Find 5 Star Hotels in Windward Cay, FL from $104
Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Be picky
Search almost a million properties worldwide
Check availability on Windward Cay 5 Star Hotels
Compare Windward Cay 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
9.2 out of 10, Wonderful, (332)
$329 nightly
The price is $370
Sep 14 - Sep 15
Total with taxes and fees

Conrad Orlando at Evermore
Conrad Orlando at Evermore
9.6 out of 10, Exceptional, (274)
$475 nightly
The price is $535
Sep 28 - Sep 29
Total with taxes and fees

The Ritz-Carlton Orlando, Grande Lakes
The Ritz-Carlton Orlando, Grande Lakes
9.2 out of 10, Wonderful, (1006)
$431 nightly
The price is $485
Sep 14 - Sep 15
Total with taxes and fees

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort
9.6 out of 10, Exceptional, (867)
$945 nightly
The price is $1,063
Sep 1 - Sep 2
Total with taxes and fees

ette hotel
ette hotel
9.8 out of 10, Exceptional, (330)
$277 nightly
The price is $315
Sep 1 - Sep 2
Total with taxes and fees

Reunion Resort & Golf Club
Reunion Resort & Golf Club
8.8 out of 10, Excellent, (1384)

Encore Resort and Water Park at Reunion by Rentyl
Encore Resort and Water Park at Reunion by Rentyl
8.4 out of 10, Very Good, (1009)
$658 nightly
The price is $747
Sep 9 - Sep 10
Total with taxes and fees

Stunning 4Bd With Pool At Storey Lake Resort 4821
Stunning 4Bd With Pool At Storey Lake Resort 4821
8.0 out of 10, Very Good, (2)
Save an average of 15% on thousands of hotels when you're signed in
Explore similar 4-star hotels
Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Windward Cay.

DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd, Orlando, FL
$93 nightly
The price is $104 total per night from Sep 10 to Sep 11
$104 total
Sep 10 - Sep 11
Total with taxes and fees
8.2/10 Very Good! (6,587 reviews)
Still don't see what you're looking for?
See all properties in Windward Cay.
You can also use these popular filters to refine your search.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Windward Cay Hotel Reviews
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Orlando Hotels
- Hotels near Walt Disney World® Resort
- Kissimmee Hotels
- Hotels near Universal Studios Florida
- Hotels near Seasons
- Hotels near Royal Palm Bay
- Hotels near Medieval Times
- Hotels near Crystal Cove
- Hotels near Kissimmee Go-Karts
- Hotels near Bellavida
- Hotels near Chatham Park
- Hotels near Capone's Dinner Show
- Hotels near Lake Berkley
- Hotels near Veranda Palms
- Hotels near Pirate's Island Adventure Golf
- Hotels near Bass Lakes Estates
- Hotels near 192 Flea Market
- Hotels near Congo River Golf
- Hotels near Lake Cecile
- Hotels near The Hamlets
- Hotels near Osceola County Welcome Center and History Museum
- Hotels near Indian Point
- Hotels near AMF Bowling Center
- Hotels near Give Kids the World Village
- Hotels near Venetian Bay Villages
- Hotels near Creekside
- Hotels near Osceola Square Mall
- Hotels near Kissimmee Air Museum
- Hotels near Florida Technical College
- Hotels near Museum of Military History
- Hotels near Eagle Pointe South
- Hotels near Skate Reflections
- Hotels near Disney SpringsTM
- Hotels near Liberty Village
- Hotels near Orlando Intl.
- Hotels near Kissimmee Gateway
- Flights to Orlando
- Flights to Florida
- Flights from New York (JFK) to Orlando (MCO)
- Flights from Kissimmee Gateway
- Flights from Orlando (MCO) to Kissimmee (ISM)
- Flights from Miami (MIA) to Kissimmee (ISM)
- Flights from New York (JFK) to Kissimmee (ISM)
- Flights from Atlanta (ATL) to Kissimmee (ISM)
- Flights from Boston (BOS) to Kissimmee (ISM)
- Flights from Fort Lauderdale (FLL) to Kissimmee (ISM)
- Flights from Tampa (TPA) to Kissimmee (ISM)
- Flights from Philadelphia (PHL) to Kissimmee (ISM)
- Flights from Chicago (ORD) to Kissimmee (ISM)
- Flights from Charlotte (CLT) to Kissimmee (ISM)
- Flights from Jacksonville (JAX) to Kissimmee (ISM)
- Flights from Raleigh (RDU) to Kissimmee (ISM)
- Flights from Dallas (DFW) to Kissimmee (ISM)
- Flights from Sarasota (SRQ) to Kissimmee (ISM)
- Flights from Detroit (DTW) to Kissimmee (ISM)
- Flights from Houston (IAH) to Kissimmee (ISM)
- Flights from Baltimore (BWI) to Kissimmee (ISM)
- Flights from Fort Myers (RSW) to Kissimmee (ISM)
- Flights from Savannah (SAV) to Kissimmee (ISM)
- Flights from Richmond (RIC) to Kissimmee (ISM)
- Flights from Salt Lake City (SLC) to Kissimmee (ISM)
- Flights from Minneapolis (MSP) to Kissimmee (ISM)
- Flights from Melbourne (MLB) to Kissimmee (ISM)
- Flights from Panama City (ECP) to Kissimmee (ISM)
- Flights from New Orleans (MSY) to Kissimmee (ISM)
- Flights from Buffalo (BUF) to Kissimmee (ISM)
- Flights from Washington (DCA) to Kissimmee (ISM)
- Flights from Norfolk (ORF) to Kissimmee (ISM)
- Flights from Los Angeles (LAX) to Kissimmee (ISM)
- Flights from Phoenix (PHX) to Kissimmee (ISM)
- Flights from Pittsburgh (PIT) to Kissimmee (ISM)
- Flights from Hartford (BDL) to Kissimmee (ISM)
- Flights from Cleveland (CLE) to Kissimmee (ISM)
- Flights from Columbia (CAE) to Kissimmee (ISM)
- Walt Disney World® Resort
- Medieval Times
- Kissimmee Go-Karts
- Capone's Dinner Show
- 192 Flea Market
- Congo River Golf
- Lake Cecile
- Osceola County Welcome Center and History Museum
- AMF Bowling Center
- Give Kids the World Village
- Osceola Square Mall
- Kissimmee Air Museum
- Museum of Military History
- Skate Reflections
- Car rental Orlando Airport (MCO)
- Car rentals near Orlando
- Car rentals near Medieval Times
- Car rentals near Kissimmee Go-Karts
- Car rentals near 192 Flea Market
- Car rentals near Give Kids the World Village
- Car rentals near Kissimmee
- Car rentals near Skate Reflections
- Car rental Orlando Airport (ISM)
- Enterprise Rental Cars in Kissimmee Gateway
- Fox Rental Cars Rental Cars in Kissimmee Gateway
- National Car Rental Rental Cars in Kissimmee Gateway