Deals on vacations and trips to Lower Florida Keys

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Lower Florida Keys flight + hotel vacation packages

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Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was $1,267, price is now $791 per person
$791
per person
Jan 31 - Feb 3
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 Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Save 100% on your flight
Price was $3,970, price is now $2,248 per person
$2,248
per person
Feb 8 - Feb 14
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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
Price was $2,492, price is now $1,497 per person
$1,497
per person
Feb 8 - Feb 14
found 1 day ago
Roundtrip non-stop 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.
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
Price was $1,609, price is now $979 per person
$979
per person
Feb 28 - Mar 4
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.
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
Price was $2,327, price is now $1,521 per person
$1,521
per person
Feb 28 - Mar 4
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. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Top Lower Florida Keys hotels deals

Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $158 total per night
$158 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-in, and luggage storage are also on offer.
Pool
Pet friendly
Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$243 nightly
The price is $273 total per night
$273 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
The private beach and marina are among the highlights at this motel. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Enjoy the outdoor pool and free perks like on-the-go breakfast and free self parking.
On private beach
Pool
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $224 total per night
$224 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a marina, 2 outdoor tennis courts, and a restaurant. Enjoy the outdoor pool and perks like free self parking and free WiFi. A bar/lounge and a garden are also provided.
Pool
Parking included
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
Get rates
The private beach and marina are among the highlights at this hotel. Enjoy the outdoor pool and perks like free self parking and free WiFi. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
On private beach
Pool
Little Torch Cottages

Little Torch Cottages

2 out of 5
28501 Channel View Drive Summerland Key FL
Get rates
This hotel's 2 outdoor pools and sauna are among the featured amenities. Free self parking and laundry facilities are also offered on site.
Pool
Parking included
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key FL
Get rates
An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
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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.

Popular places to visit

Duval Street featuring signage

Duval Street

With a visit to Duval Street, a favorite shopping spot in Key West, you can search for that perfect souvenir. Wander the seaside or discover the area's beautiful sunsets.

Duval Street
South Beach which includes a beach and a coastal town as well as a large group of people

Florida Keys Beaches

Why not spend a lazy afternoon at Florida Keys Beaches during your trip to Long Beach Estates?

Florida Keys Beaches
Mallory Square which includes a sunset and a bay or harbor as well as a large group of people

Mallory Square

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

Mallory Square

Frequently asked questions

How much are vacation packages to Lower Florida Keys?
Your vacation dreams can all come true in Lower Florida Keys for only $791. Package deals include flights and hotels, so they're bound to make booking a breeze. The only thing you'll have to worry about is having a good time.
Where can I get the best vacation package deals for Lower Florida Keys?
You'll come across an amazing range of Lower Florida Keys package deals on Travelocity. With no less than 400 partner airlines and 1,000,000 properties across the globe, putting together the perfect escape won't take long.
Why should I purchase my Lower Florida Keys vacation bundle via Travelocity?
With our Price Match Guarantee, we'll match any better price you find. Add to that our 24/7 customer support and superb service and your perfect vacation is well within reach.
Will I save money on my Lower Florida Keys car rental if I combine it with a hotel or flight?
Certainly. And our Lower Florida Keys vacation packages are the ideal way to do it. In just a few clicks you can save money as well as time by booking everything in one place. Pick up the keys to your rental car then chart your own course. Looking for things to do? Throw some tours or experiences into your package and save on those too.
What is there to do in Lower Florida Keys?
A vibrant and attractive destination, Lower Florida Keys is home to some terrific things to see and do. Boca Chica Nude Beach and Boca Chica Beach are some of the very best.

Photos of local treasures

Browse Lower Florida Keys vacation photos for more inspiration

Lower Florida Keys
Key West featuring a marina, a coastal town and general coastal views
Big Pine Key featuring a river or creek, a bay or harbor and general coastal views
Embassy Row
Smathers Beach showing a bay or harbor, tropical scenes and windsurfing

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