Orlando Vacation Rentals - Vacation Rentals in Windward Cay

Cozzy Townhouse! 925PTC-SVH From US $100
         

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Lakeview Home w/Private Pool & Free Water Park! From US $640
         

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10.0 (3 Reviews)
Cottage
  • Air Conditioner
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  • Pool

Luxury Places to Stay in Windward Cay

Over 10000+ Luxury Places to Stay in or Near Windward Cay
6 Bed villa close to disney From US $61,189
         

10.0 (1 Review)
House
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  • Pool
  • TV
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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8.4 (30 Reviews)
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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 $260
         

Pet-Friendly Vacation Rentals in Windward Cay

Over 2067+ Pet-Friendly Vacation Rentals in or Near Windward Cay
Vacation rental with a touch of Class! From US $153
         

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 $667
         

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

9.8 (24 Reviews)
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  • Pet Friendly
4 Bedroom Home and Private Pool, pets considered From US $222
         

8.4 (49 Reviews)
House
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  • Pet Friendly
Storey Lake Resort 4 Bedroom Townhome Pet Friendly From US $294
         

9.4 (9 Reviews)
House
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7 Bedroom Luxury Home , Sleeps 16 From US $365
         

9.0 (51 Reviews)
House
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  • Pet Friendly

Large Vacation Homes & Villas in Windward Cay

Over 8862+ 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)
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2780 Bookmark Drive From US $970
         

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10.0 (2 Reviews)
Villa
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Wheelchair Accessible Vacation Homes in Windward Cay

Over 1722+ Wheelchair Accessible Vacation Homes in or Near Windward Cay
Vacation Meadows - Storey Lake By Shine Villas 710 2 Bedroom Apts From US $541
         

Charming Holiday Condo, Only 7 min to Disney From US $291
         

9.8 (63 Reviews)
Apartment
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Amazing stay/Waterpark/Near Disney From US $317
         

7.2 (5 Reviews)
Condo
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Family Fun: Condo near Theme Parks & Pools! From US $287
         

9.8 (11 Reviews)
Condo
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Windward Cay Vacation Rentals and Airbnb Places to Stay Under $200

Over 4478+ Windward Cay Vacation Rentals and Airbnb Places to Stay Under $200
Country Feel,Private Pool,Spa, Game Room From US $187
         

9.6 (31 Reviews)
House
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  • Pool
3BR Apartment - Great Location Super Comfort From US $140
         

10.0 (1 Review)
Apartment
  • Pool
  • Wheelchair Accessible
  • Balcony/Terrace
Family Resort by Disney, Roomy 2BR+Loft & 5 Pools! From US $177
         

9.8 (77 Reviews)
Condo
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Exquisite Destination. Bay Vista From US $181
         

9.6 (267 Reviews)
House
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Family Resort near Disney, 3BR+Loft & 5 Fun Pools! From US $190
         

9.4 (47 Reviews)
Condo
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  • Pool
Beautiful apartment 7 pax, very close to Disney! From US $155
         

9.4 (42 Reviews)
Apartment
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  • Pool

Instantly Bookable Vacation Homes in Windward Cay

Over 10225+ Instantly Bookable Vacation Homes in or Near Windward Cay
Splendid 3 Bed Villa in Windward Cay From US $178
         

10.0 (24 Reviews)
Villa
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  • Pool
5 Bedrooms/5 Bathrooms/Sonoma (2669 CA) From US $450
         

10.0 (4 Reviews)
House
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  • Parking
  • Pool
Cozy Family 4-Bedroom Bella Vida Home Near Disney World From US $293
         

Luxury Townhouse w/Free Waterpark & Pools 10 Min to Disney From US $259
         

Close to Disney - shabby chic style villa with private pool! From US $404
         

9.4 (120 Reviews)
Villa
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  • Child Friendly

About Windward Cay Vacation Rentals

With more than 16147 Windward Cay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Orlando Vacationrentals 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 Orlando Vacationrentals 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 1706.58 ft² on average, with prices averaging $398 a night.

Orlando Vacationrentals 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
Vacation Homes 9914
Villas 2091
Holiday Apartments 1965
Hotels with Suites 243
Resorts 169
Cottages 68
Ski Chalet Rentals 18
Others 11
B&B 7
Cabin Rentals 3
Hostels 2

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

Pro Tip: Orlando Vacationrentals makes it easy to compare the best listings on Orlando Vacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Orlando Vacationrentals 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


Windward Cay Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Windward Cay?
How many vacation rentals are available in Windward Cay?

Currently, the total number of properties listed in 2026 is over 16147 in the Windward Cay area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windward Cay.