We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
View map
Sponsored by:
Clear all
Your Selections
  Free Wifi Beach Luxury City Centre Mid-range Breakfast included Pool Romantic Best Value Free Parking Resort hotel Trendy Boutique Family-friendly Charming Quiet Restaurant Pets Allowed Suites Kitchenette Spa Bar/Lounge Airport Transportation Fitness centre Quaint Room Service Business Classic Green & up Internet & up Air Conditioning & up Non-Smoking Hotel Concierge Independent Hotels Clean Hotels Hotels with Restaurants Quiet Hotels Suite Hotels Hotels with Bars Hotels with Balconies Modern Hotels Charming Hotels Hotels with Free Wifi Beach Resorts Downtown Hotels City Centre Hotels Business services Hotels with Hot Tubs Meeting room Hotels with Jacuzzi Honeymoon Hotels Boutique Hotels Hotels with Complimentary Breakfast Safe Hotels Hotels with Shuttle Romantic Boutique Hotels Spring Break Hotels Hotels with Room Service Reduced mobility rooms Budget Hotels Wedding Hotels Cheap Hotels Couples Hotels Quiet Resorts Suite Resorts Unique Hotels Family Resorts Party Hotels Spa Hotels Spa Resorts Luxury Resorts Wedding Resorts Luxury Boutique Hotels Boutique Spa Hotels Spring Break Resorts Hotels with Kitchenette Historic Hotels Boardwalk Resorts Hotels with Private Beach Resorts with Jacuzzi Fishing Resorts Oceanfront Hotels Boutique Resorts Unique Resorts Duval Street Honeymoon Resorts Couples Resorts Heritage Hotels Themed Hotels Diving Resorts Condo Resorts Luxury Spa Hotels The Ernest Hemingway Home and Museum Mallory Square Luxury Spa Resorts Beach Motels Luxury Beach Resorts Hotels with Villas Boardwalk Hotels Condo Hotels Timeshare Resorts Hyatt Holiday Club Luxury Beach Hotels Hotels with Infinity Pools Cheap Resorts Affordable Hotels Affordable Resorts Romantic Bed and Breakfast Romantic Resorts Apartment Hotels $ $$ $$$ $$$$ Waldorf Astoria Fairfield Inn Adults Only and Adult Friendly Hotels Ibis Singles Hotels Sheraton Hotels with Smoking Rooms Hilton Garden Inn Hotels With Entertainment Courtyard Hyatt Marriott Autograph Collection All Inclusive Hotels Luxury Family Hotels Timeshare Rentals All Inclusive Resorts Best Western Plus Marriott Golf Resorts Crowne Plaza Best Western Health Resorts Any Distance from Key West Sailing Adventure
Price per night
Enter dates & see best prices
to
Amenities
More
Amenities
Location
(reset)
Any Distance
from
Traveller Rating
Hotel class
Style
More
Style
Hotel brand
More
Hotel brand
  • Sort by:
  • Traveller Ranked
  • Best Value
  • Lowest Price
  • Distance
TripAdvisor members only.
Login for exclusive access to hotel deals up to 40% off
Login to get best prices
The Marker Waterfront Resort
No availability for your dates from these sites
200 William Street, Key West, FL 33040
0.1 km from Key West Sailing Adventure
  • Free Wifi
  • Pool
Cypress House Hotel : Key West
TripAdvisor
US$199
View Deal
601 Caroline St, Key West, FL 33040-6606
0.3 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Savings alert: 11% below average rate

The price you found is 11% lower than this hotel's average rate of US$224/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

The Galleon Resort And Marina
617 Front St, Key West, FL 33040-6620
0.3 km from Key West Sailing Adventure
  • Free Wifi
  • Free Parking
Eden House
Hotels.com
US$185
View Deal
1015 Fleming Street, Key West, FL 33040-6962
0.4 km from Key West Sailing Adventure
  • Free Wifi
  • Free Parking
Savings alert: 16% below average rate

The price you found is 16% lower than this hotel's average rate of US$220/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Simonton Court Historic Inn and Cottages
Agoda.com
US$249
View Deal
320 Simonton St, Key West, FL 33040-6869
0.4 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Hyatt Centric Key West Resort and Spa
TripAdvisor
US$269
View Deal
601 Front Street, Key West, FL 33040-6620
0.4 km from Key West Sailing Adventure
  • Free Wifi
  • Pool
Savings alert: 11% below average rate

