Lower Keys Vacation Packages 2025/2026 from $331

Lower Keys flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

DoubleTree Resort by Hilton Grand Key - Key West

$331

per person

Oct 27 - Oct 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free beach shuttle.

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$571

per person

Oct 27 - Oct 30

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.

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$470

per person

Oct 27 - Oct 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a poolside bar. 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.

The Perry Hotel & Marina Key West

Save 100% on your flight

$379

per person

Oct 27 - Oct 30

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.

The Reach Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

$626

per person

Oct 27 - Oct 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This resort features a private beach, a full-service spa, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.

Top Lower Keys hotels deals

Parmer's Resort

565 Barry Avenue, Summerland Key, FL

Free Cancellation

Reserve now, pay when you stay

$148 nightly

$167 total

Sep 21 - Sep 22

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

Old Wooden Bridge Resort and Marina

1791 Bogie Drive, Big Pine Key, FL

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A marina and an outdoor pool are featured at this cottage. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a picnic area, and express check-in are also on offer.

Pool

Pet friendly

Sugar Loaf Lodge

17001 Overseas Hwy, Summerland Key, FL

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$111 total

Aug 24 - Aug 25

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

251 Co Rd 939, Summerland Key, FL

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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

Looe Key Reef Resort

27340 Overseas Highway, Summerland Key, FL

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$127 total

Sep 1 - Sep 2

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

Old Florida Style, wrap around porch, boat basin for dockage, open water

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This vacation home includes a garden and laundry facilities.

Kitchen

Washer

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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

Bahia Honda State Park

You can take time to visit Bahia Honda State Park during your travels to Big Pine Key. While you're in the area, wander around the natural setting.

Calusa Beach

Why not spend a lazy afternoon at Calusa Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting.

Boca Chica Beach

Why not spend a lazy afternoon at Boca Chica Beach during your trip to Key West? Stroll along the area's seaside, or simply savor its lively bars.

Frequently asked questions

How much are vacation packages to Lower Keys?

Enjoy a memorable travel experience in Lower Keys with a vacation package starting at $331. Reserving your flights and hotels through Travelocity has never been so easy. What's more, our vacation deals will leave you with more savings for loads of fun times.

Where can I get the best vacation package deals for Lower Keys?

For an affordable Lower Keys package deal, nothing compares to Travelocity. Pick from as many as 400 air carriers and 1,000,000 properties worldwide to create your dream adventure — you're spoiled for choice!

Why should I purchase my Lower Keys vacation bundle via Travelocity?

Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on 24/7 customer support. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.

Will I save money on my Lower Keys car rental if I book it with a hotel or flight?

You can with our Lower Keys vacation packages. With one of these, there are plenty of ways to make your travel budget go further. Bundle any two or more car, flight, hotel and tour bookings and see the savings add up. With a rental car, all the attractions around Lower Keys are within your reach.

What is there to do in Lower Keys?

A diverse and exciting destination, Lower Keys offers some excellent tourist attractions. Boca Chica Nude Beach and Boca Chica Beach are two of the favorites.