
Deals on vacations and trips to Rockland Key
Save when you book Rockland Key package deals

Rockland Key flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $919, price is now $583 per person
$583
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
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. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

The Key West Hotel
Key West Historic District
Price was $2,096, price is now $1,112 per person
$1,112
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.

Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,649, price is now $946 per person
$946
per person
Jan 26 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit box and concierge services are also provided.

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,142, price is now $677 per person
$677
per person
Jan 19 - Jan 22
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, a garden, and luggage storage are also offered.

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,039, price is now $623 per person
$623
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.
Top Rockland Key hotels deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$193 nightly
The price is $217 total per night
$217 total
Nov 30 - Dec 1
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 at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.
On private beach
Pool

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$157 nightly
The price is $177 total per night
$177 total
Dec 1 - Dec 2
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 an arcade/game room, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$217 nightly
The price is $244 total per night
$244 total
Nov 30 - Dec 1
Total with taxes and fees
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. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.
Pool
Pet friendly

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$233 nightly
The price is $263 total per night
$263 total
Dec 2 - Dec 3
Total with taxes and fees
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

Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
$235 nightly
The price is $264 total per night
$264 total
Dec 2 - Dec 3
Total with taxes and fees
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

Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$322 nightly
The price is $362 total per night
$362 total
Nov 30 - Dec 1
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.
Pool
Spa
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.
Photos of local treasures
Browse Rockland Key vacation photos for more inspiration
Book a vacation to Rockland Key
Explore More Ways to Travel with Travelocity
- All Inclusive Resorts & in Key West
- Beach Resorts & in Key West
- 3 Star Hotels in Key Haven
- 5 Star Hotels in Key Haven
- Condo Resorts in Key Haven
- Cheap Hotels in Key Haven
- Key Haven Hotels
- Condos in Raccoon Key
- Raccoon Key Hotels
- Vacation Homes in Raccoon Key
- Beach Resorts & in Big Coppitt Key
- Hotels with Pools in Big Coppitt Key
- Big Coppitt Key Hotels
- Hotels near Key West Naval Station
- Geiger Key Hotels
- 2 Star Hotels in Boca Chica Key
- Apartments in Boca Chica Key
- Cheap Hotels in Boca Chica Key
- Highgate Independent Hotels in Boca Chica Key
- Pet Friendly Hotels in Boca Chica Key
- Boca Chica Key Hotels
- Motels in Boca Chica Key
- Rv Parks in Boca Chica Key
- Apartments in Stock Island
- Condos in Stock Island
- Hotels with Free Parking in Stock Island
- Pet Friendly Hotels in Stock Island
- Stock Island Hotels
- Houseboats in Stock Island
- Motels in Stock Island
- Vacation Homes in Stock Island
- Resorts in Stock Island
- Hotels near Saddlebunch Keys
- Hotels near Boca Chica Nude Beach
- Flights to Key West
- Flights from San Francisco to Key Haven
- Flights from Tampa to Key Haven
- Flights to Raccoon Key
- Flights from Chicago to Raccoon Key
- Flights from Nashville to Raccoon Key
- Flights from Atlanta to Boca Chica Key
- Flights from Baltimore to Boca Chica Key
- Flights from Boston to Boca Chica Key
- Flights from Cleveland to Boca Chica Key
- Flights from Columbus to Boca Chica Key
- Flights from Indianapolis to Boca Chica Key
- Flights from Minneapolis - St. Paul to Boca Chica Key
- Flights from New York to Boca Chica Key
- Flights from Orlando to Boca Chica Key
- Flights from Philadelphia to Boca Chica Key
- Flights from San Francisco to Boca Chica Key
- Flights from Seattle to Boca Chica Key
- Flights from Washington to Boca Chica Key
- Flights from Pittsburgh to Boca Chica Key
- Jetblue Airways New York (JFK) to Key West (EYW) flights
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights to Stock Island
- Ramrod Key Vacations
- Sombrero Beach
- Tingler Island Vacations
- Uptown - Upper Duval Vacations
- Cow Key Vacations
- Key West Vacations
- Ernest Hemingway Home and Museum
- Summerland Key Vacations
- Robbie's
- Dredgers Key Vacations
- Raccoon Key Vacations
- Donkey Milk House
- Key West Historic District Vacations
- Sugarloaf Key Vacations
- Big Pine Key Vacations
- Seven Mile Bridge
- Old Town Key West Vacations
- Smathers Beach
- Key West Golf Club
- Clarence S. Higgs Memorial Beach Park
- Fort Zachary Taylor Historic State Park
- Little Torch Key Vacations
- Fleming Key Vacations
- Southernmost Point
- Mel Fisher Maritime Museum
- Duval Street
- South Beach
- Pigeon Key
- Stock Island Vacations
- Audubon House and Tropical Gardens
