Book Hotels in Rockland Key, FL
Cabins, apartments, houseboats! We offer comfortable & private vacation rentals
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check prices for these dates
Top Rockland Key hotels
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $246 total per night from Nov 1 to Nov 2
$246 total
Nov 1 - Nov 2
Total with taxes and fees
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 hot tub ...
"pool was the best with food and bar right next. shuttle service to town was excellent can't wait to go back!"
Reviewed on Oct 15, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$265 nightly
The price is $298 total per night from Oct 18 to Oct 19
$298 total
Oct 18 - Oct 19
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, ...
"The smell from the seaweed was disgusting !!!"
Reviewed on Oct 14, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $253 total per night from Oct 25 to Oct 26
$253 total
Oct 25 - Oct 26
Total with taxes and fees
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, free WiFi ...
"This property is beautiful and in a great location.My husband and I were here for a ling weekend to celebrate his 60th birthday and had a wonderful time. It was awesome to wake up to the sound of ocean waves and tropical breezes. Oh and I can't forget the roosters.. We weren't sure if we needed a ..."
Reviewed on Oct 15, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$276 nightly
The price is $310 total per night from Oct 25 to Oct 26
$310 total
Oct 25 - Oct 26
Total with taxes and fees
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 ...
"Beautiful Main Hotel, but a Disappointing Stay for the Price Casa Marina has a beautiful main hotel with historic charm, colorful walls, elegant carpeting, and thoughtful details, but our experience in the room area /space was a stark contrast. The surroundings felt cold and concrete - like a cheap ..."
Reviewed on Oct 14, 2026
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $168 total per night from Oct 29 to Oct 30
$168 total
Oct 29 - Oct 30
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
"Beautiful resort. Very good restaurant on site. Shuttle bus to and from Old Town Key West every hour. The staff was exceptional. Highly recommend this resort."
Reviewed on Oct 13, 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $147 total per night from Oct 28 to Oct 29
$147 total
Oct 28 - Oct 29
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public ...
"Beautiful property, clean room. Staff was professional, friendly and courteous."
Reviewed on Oct 15, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $197 total per night from Oct 25 to Oct 26
$197 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a playground, and families will appreciate ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $227 total per night from Oct 27 to Oct 28
$227 total
Oct 27 - Oct 28
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$220 nightly
The price is $248 total per night from Oct 18 to Oct 19
$248 total
Oct 18 - Oct 19
Total with taxes and fees
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 ...
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.
Hotels in Rockland Key with star-rating
Check Rockland Key Hotels by Star Rating
4 Star Hotels
30 properties
Recent Rockland Key hotel reviews by fellow wanderers
Havana Cabana at Key West
5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"pool was the best with food and bar right next. shuttle service to town was excellent can't wait to go back!"
A verified traveler stayed at Havana Cabana at Key West
Explore More Ways to Travel with Travelocity
- Duval House
- Family Friendly in Key West
- H2O Suites - Adults Only
- The Marquesa Hotel
- Winslow's Bungalows - Key West Historic Inns
- Lighthouse Hotel - Key West Historic Inns
- Ella's Cottages - Key West Historic Inns
- Beachside Resort & Residences
- Island City House Hotel
- Suites in Key West
- The Independent Inn - Formerly Heron House Court
- Heron House - Adult Only
- Havana Cabana at Key West
- Wicker Guesthouse
- Hotels in Key West
- Hotels near Key West FL
- Privatevacationhomes in Key West
- Resorts in Key West
- Parmer's Resort
- Hotels in Cow Key
- Casa Marina Hotels
- The Cabana Inn Key West - Adults Only
- Southwinds Motel
- Southernmost Beach Resort and Guesthouses
- Simonton Court Historic Inn & Cottages
- Silver Palms Inn & Historic Homes
- Seashell Motel
- Pier House Resort & Spa
- Parrot Key Hotel & Villas
- Orchid Key Inn - Adults Only
- Opal Key Resort & Marina Key West
- Hilton Key West Resort & Marina
- Truman Annex Hotels
- Sunset Key Hotels
- Sugarloaf Key Hotel at KOA Resort
- Sugar Loaf Lodge
- Hotels near Southernmost Point
- Hotels near South Beach
- Hotels near Smathers Beach
- Old Town Key West Hotels
- Hotels in Marathon
- Tranquility Bay Beachfront Hotel and Resort
- Hotels in Big Pine Key
- Big Coppitt Key Hotels
- LA TE DA Hotel - Adults Only
- Isla Bella Beach Resort & Spa
- Hawks Cay Resort
- Hotels near Mallory Square
- New Orleans House - Gay Men Adult Resort
- NYAH Key West - Adults Only
- Ocean Key Resort - A Noble House Resort
- The Southernmost Inn - Adults Only
- Southernmost House - Adult Exclusive
- The Perry Hotel & Marina Key West
- The Marker Key West Harbor Resort
- The Laureate Key West
- The Gardens Hotel
- Downtown Key West Hotels
- Hotels near Duval Street
- Hotels near Ernest Hemingway Home and Museum
- Hotels near Fort Zachary Taylor Historic State Park
- Hotels near Harry S Truman Little White House
- Historic Seaport Hotels
- Bedandbreakfast in Key West
- Condos in Key West
- Key West Historic District Hotels
- Adults Only in Key West
- All-Inclusive in Key West
- Amsterdam's Curry Mansion Inn
- Beach in Key West
- Casa Marina Key West Curio Collection by Hilton
- Budget in Key West
- Coconut Beach Resort
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Milwaukee (MKE) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Newark (EWR) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from St Louis (STL) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- JetBlue Airways Jamaica (JFK) to Key West (EYW) flights
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights to Key West
- Flights from Alcoa (TYS) to Key West (EYW)
- Hotels in Boca Chica Key
- Hotels in Big Coppitt Key
- Hotels near Duval Street
- All-inclusive Resorts in Key West
- Key West vacations
- Hotels in Stock Island
- Hotels in Cow Key
- Flights to Key West
- Things to do in Stock Island
- Hotels in Geiger Key
- Hotels in Key West
- Hotels in Key Haven
- Hotels near Key West Golf Club
