Lower Sugarloaf Key Vacation Packages 2026 from $444

Lower Sugarloaf Key flight + hotel vacation packages

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

Cavalier Hotel South Beach

South Beach

$444

per person

Jan 21 - Jan 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$20,902

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This aparthotel features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.

501 First Studio Balcony by Palermo Home

Downtown Miami

$803

per person

Jan 16 - Jan 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

An outdoor pool is featured at this apartment, along with valet parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

Avi Lux Stay

East Fort Lauderdale

$629

per person

Dec 16 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

8 hot tubs, an outdoor pool, and a gym are all featured at this smoke-free aparthotel. WiFi in public areas is free. Valet parking, a 24-hour business center, and luggage storage are also offered.

Miami Vacation Rentals Downtown with Pool

Downtown Miami

$1,198

per person

Feb 1 - Feb 6

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A poolside bar, a coffee shop, and a terrace are also provided.

Top Lower Sugarloaf Key hotels deals

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL

$285 nightly

$321 total

Nov 18 - Nov 19

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like a free airport shuttle. You'll appreciate the hot tub, poolside bar, and concierge services.

Pool

Hot Tub

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

$172 nightly

$194 total

Nov 30 - Dec 1

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

$166 nightly

$187 total

Nov 15 - Nov 16

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 a playground, 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

Pet friendly

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Get rates

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

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

$230 nightly

$259 total

Dec 15 - Dec 16

Total with taxes and fees

This Art Deco hotel features a private beach, a marina, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. Enjoy the outdoor pool and free perks like continental breakfast and WiFi in public areas.

On private beach

Pool

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

$286 nightly

$322 total

Nov 23 - Nov 24

Total with taxes and fees

A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free WiFi.

On private beach

Pool

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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.

Frequently asked questions

How much are vacation packages to Lower Sugarloaf Key?

Travelocity offers hotel and flight vacation packages from just $444. With such great bargains, you'll be exploring all of Lower Sugarloaf Key before too long.

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

Landing the perfect package deal to Lower Sugarloaf Key is a piece of cake with Travelocity. With as many as 400 airlines and 1,000,000 properties all over the globe, you're flush with choice when picking your flights and hotels.

Why should I purchase my Lower Sugarloaf Key vacation package with Travelocity?

We offer destinations and experiences for every type of traveler, top-notch service and customer support available 24/7. To top that off, we'll match any lower price you discover with our Price Match Guarantee.

Will I save money on my Lower Sugarloaf Key car rental if I combine it with hotels and flights?

Combining your bookings into a Lower Sugarloaf Key vacation package will save you a handsome sum. Combine a flight and car; a flight, hotel and car; or a hotel and car. You won't find a better way to discover the greater Lower Sugarloaf Key region than from the driver's seat of your own rental car. You can also add experiences and activities to your Travelocity package.