Deals on vacations and trips to Lower Sugarloaf Key

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Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $741, price is now $342 per person
$342
per person
Jan 26 - Jan 29
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.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,434, price is now $561 per person
$561
per person
Jan 22 - Jan 27
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.
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,816, price is now $785 per person
$785
per person
Jan 24 - Jan 31
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.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $11,363, price is now $5,234 per person
$5,234
per person
Mar 3 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This condo resort 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.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was $1,569, price is now $731 per person
$731
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like full breakfast and WiFi in public areas. Valet parking, a terrace, and luggage storage are also offered.

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
$314 nightly
The price is $354 total per night
$354 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.
On private beach
Pool
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
$292 nightly
The price is $329 total per night
$329 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.
Pool
Hot Tub
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$345 nightly
The price is $389 total per night
$389 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.
Pool
Spa
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$307 nightly
The price is $345 total per night
$345 total
Jan 11 - Jan 12, 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.
Pool
Pet friendly
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St Key West FL
Free Cancellation
Reserve now, pay when you stay
$460 nightly
The price is $517 total per night
$517 total
Dec 23 - Dec 24
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.
Pool
Spa
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.
Pool
Free airport shuttle
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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 $342. 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 showing a bay or harbor, a house and a sunset
Sugarloaf Shores which includes a bay or harbor and a house

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