Pirate Cove Cottages - Vacation Rentals in Windward Cay

5 miles from Disney & Universal! From US $103
         

10.0 (13 Reviews)
Cottage
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New! Family cottage near Disney-Sleep 6 From US $134
         

10.0 (1 Review)
House
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Lakeview Home w/Private Pool & Free Water Park! From US $640
         

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10.0 (3 Reviews)
Cottage
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MAGICAL VACATION From US $140
         

10.0 (2 Reviews)
Cottage
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Charming 2-bedroom cottage in Kissimmee From US $222
         

10.0 (1 Review)
Cottage
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Famiy friendly! Premier Lakeview Stylish Home From US $203
         

10.0 (1 Review)
Cottage
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  • Pet Friendly
Family-Friendly Cottage Near Orlando’s Top Attractions From US $203
         

Luxury Places to Stay in Windward Cay

Over 10000+ Luxury Places to Stay in or Near Windward Cay
Runaway Beach Club Condo near Disney From US $14,848
         

6BR Luxury Home w Private Pool & BBQ From US $5,900
         

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10BR - Family Home Near Disney with Pool & BBQ From US $5,900
         

6BR Luxury Home with Private Pool and BBQ From US $5,900
         

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8.3 (31 Reviews)
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Windward Cay

Over 10000+ Top-Rated Vacation Rentals with a Pool in or Near Windward Cay
Conservation View - Hot Tub - Free Pool Heat - Very Private From US $332
         

Pet-Friendly Vacation Rentals in Windward Cay

Over 1840+ Pet-Friendly Vacation Rentals in or Near Windward Cay
Vacation rental with a touch of Class! From US $148
         

9.6 (64 Reviews)
House
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  • Pet Friendly
Home With Private Pool & Activities, Near Disney! From US $216
         

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7.0 (1 Review)
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Jasmine 4 Bedrooms From US $744
         

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10.0 (1 Review)
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TOWNHOUSE NEAR DISNEY! From US $114
         

9.8 (24 Reviews)
House
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  • Pet Friendly
4 Bedroom Home and Private Pool, pets considered From US $230
         

8.2 (47 Reviews)
House
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  • Pet Friendly
Storey Lake Resort 4 Bedroom Townhome Pet Friendly From US $361
         

9.4 (9 Reviews)
House
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  • Pet Friendly
7 Bedroom Luxury Home , Sleeps 16 From US $313
         

9.0 (48 Reviews)
House
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  • Pet Friendly

Large Vacation Homes & Villas in Windward Cay

Over 8249+ Large Vacation Homes & Villas in or Near Windward Cay
Multi Resorts at Fantasy World From US $150
         

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7.4 (19 Reviews)
House
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Splendid 3 Bed Villa in Windward Cay From US $178
         

10.0 (24 Reviews)
Villa
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  • Pool

Wheelchair Accessible Vacation Homes in Windward Cay

Over 1685+ Wheelchair Accessible Vacation Homes in or Near Windward Cay
SUMMER SALE! Storey Lake 3BDRM From US $241
         

10.0 (2 Reviews)
Apartment
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Relaxing DisneyRoom/Clubhouses/Waterpark From US $206
         

8.6 (15 Reviews)
Condo
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Charming Holiday Condo, Only 7 min to Disney From US $197
         

9.8 (62 Reviews)
Apartment
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Amazing stay/Waterpark/Near Disney From US $206
         

7.2 (5 Reviews)
Condo
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  • Pool

Windward Cay Varoom and Airbnb Places to Stay Under $200

Over 4449+ Windward Cay Varoom and Airbnb Places to Stay Under $200
Cozzy Townhouse! 925PTC-SVH From US $100
         

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3BR Apartment - Great Location Super Comfort From US $140
         

10.0 (1 Review)
Apartment
  • Pool
  • Wheelchair Accessible
  • Accessibility
Special rates available in Sep and Oct of 2025 From US $172
         

9.4 (131 Reviews)
Villa
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Family Resort by Disney, Roomy 2BR+Loft & 5 Pools! From US $176
         

9.8 (77 Reviews)
Condo
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  • Pool
Beautiful apartment 7 pax, very close to Disney! From US $137
         

9.4 (40 Reviews)
Apartment
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  • Pool

Instantly Bookable Vacation Homes in Windward Cay

Over 9539+ Instantly Bookable Vacation Homes in or Near Windward Cay
5 Bedrooms/5 Bathrooms/Sonoma (2669 CA) From US $450
         

10.0 (4 Reviews)
House
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Country Feel,Private Pool,Spa, Game Room From US $221
         

9.6 (30 Reviews)
House
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  • Pool

About Windward Cay Vacation Rentals

With more than 65 Windward Cay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Piratecovecottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windward Cay.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Piratecovecottages Windward Cay, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windward Cay. Places to stay near Windward Cay are 151.27 ft² on average, with prices averaging $255 a night.

Piratecovecottages makes it easy and safe to find and compare vacation rentals in Windward Cay with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windward Cay

Type Count
Cottages 58
Resorts 4
Vacation Homes 3

Use these Quick Filters to Find a Vacation Rental in Windward Cay

Pro Tip: Piratecovecottages makes it easy to compare the best listings on Piratecovecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Piratecovecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windward Cay.

Weather in Windward Cay

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

Complexes around Windward Cay, FL