Raccoon Key Vacation Packages for 2026
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Raccoon Key Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Kona Kai Oasis
Old Town Key West
$1,527
per person
Nov 23 - Nov 30
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
Kona Kai Oasis is such a great find in Key West! The leadership team was incredibly helpful and accommodating and the room was perfect. You really can’t beat the location either. Walking distance to the beach and downtown. It’s just also a quiet, smaller, beautiful property as opposed to a bigger hotel. Thank you and highly recommend!
Reviewed on Oct 5, 2026
The Key West Hotel
Key West Historic District
$2,849
per person
Nov 23 - Nov 30
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
Property was everything as described, clean, in the heart of the excitement that is Key West
Pool was refreshing and close to tiki bar and local entertainment.
The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w
May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine
Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity
Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator
We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer
Reviewed on Oct 6, 2026
The Marker Key West Harbor Resort
Key West Historic District
$1,942
per person
Nov 23 - Nov 30
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Very nice room with lots of space. Comfortable bed. Nice pool area with an outdoor bar and live music/entertainment. Good food. Friendly, helpful staff. Great location next to the historic seaport and 3 blocks from Duval Street. Lots of shops, restaurants, and bars within easy walking distance. Would definitely stay here again.
Reviewed on Oct 6, 2026
Orchid Key Inn - Adults Only
Old Town Key West
$2,066
per person
Nov 23 - Nov 30
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Ridley House - Key West Historic Inns
Key West Historic District
$1,930
per person
Nov 23 - Nov 30
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Clean rooms and the staff was great
Reviewed on Oct 5, 2026
Amsterdam's Curry Mansion Inn
Key West Historic District
$1,773
per person
Nov 23 - Nov 30
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Book a stay at this historic guesthouse in Key West. Enjoy free WiFi, beach cabanas (surcharge), and a business center. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Great location & easy check-in! We enjoyed our room and the beautiful inn! Improvements would be: communication - we did not see a single person who works there the entire stay and no response to inquiries. For example, we had a great jacuzzi tub but could not use it as there was no plug, Door to balcony was blocked and could not open. Laundry was always full of inn towels and sheets. Side doors were left open, so security was limited. Despite these things, we most likely would stay again!
Reviewed on Oct 6, 2026
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Trying to figure out a way to bundle your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Raccoon Key perfect. In just a few clicks, you can select the best vacation package for you. We have an amazing list of accommodations and flight, and local endeavors to select from.
Raccoon Key Hotels
With 3093 hotels and resorts in Raccoon Key to choose from, you will find one that is perfect for you.
We have fantastic rates on everything from all-inclusive resorts that satisfy all the vacation must-haves to inexpensive hotels perfect for those on looking to save. You can browse our vast catalog of options and choose the accommodation that is best for you and your family. With AARP Travel Center's Raccoon Key hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Raccoon Key
People from all over make this city their vacation destination, and with good reason. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Save with a Raccoon Key Vacation Package
As an AARP Member, you get to take advantage of all the great savings. You can save on select hotels worldwide, flights, and even car rentals. No matter what Raccoon Key vacation package you select, your membership savings helps you get a great deal. So what are you waiting for? Book today and get ready for your Raccoon Key vacation.
Top Hotel Deals
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and Southernmost ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Book a stay at this spa hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...
The Southernmost Inn - Adults Only
525 United Street Key West FL
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3852 North Roosevelt Boulevard Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the pool ...
Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
Winslow's Bungalows - Key West Historic Inns
725 Truman Avenue Key West FL
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
Pier House Resort & Spa
1 Duval St Key West FL
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Mar 1 - Sat, Mar 6
TPA
Tampa Intl.
EYW
Key West Intl.
$137
Roundtrip
found 3 days ago
Sat, Nov 7 - Thu, Nov 12
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$349
Roundtrip
found 23 hours ago
Sat, Nov 7 - Thu, Nov 12
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$349
Roundtrip
found 23 hours ago
Sat, Nov 7 - Thu, Nov 12
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$352
Roundtrip
found 16 hours ago
Sun, Oct 25 - Fri, Nov 6
BOS
Logan Intl.
EYW
Key West Intl.
$367
Roundtrip
found 1 hour ago
Best neighborhoods in Key West
Best points of interest in Key West
- Duval Street Vacations
- Southernmost Point Vacations
- Mallory Square Vacations
- Smathers Beach Vacations
- Ernest Hemingway Home and Museum Vacations
- Fort Zachary Taylor Historic State Park Vacations
- South Beach Vacations
- Clarence S. Higgs Memorial Beach Park Vacations
- Key West Butterfly and Nature Conservatory Vacations
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