Deals on vacations and trips to Lower Sugarloaf Key

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Lower Sugarloaf Key flight + hotel vacation packages

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

Creekside Inn

2.5 out of 5
Price was $1,453, price is now $557 per person
$557
per person
Jan 30 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $2,318, price is now $1,019 per person
$1,019
per person
Feb 1 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
Price was $2,737, price is now $1,216 per person
$1,216
per person
Feb 8 - Feb 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This apartment features an outdoor pool and a 24-hour gym. WiFi in public areas is free. Valet parking and a safe deposit box are also offered on site.
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,684, price is now $760 per person
$760
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Ocean Four
Price was $1,853, price is now $851 per person
$851
per person
Jan 26 - Feb 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. Enjoy the 24-hour gym and unwind at the beach bar and poolside bar.

Top Lower Sugarloaf Key hotels deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$297 nightly
The price is $334 total per night
$334 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$283 nightly
The price is $318 total per night
$318 total
Jan 8 - Jan 9, 2026
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 an arcade/game room, 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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
$292 nightly
The price is $328 total per night
$328 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
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.
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$269 nightly
The price is $303 total per night
$303 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
$360 nightly
The price is $405 total per night
$405 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$333 nightly
The price is $375 total per night
$375 total
Jan 4 - Jan 5, 2026
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.
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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 $557. 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.

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Sugarloaf Shores which includes a bay or harbor and a house

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