Search for Cheap Deals on
Hotels in Sugarloaf Key

Check Last Minute Sugarloaf Key Hotel Deals

Tonight Nov 29 - Nov 30Next weekend Dec 5 - Dec 7

Choose from 3523 Sugarloaf Key Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
  • 29 min drive from Florida Keys Beaches
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,702 reviews)
Staff was so nice to us. Thoroughly enjoyed the experience.

Reviewed on Nov 22, 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
  • 30 min drive from Florida Keys Beaches
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
7.8/10 Good! (1,718 reviews)
The staff was amazing. They greeted us with smiles and welcomed us very nicely. Clean and very comfortable

Reviewed on Nov 22, 2025

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
  • 26 min drive from Florida Keys Beaches
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
8.8/10 Excellent! (1,745 reviews)
Everything was great!

Reviewed on Nov 20, 2025

Oceans Edge Key West Resort, Hotel & Marina
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
  • 36 min drive from Florida Keys Beaches
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (2,879 reviews)
We had a nice view of the beach. The property has very nice pools and they entertain often.

Reviewed on Nov 24, 2025

Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
  • 33 min drive from Florida Keys Beaches
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
8.6/10 Excellent! (1,789 reviews)
Property was very clean and maintained. The restaurant and bars offered great drinks and food, room service was also very nice to have. Access to the nicest beach on key west was perfect. Far enough out of town yet close enough to get into the nightlife. Would definitely stay again.

Reviewed on Nov 19, 2025

Margaritaville Beach House Key West
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
  • 28 min drive from Florida Keys Beaches
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
9.4/10 Exceptional! (1,156 reviews)
Beautiful boutique hotel. Love the art, food, and location. Wish we had stayed here the entire trip.

Reviewed on Nov 21, 2025

The Perry Hotel & Marina Key West
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
  • 29 min drive from Florida Keys Beaches
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
7.8/10 Good! (1,132 reviews)
Great pool and exercise/weight room area!

Reviewed on Nov 23, 2025

Hilton Garden Inn Key West / The Keys Collection
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
  • 29 min drive from Florida Keys Beaches
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8/10 Very Good! (1,017 reviews)
Everyone was very friendly and helpful.

Reviewed on Nov 23, 2025

DoubleTree Resort by Hilton Grand Key - Key West
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
2801 N Roosevelt Blvd Key West FL
  • 32 min drive from Florida Keys Beaches
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,165 reviews)
The room was spacious and clean, my husband and I loved the balcony looking toward the marina 😍 perfect spot to seat down and have our morning coffee, the staff was responsive, efficient and kind! Great location, quiet but a short drive from the main places of interest.

Reviewed on Nov 23, 2025

Parrot Key Hotel & Villas
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
  • 30 min drive from Florida Keys Beaches
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,016 reviews)
Friendly staff and clean

Reviewed on Nov 22, 2025

Hyatt Vacation Club at Windward Pointe, Key West
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue Key West FL
  • 36 min drive from Florida Keys Beaches
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
9.2/10 Wonderful! (1,052 reviews)
Room was extremely clean and spacious

Reviewed on Nov 25, 2025

Winslow's Bungalows - Key West Historic Inns
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
  • 35 min drive from Florida Keys Beaches
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and Southernmost ...
8.2/10 Very Good! (443 reviews)
The hotel is in good state, clean and fresh; the rooms offer plenty of comfort and beach front balcony is a pleasing extra!

Reviewed on Nov 23, 2025

Casa Marina Key West, Curio Collection by Hilton
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.

Find cheap hotels in Sugarloaf Key

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Sugarloaf Key hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Sugarloaf Key.

Choosing the right hotel in Florida has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Sugarloaf Key’s 3,523 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $161. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Sugarloaf Key hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Sugarloaf Key. No matter your reason for visiting Sugarloaf Key, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Sugarloaf Key hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Sugarloaf Key for as low as $161.

How many hotels are there in Sugarloaf Key?

With over 3,523 hotels in Sugarloaf Key, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $161.

How to find cheap car rentals in Sugarloaf Key?

Finding a cheap car rental deal in Sugarloaf Key is as easy as scoring cheap hotels in Sugarloaf Key. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.