Hotels Near
Sugarloaf Shores

Check Last Minute Sugarloaf Shores Hotel Deals

Tonight Dec 7 - Dec 8Next weekend Dec 12 - Dec 14

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


Featured Sugarloaf Shores Hotels

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
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! (1,742 reviews)
Great service and friendly staff. Great pool

Reviewed on Dec 5, 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
Fully refundableReserve now, pay when you stay
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 ...
8/10 Very Good! (1,750 reviews)
Love this place rooms are wonderful pool view is great. Employees all speak English and are so nice and helpful. Especially Flora

Reviewed on Dec 5, 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
Fully refundableReserve now, pay when you stay
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! (1,747 reviews)
Very nice clean and big room. Great view over the pools and harbor.

Reviewed on Dec 4, 2025

Oceans Edge Key West Resort, Hotel & Marina
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
Fully refundableReserve now, pay when you stay
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! (1,140 reviews)
Hotel is great and a shuttle to Old Town. Did not use the pool and Key West always has some construction going on.

Reviewed on Dec 4, 2025

Hilton Garden Inn Key West / The Keys Collection
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
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! (1,782 reviews)
Rooms clean and smelled good Staff was great! Loved the pool

Reviewed on Dec 5, 2025

Margaritaville Beach House Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
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! (2,891 reviews)
The staff was wonderful, the resort was great and within walking distance from all the fun places on Duval Street as well as 2 mins from the beach.

Reviewed on Dec 6, 2025

Southernmost Beach Resort and Guesthouses
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
Fully refundableReserve now, pay when you stay
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! (1,001 reviews)
IT WAS OUR FIRST TIME IN KEY WEST. THE HOTEL SMELLED GOOD AND WAS VERY CLEAN. THE STAFF WAS NICE AND FOOD WAS FRESH

Reviewed on Nov 30, 2025

DoubleTree Resort by Hilton Grand Key - Key West
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
Fully refundableReserve now, pay when you stay
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! (1,167 reviews)
Property was clean and the room we stayed in had direct pool access so a morning swim was easy. Be advised there is some noise from the local airport and navy base but this didn’t bother me.

Reviewed on Dec 5, 2025

The Perry Hotel & Marina Key West
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
Fully refundable
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! (1,005 reviews)
The Hyatt at Windward Pointe is a beautiful property with outstanding views of the water. The pool area and grounds are clean & well taken care of. Our room was very spacious, clean and had everything we needed. We also like the close proximity to airport and Smathers Beach.

Reviewed on Dec 5, 2025

Hyatt Vacation Club at Windward Pointe, Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
8.8/10 Excellent! (1,727 reviews)
Overall very nice

Reviewed on Dec 3, 2025

Havana Cabana at Key West
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,000 reviews)
Only stay on Key West with a beach. Love it at the Reach!

Reviewed on Dec 4, 2025

The Reach Key West, Curio Collection by Hilton
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

4 out of 5
2801 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
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! (1,175 reviews)
Ambiance of the grounds, front and back door, back porch,

Reviewed on Dec 5, 2025

Parrot Key Hotel & Villas
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.

Hotels in Sugarloaf Shores

Summerland Key is a city that has a lot going on, but you have your sights set on Sugarloaf Shores. This part of town is perfect for what you want to be doing, and that is everything that is not on everyone’s radar. For all that Sugarloaf Shores has going on, you’ll still need a place to crash, eventually. But you don’t want any old shack, you need something that fits the trip. We have a slew of Sugarloaf Shores hotels that will do the trick.

A beautiful day in the neighborhood

As much as you like getting out there, it’s also good to know a part of Summerland Key so well you’ll be telling the tourists where to go. Make friends with the concierge or be bold and chat up a local. It’s your trip, so choose your own adventure. And when you get in at night, you’ll have a comfy room and plenty of amenities to help you settle in. Call a friend and spin tales from the Sugarloaf Shores underground. What’s a journey without a good story to go with it?

Beyond the block

We’re not talking about the Sugarloaf Shores city block. We’re talking about looking beyond that block of hotels you always focus on. We give you tons of ways to sort our stash of Sugarloaf Shores cheap hotels. And if you feel like living a little, but not killing your vacation vibes, choose the Hotwire Hot Rate deal. Filter by:

  • Hotwire Hot Rate: Snag some of the best hotels in Sugarloaf Shores at an almost too good to be true rate. After you book, we’ll reveal the name of the hotel. You can get a luxury hotel at a budget price.
  • Price: You have a price in mind, and we have solutions. Hotels start as low as $161
  • Amenities: Rooftop lounge, designer furniture, 24-7 room service, and everything else you look for to live it up large.

Find the Sugarloaf Shores hotel you want, book it, and never look back. Because your great escape is ahead of you.