The price you found is 11% lower than this hotel's average rate of US$302/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Marquesa Hotel
Travelocity
US$250
View Deal
600 Fleming St, Key West, FL 33040-6826
0.5 km from Key West Sailing Adventure
  • Free Wifi
  • Free Parking
Savings alert: 12% below average rate

The price you found is 12% lower than this hotel's average rate of US$285/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Pier House Resort & Spa
No availability for your dates from these sites
1 Duval St, Key West, FL 33040-6610
0.5 km from Key West Sailing Adventure
  • Free Wifi
  • Pool
Ocean Key Resort & Spa
No availability for your dates from these sites
0 Duval Street, Key West, FL 33040-6611
0.6 km from Key West Sailing Adventure
  • Free Wifi
  • Pool
The Saint Hotel Key West, Autograph Collection
TripAdvisor
US$219
View Deal
417 Eaton St, Key West, FL 33040
0.6 km from Key West Sailing Adventure
  • Free Wifi
  • Pool
Savings alert: 12% below average rate

The price you found is 12% lower than this hotel's average rate of US$249/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Crowne Plaza Key West La Concha
TripAdvisor
US$199
View Deal
430 Duval Street, Key West, FL 33040
0.6 km from Key West Sailing Adventure
  • Free Wifi
  • Pool
Savings alert: 36% below average rate

The price you found is 36% lower than this hotel's average rate of US$264/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Margaritaville Key West Resort & Marina
TripAdvisor
US$269
View Deal
245 Front Street, Key West, FL 33040-8313
0.7 km from Key West Sailing Adventure
  • Free Wifi
  • Pool
Pegasus International Hotel
Travelocity
US$179
View Deal
501 Southard St, Key West, FL 33040-6835
0.7 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Savings alert: 22% below average rate

The price you found is 22% lower than this hotel's average rate of US$229/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Orbitz.com
US$289
View Deal
526 Angela St, Key West, FL 33040-7433
0.8 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Savings alert: 12% below average rate

The price you found is 12% lower than this hotel's average rate of US$328/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Hyatt Sunset Harbor Resort
No availability for your dates from these sites
200 Sunset Way, Key West, FL 33040-8312
0.8 km from Key West Sailing Adventure
  • Free Wifi
  • Pool
Silver Palms Inn
TripAdvisor
US$144
View Deal
830 Truman Avenue, Key West, FL 33040-6426
1.0 km from Key West Sailing Adventure
  • Free Wifi
  • Free Parking
Savings alert: 28% below average rate

The price you found is 28% lower than this hotel's average rate of US$201/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Key Lime Inn Key West
TripAdvisor
US$164
View Deal
725 Truman Ave, Key West, FL 33040-6423
1.0 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Savings alert: 22% below average rate

The price you found is 22% lower than this hotel's average rate of US$211/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Chelsea House Hotel in Key West
Hotels.com
US$160
View Deal
709 Truman Ave, Key West, FL 33040-6423
1.0 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Savings alert: 18% below average rate

The price you found is 18% lower than this hotel's average rate of US$194/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Almond Tree Inn
TripAdvisor
US$287
View Deal
512 Truman Avenue, Key West, FL 33040-3141
1.1 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Savings alert: 13% below average rate

The price you found is 13% lower than this hotel's average rate of US$331/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Lighthouse Court Hotel in Key West
Travelocity
US$169
View Deal
902 Whitehead St, Key West, FL 33040-7423
1.1 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Savings alert: 14% below average rate

The price you found is 14% lower than this hotel's average rate of US$196/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Hotels.com
US$283
View Deal
1004 Duval Street, Key West, FL 33040-3126
1.2 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Savings alert: 16% below average rate

The price you found is 16% lower than this hotel's average rate of US$338/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Sunset Key Cottages
Expedia.com
US$650
View Deal
245 Front Street, Key West, FL 33040
1.2 km from Key West Sailing Adventure
  • Free Wifi
  • Pool
La Te Da Hotel
No availability for your dates from these sites
1125 Duval St, Key West, FL 33040-3156
1.3 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
H2O Suites Hotel
TripAdvisor
US$339
View Deal
1212 Simonton St, Key West, FL 33040
1.4 km from Key West Sailing Adventure
  • Free Wifi
  • Free Parking
Southernmost Beach Resort
No availability for your dates from these sites
1319 Duval Street, Key West, FL 33040
1.5 km from Key West Sailing Adventure
  • Free Wifi
  • Breakfast included
Best Western Hibiscus Motel
No availability for your dates from these sites
1313 Simonton St, Key West, FL 33040-3113
1.5 km from Key West Sailing Adventure
  • Free Wifi
  • Free Parking