
Exclusive Robbie's Vacation Deals

Robbie's vacation package deals
Price found within the past 48 hours. Click for updated prices.

Fitch Lodge - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,617, price is now $1,059 per person
$1,059
per person
May 28 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Concierge services are provided for your convenience.

The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,997, price is now $1,752 per person
$1,752
per person
May 28 - Jun 3
found 1 day ago
Roundtrip non-stop 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 Sunset Harbor, Key West
Old Town Key West
Save 100% on your flight
Price was $2,056, price is now $1,346 per person
$1,346
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free.

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,854, price is now $1,227 per person
$1,227
per person
May 27 - May 31
found 1 day ago
Roundtrip non-stop 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.

The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,874, price is now $1,277 per person
$1,277
per person
May 28 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
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.

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,011, price is now $1,384 per person
$1,384
per person
May 28 - Jun 3
found 1 day ago
Roundtrip non-stop 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.
Frequently asked questions
Top Robbie's hotel deals

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$308 nightly
The price is $347 total per night
$347 total
Apr 26 - Apr 27
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 picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.
Pool
Hot Tub

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$330 nightly
The price is $371 total per night
$371 total
Apr 26 - Apr 27
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

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$314 nightly
The price is $353 total per night
$353 total
Mar 29 - Mar 30
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
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.
Explore More Ways to Travel with Travelocity
- Condos in Cow Key
- Cottages in Cow Key
- Extended Stay Hotels in Cow Key
- Hostels in Cow Key
- Cow Key Hotels
- Houseboats in Cow Key
- Rv Parks in Cow Key
- Resorts in Cow Key
- Apartments in Stock Island
- Condos in Stock Island
- Pet Friendly Hotels in Stock Island
- Stock Island Hotels
- Houseboats in Stock Island
- Vacation Homes in Stock Island
- Resorts in Stock Island
- All Inclusive Resorts & in Key West
- Beach Resorts & in Key West
- Key West Hotels
- Flights from Key West Intl.
- American Airlines Miami (MIA) to Key West (EYW) flights
- Delta Atlanta (ATL) to Key West (EYW) flights
- Jetblue Airways Charleston (CHS) to Key West (EYW) flights
- Jetblue Airways New York (JFK) to Key West (EYW) flights
- Jetblue Airways Boston (BOS) to Key West (EYW) flights
- Jetblue Airways Sarasota (SRQ) to Key West (EYW) flights
- Silver Airways Tampa (TPA) to Key West (EYW) flights
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Austin (AUS) to Key West (EYW)
- Flights from Hartford (BDL) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Cleveland (CLE) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Columbus (CMH) to Key West (EYW)
- Flights from Cincinnati (CVG) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Denver (DEN) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Newark Liberty Intl. Airport (EWR) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Grand Rapids (GRR) to Key West (EYW)
- Flights from Washington (IAD) to Key West (EYW)
- Flights from Houston (IAH) to Key West (EYW)
- Flights from Indianapolis (IND) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from Kansas City (MCI) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Milwaukee (MKE) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Norfolk (ORF) to Key West (EYW)
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- Flights from Pensacola (PNS) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from St. Louis (STL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Knoxville (TYS) to Key West (EYW)
- Flights to Stock Island
- Flights to Key West
- Tingler Island Vacations
- Key West Golf Club
- Ernest Hemingway Home and Museum
- Sombrero Beach
- Fort Zachary Taylor Historic State Park
- Sugarloaf Key Vacations
- Old Town Key West Vacations
- Little Torch Key Vacations
- Fleming Key Vacations
- Pigeon Key
- Ramrod Key Vacations
- Key West Historic District Vacations
- Raccoon Key Vacations
- Cow Key Vacations
- Summerland Key Vacations
- Smathers Beach
- Stock Island Vacations
- Big Pine Key Vacations
- Clarence S. Higgs Memorial Beach Park
- Audubon House and Tropical Gardens
- Southernmost Point
- Mel Fisher Maritime Museum
- Florida Keys Country Club
- Dredgers Key Vacations
- Duval Street
- Uptown - Upper Duval Vacations
- Key West Vacations
- South Beach
- Donkey Milk House
- Seven Mile Bridge