Key West Vacations
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Key West Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
$1,122
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Gulfport (GPT) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Kona Kai Oasis
Old Town Key West
$1,278
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Gulfport (GPT) 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 South Beach are located nearby.
This room was disgustingly filthy. The front security did not work, you had to shove the door hard to get it to close. The carpets looked like someone poured oil on them. You could not walk in this room without shoes. Your socks or feet would turn black.
Reviewed on Aug 8, 2026
The Marker Key West Harbor Resort
Key West Historic District
$1,638
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Gulfport (GPT) 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.
Everything was excellent, the only thing was my Brother and I requested an 1 1/2 late checkout, he's handicapped and it would have helped not having to rush but were denied.
Reviewed on Aug 8, 2026
Pier House Resort & Spa
Key West Historic District
$1,605
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Gulfport (GPT) to Key West (EYW)
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 in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Questionable billing practices. Held over 3x the amount of the room, locking up thousands of available credit. Mentioned it to the staff and they continued to charge me. I’ve been coming to Key West for years and have never experienced that. Almost ruined the trip.
Also water pressure is horrible. Will not come back. Definitely not worth the money.
Reviewed on Aug 8, 2026
Southernmost Beach Resort and Guesthouses
Old Town Key West
$1,264
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Gulfport (GPT) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.
Disappointing Stay — Not What We Expected From a “Beach Resort”
Unfortunately, our stay at Southernmost Beach Resort was very disappointing and did not live up to our expectations, particularly considering the price and how the property is marketed.
The rooms were not up to the standard we expected from a resort in this price range. Overall, the property and amenities also felt underwhelming and did not provide the resort experience we anticipated.
Even more disappointing was the service. We did not find the staff particularly friendly or welcoming, which makes a significant difference when you are spending your vacation—and your money—at a resort.
Our biggest frustration, however, was the beach. The beach was essentially unusable because of the amount of seaweed. Obviously, the resort cannot control Mother Nature or the seaweed conditions, and I would never fault them for that. What I do fault them for is the lack of transparency. When a property specifically markets itself as a beach resort, guests should be made aware prior to arrival when the beach is currently in a condition that makes it practically unusable. Had we known, it absolutely would have factored into our decision about where to stay.
We travel often and understand that not every hotel or resort will be perfect, but this stay simply did not meet the level of quality, hospitality, or overall experience we expected. I would strongly encourage future guests to check the current beach conditions
Reviewed on Aug 8, 2026
Duval s Duet on Duval by Brightwild
Old Town Key West
$6,271
per person
Oct 16 - Oct 20
found 21 hours ago
Roundtrip non-stop flight included
Gulfport (GPT) to Key West (EYW)
Stay at this apartment in Key West. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Key West Vacation Packages
Looking for ways save both time and money on your upcoming vacation to Key West? Don't worry, as AARP Travel Center Powered by Expedia® is here to help. We're here to book everything you'll need to make your Key West trip one to remember. In just a few clicks, you can pick the best vacation package for you. We have an incredible choice of accommodations and flight, as well as Key West endeavors to choose from.
Key West Hotel Deals
You can choose from around 2639 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Key West hot spots, we have plenty of options available.
We have great deals on everything from luxury hotels that satisfy all the vacation must-haves to affordable hotels perfect for those on wanting to save a little money. You can scan all the possibilities and pick the accommodation that is ideal for you. With AARP Travel Center's Key West hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Key West
Key West has around 25,755 people that call this city their home. If you wanted to take a break from the hustle and bustle of a big city, then you are in the right spot. There are around 14 great attractions in and around Key West that will make vacation a bit of an adventure. Not sure where to begin? Here are a several things that the area is known for:
- Smathers Beach
- Audubon House & Tropical Gardens
- Harry S. Truman Little White House
- Mallory Square
If you are looking for more, then head over to our "Things to Do" tab for more inspiration or to reserve an activity in Key West.
Book Together and Save
As an AARP Member, you can benefit from all the great savings. You'll save on select hotels worldwide, flights, and car rentals. No matter what Key West vacation package you pick, you can rest easy knowing that you already saved on your trip. So what are you waiting for? Book now and get ready for your Key West vacation.
Top Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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. ...
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 ...
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. ...
Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
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. ...
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), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
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 ...
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 South Beach ...
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 ...
La Concha Key West, Autograph Collection
430 Duval St Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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 ...
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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.
Tue, Sep 8 - Thu, Sep 24
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$259
Roundtrip
found 6 days ago
Mon, Oct 19 - Fri, Oct 23
BOS
Logan Intl.
EYW
Key West Intl.
$277
Roundtrip
found 2 days ago
Mon, Oct 19 - Fri, Oct 23
BOS
Logan Intl.
EYW
Key West Intl.
$342
Roundtrip
found 2 days ago
Tue, Sep 8 - Sat, Sep 26
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$359
Roundtrip
found 6 days ago
Best neighborhoods in Key West
Best points of interest in Key West
- Duval Street Vacations
- Mallory Square Vacations
- Southernmost Point Vacations
- Smathers Beach Vacations
- Dry Tortugas National Park Vacations
- Fort Zachary Taylor Historic State Park Vacations
- Ernest Hemingway Home and Museum Vacations
- South Beach Vacations
- Clarence S. Higgs Memorial Beach Park Vacations
- Florida Keys National Marine Sanctuary Vacations
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All accommodation types in Key West
More Types of Hotels
- Hotels with Air Conditioning in Key West
- Hotels with a Pool in Key West
- Beach Hotels in Key West
- Hotels with WiFi in Key West
- Hotel with wifi in Key West
- Hotels with Balconies in Key West
- Hotels with Bars in Key West
- Family Hotels in Key West
- Hotel with a Concierge in Key West
- Hotels with Hot Tubs in Key West
- Luxury Hotels in Key West
- Hotels with Complimentary Breakfast in Key West
- Resorts & Hotels with Spas in Key West
- Smoke Free Hotels in Key West
- Cheap Hotels in Key West
- Hotels with smoking rooms in Key West
- Pet-friendly Hotels in Key West
- Oceanfront Hotels in Key West
- Adults Only Resorts & Hotels in Key West
- Hotels with Tennis Courts in Key West
- Hotels on the River in Key West
- Lakefront Hotels in Key West
- Hotels with Free Airport Shuttle in Key West
- Hotels with Early Check-in in Key West
- Gay friendly Hotels in Key West
- Scuba Diving in Key West
- Hotels with Fireplaces in Key West
- All-inclusive Hotel in Key West