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Deals on vacations and trips to Stock Island
Save when you book Stock Island package deals
Stock Island flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
![Southernmost Beach Resort](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/8db64b55_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Southernmost Beach Resort
Old Town Key West
Save 100% on your flight
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.
![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/17dd6b9a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Ibis Bay Beach Resort
Northside Resort
Save 100% on your flight
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.
![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/8ab7a790_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
Save 100% on your flight
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.
![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/d5fbdab2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Winslow's Bungalows - Key West Historic Inns
Key West Historic District
Save 100% on your flight
per person
Aug 25 - Sep 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking and luggage storage are also offered on site.
Top Stock Island hotels deals
![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $161 per night
$161
per night
Jun 25 - Jun 26
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. There's a restaurant and a bar/lounge for dining and drinks, and also a gym on site.
Pool
Pet friendly
![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Perry Hotel & Marina Key West
7001 Shrimp Road, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $195 per night
$195
per night
Jun 18 - Jun 19
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.
Pool
Pet friendly
![Margaritaville Beach House Key West](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/638b50bb_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $189 per night
$189
per night
Jun 30 - Jul 1
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.
Pool
Pet friendly
![Southernmost Beach Resort](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/8db64b55_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Southernmost Beach Resort
1319 Duval Street, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $201 per night
$201
per night
Jun 16 - Jun 17
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Pool
Spa
![Havana Cabana at Key West](https://images.trvl-media.com/lodging/22000000/21250000/21241100/21241090/ac052f9a_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Havana Cabana at Key West
3420 N. Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $159 per night
$159
per night
Jun 30 - Jul 1
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the spa tub and perks like free self parking.
Pool
Hot Tub
![Fairfield Inn and Suites by Marriott Key West](https://images.trvl-media.com/lodging/1000000/10000/9000/8946/899a2a26_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd, Key West, FL
Free Cancellation
Reserve now, pay when you stay
The price is $149 per night
$149
per night
Jun 18 - Jun 19
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking. A poolside bar, a 24-hour front desk, and a terrace are also provided.
Pool
Breakfast included
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.
Popular places to visit
Duval Street
4.5/5(3,475 reviews)
With a visit to Duval Street, a favorite shopping spot in Key West, you can search for that perfect souvenir. Wander the seaside or discover the area's beautiful sunsets.
Smathers Beach
4/5(1,151 reviews)
Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.
Mallory Square
4.5/5(3,096 reviews)
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
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![Stock Island](https://mediaim.expedia.com/destination/1/25502627a238c74e4ecdd7075f3e48f3.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)
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