friendly Private Villas in or Near Windward Cay
House
7.4Very Good
(13 Reviews)
4 Bedrooms
3 Baths
9 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $314/Night
7 Nights - US $2,200
House
10.0Exceptional
(3 Reviews)
4 Bedrooms
4 Baths
10 Guests
1754.52 ft²
- Oceanfront
- Parking
- Pool
- Spa
US $330/Night
7 Nights - US $2,313
Apartment
1 Bedroom
1 Bath
- Parking
- Internet
Pet Friendly- Child Friendly
US $389/Night
7 Nights - US $2,721
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
10 Guests
1734 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $325/Night
7 Nights - US $2,273
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
11 Guests
1754.52 ft²
- Private Pool
Breakfast- Parking
- Pool
US $207/Night
7 Nights - US $1,449
New
House
9.4Exceptional
(30 Reviews)
4 Bedrooms
3 Baths
11 Guests
2000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $404/Night
7 Nights - US $2,826
New
Villa
9.4Exceptional
(28 Reviews)
5 Bedrooms
4 Baths
13 Guests
3200 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $365/Night
7 Nights - US $2,557
New
House
8.8Fabulous
(41 Reviews)
4 Bedrooms
3 Baths
12 Guests
1920 ft²
- Private Pool
- Parking
- Pool
- Kitchen
US $269/Night
7 Nights - US $1,884
House
8.8Fabulous
(20 Reviews)
7 Bedrooms
5 Baths
16 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $334/Night
7 Nights - US $2,338
Large Private Villas in Windward Cay
Over 8898+ Large Villas in or Near Windward Cay for Groups and Families
New
House
10.0Exceptional
(1 Review)
8 Bedrooms
5 Baths
18 Guests
3250 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $427/Night
7 Nights - US $2,988
House
10.0Exceptional
(6 Reviews)
15 Bedrooms
16 Baths
33 Guests
4262.51 ft²
- Parking
- Pool
- Spa
- View
US $925/Night
7 Nights - US $6,475
Villa
1 Bedroom
1 Bath
- Parking
- Pool
- Kitchen
- Internet
US $902/Night
7 Nights - US $6,316
New
Villa
9.6Exceptional
(23 Reviews)
3 Bedrooms
3 Baths
9 Guests
1914 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $294/Night
7 Nights - US $2,055
House
10.0Exceptional
(6 Reviews)
5 Bedrooms
4 Baths
15 Guests
2292.71 ft²
- Parking
- Pool
- Spa
- View
US $244/Night
7 Nights - US $1,708
House
9.6Exceptional
(5 Reviews)
4 Bedrooms
5 Baths
15 Guests
2996 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $589/Night
7 Nights - US $4,123
Villa
10 Bedrooms
8 Baths
20 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $883/Night
7 Nights - US $6,181
Villa
10 Bedrooms
8 Baths
20 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $801/Night
7 Nights - US $5,609
New
Villa
1 Bedroom
4 Baths
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $770/Night
7 Nights - US $5,393
Wheelchair Accessible Holiday Homes in Windward Cay
Over 1743+ Wheelchair Accessible Villas and Holiday Homes in or Near Windward Cay
Condo
- Florida
- ·
- Florida Central Atlantic Coast
- 8.12 mi to center
2 Bedrooms
2 Baths
6 Guests
1060 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $287/Night
7 Nights - US $2,007
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
2497.23 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $170/Night
7 Nights - US $1,190
Condo
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Parking
- Pool
- Kitchen
- Internet
US $576/Night
7 Nights - US $4,034
New
Apartment
- Florida
- ·
- Florida Central Atlantic Coast
- 8.13 mi to center
2 Bedrooms
2 Baths
6 Guests
1060 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $265/Night
7 Nights - US $1,858
House
10.0Exceptional
(1 Review)
7 Bedrooms
5 Baths
15 Guests
3293.76 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $527/Night
7 Nights - US $3,688
Condo
- Florida
- ·
- Florida Central Atlantic Coast
- 8.06 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
8 Guests
1400 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $414/Night
7 Nights - US $2,900
Condo
- Florida
- ·
- Florida Central Atlantic Coast
- 8.13 mi to center
9.4Exceptional
(8 Reviews)
3 Bedrooms
3 Baths
8 Guests
1400 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $413/Night
7 Nights - US $2,889
Condo
- Florida
- ·
- Florida Central Atlantic Coast
- 8.13 mi to center
9.0Exceptional
(125 Reviews)
3 Bedrooms
2 Baths
8 Guests
1253 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $183/Night
7 Nights - US $1,283
Condo
- Florida
- ·
- Florida Central Atlantic Coast
- 8.12 mi to center
8.0Excellent
(1 Review)
3 Bedrooms
3 Baths
6 Guests
1400 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $414/Night
7 Nights - US $2,900
Windward Cay Villas, Airbnb and Holiday Homes Under $200
Over 4132+ Windward Cay Private Villas, Airbnb and Holiday Homes Under $200
Condo
- Florida
- ·
- Florida Central Atlantic Coast
- 8.15 mi to center
2 Bedrooms
2 Baths
6 Guests
1072 ft²
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $181/Night
7 Nights - US $1,265
Apartment
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1184.03 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $197/Night
7 Nights - US $1,382
House
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $154/Night
7 Nights - US $1,078
New
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $163/Night
7 Nights - US $1,141
Apartment
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1184.03 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $171/Night
7 Nights - US $1,197
New
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $163/Night
7 Nights - US $1,141
New
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $163/Night
7 Nights - US $1,141
New
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $163/Night
7 Nights - US $1,141
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $163/Night
7 Nights - US $1,141
Instantly Bookable Villa Rentals in Windward Cay
Over 10439+ Instantly Bookable Private Villas in or Near Windward Cay
New
House
3 Bedrooms
2 Baths
8 Guests
- Internet
- Child Friendly
- Laundry
Security/Safety
US $412/Night
7 Nights - US $2,883
House
3 Bedrooms
2 Baths
6 Guests
107.64 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $100/Night
7 Nights - US $700
House
1 Bedroom
1 Bath
- Child Friendly
US $5,150/Night
7 Nights - US $36,050
New
House
1 Bedroom
3 Baths
10 Guests
1914 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $319/Night
7 Nights - US $2,236
New
Hotel
- Florida
- ·
- Florida Central Atlantic Coast
- 8.07 mi to center
9.4Exceptional
(37 Reviews)
4 Baths
1800 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $349/Night
7 Nights - US $2,441
House
10.0Exceptional
(9 Reviews)
5 Bedrooms
4 Baths
10 Guests
2500 ft²
- Parking
- Pool
- Ocean View
- View
US $246/Night
7 Nights - US $1,724
New
House
- Orlando
- ·
- Lake Berkley
- 0.11 mi to center
10.0Exceptional
(7 Reviews)
7 Bedrooms
7 Baths
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $543/Night
7 Nights - US $3,803
New
House
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
US $245/Night
7 Nights - US $1,715
Villa
- Orlando
- ·
- Lake Berkley
- 0.09 mi to center
10.0Exceptional
(3 Reviews)
5 Bedrooms
4 Baths
10 Guests
2500 ft²
- Parking
- Pool
- Ocean View
- View
US $246/Night
7 Nights - US $1,724
Book a Last Minute Place to Stay in Windward Cay
About Windward Cay Vacation Rentals
Explore over 16316 golf accommodation rentals in Windward Cay. From luxurious golf villas to cozy golf cabins, golf resorts, and exclusive golf hotels, each offers premium amenities designed for families, groups, and golf enthusiasts. Enjoy exceptional comfort and a one-of-a-kind golf experience with these incredible accommodations. Perfect for tranquil golf escapes, relaxing retreats, or golf-inspired getaways, these properties provide style and comfort in Windward Cay.
Looking for last-minute deals or the best offers on golf villas, golf cabins, golf resorts, and other golf retreats? StayAndPlay makes it easy to compare options in Windward Cay. Choose from spacious family-friendly stays, charming golf escapes, or luxurious golf retreats tailored for ultimate relaxation and play.
Find spacious family-friendly golf accommodations, golf cottage, or luxurious golf villas—all designed for maximum comfort and convenience during your visit.On average, golf accommodation rentals in Windward Cay offer approximately 1656.1 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning golf course surroundings.
The average nightly rate for golf accommodation rentals in Windward Cay typically ranges around US $389.
StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in Windward Cay. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in golf with us.
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Top Golf Accommodation Types in Windward Cay
| Type | Count |
|---|---|
| Vacation Homes | 10074 |
| Villas | 2152 |
| Holiday Apartments | 1995 |
| Cottages | 73 |
| Ski Chalet Rentals | 18 |
| Others | 11 |
| B&B | 9 |
| Cabin Rentals | 3 |
Use these Quick Filters to Find a Vacation Rental in Windward Cay
★ Pro Tip: StayAndPlay simplifies your search for the best golf accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore golf villas, cozy golf cabins, golf hotels, and golf resorts. Filter by availability, pricing, cancellation options, and amenities to discover the ideal golf retreat in Windward Cay.
Weather in Windward Cay, FL
View the weather forecast for Windward Cay before booking your Windward Cay Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Windward Cay?
What are the best golf resorts, luxury villas, and vacation rentals in Windward Cay?
Looking for a place to stay in Windward Cay? Explore these highly-rated golf vacation rentals for a one-of-a-kind golf retreat, where you can relax, unwind, and get ready to play your best game:
- BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY. FULLY EQUIPED
- ⭐SALE! AUG 1-13 5 STAR CONDO*PREMIER HOST*GREAT PRICE&CLOSE TO ALL ATTRACTIONS⭐
- Delightful modern 4 bed, 3 bath villa with private pool/spa and lake view.
- 5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area
- Beautiful Home, 6-Bdrms, 5-Baths, Very Near Disney, Private Pool and Spa
- 🏝️ 5BR/5BA Home w/Private Pool & Spa, Themed Kids’ Rooms & Resort Water Park | Storey Lake Near Disney
- 🏝️ 5BR/5BA Home w/Private Pool & Spa, Themed Kids’ Rooms & Resort Fun | Storey Lake Near Disney
- Spacious End-Unit Condo | Modern Open Floor Plan w/Elegant Décor & Full Comfort | Minutes to Disney
- Great Location! Disney-Universal-Kid Gear-Free Pool Heat-Lake view- Family Fun
- Awesome Daydreamer Home, Pool, Waterpark, Slides, Lazy River, near all Parks
How many golf stays with private pools are available in Windward Cay?
Find exceptional golf retreats with private pools near Windward Cay on StayAndPlay. Relax in serene golf vacation rentals with exclusive pool access and picturesque golf course views. Whether it's a spacious golf villa or a secluded golf cabin, these properties offer the perfect blend of luxury and relaxation, so you can focus on your game.
- Amazing Modern Home 10BR/5BH - Pool/Spa/Game Room
- 4826 LL - Storey Lake Dream 4BR Pool Home Near Disney
- Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
- Last Minute Disney! Private Pool, Hot Tub & Themed Bedrooms. Book Now! #17198
What are the top-rated golf retreats in Windward Cay for family stays?
Searching for a family-friendly golf retreat in Windward Cay? Explore these top-rated options, each loved by families and groups who have stayed in Windward Cay:
- Luxury Resort Condo, close to Disney, Great for Families
- Stunning Townhome with Private Pool - Storey Lake - 5021 WW
- Fireworks @ Night -storey Lake By Shine Villas 709 2 Bedroom Apts
How many StayAndPlay golf vacation rentals are available in Windward Cay?
StayAndPlay, as of 2026, features over 16316 unique golf villas, golf hotels, golf resorts, and more in Windward Cay. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.
By 2026, StayAndPlay has curated over 16316 stunning properties in Windward Cay, sourced from trusted platforms. Plan your next golf trip now.
For 2026, StayAndPlay provides access to over 16316 premier golf accommodations in Windward Cay. Find your ideal golf-retreat and play your best game with StayAndPlay.
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