Find and compare 2 Star hotels in Sugarloaf Key

Name: Simonton Court Historic Inn & Cottages
Price range: $528 total
Rating: 9.6

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Top Sugarloaf Key 2 Star hotels

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$287 nightly

$323 total

Jan 22 - Jan 23

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 ...

8/10 Very Good! (2,056 reviews)

Location was good

Reviewed on Jan 19, 2026

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$422 nightly

$475 total

Jan 27 - Jan 28

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 24-hour ...

9/10 Wonderful! (1,304 reviews)

The room was spotless, the staff was so friendly! The breakfast was included & switched up everyday. They even had an included shuttle to get you downtown & both drivers we interacted with were amazing!

Reviewed on Jan 18, 2026

Southwinds Motel

1321 Simonton Street Key West FL

$349 nightly

$393 total

Jan 26 - Jan 27

Total with taxes and fees

This hotel features 2 outdoor pools and a bar/lounge. Enjoy the free continental breakfast each morning. Self parking, a picnic area, and luggage storage are ...

8.6/10 Excellent! (1,271 reviews)

Everyone was nice and courteous. Quiet place. Really enjoyed our weekend

Reviewed on Jan 20, 2026

Parmer's Resort

565 Barry Avenue Summerland Key FL

Fully refundableReserve now, pay when you stay

$293 nightly

$330 total

Jan 22 - Jan 23

Total with taxes and fees

The private beach and marina are among the highlights at this motel. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Enjoy ...

8.8/10 Excellent! (1,002 reviews)

It’s a special place in paradise for the people who know about it. Rustic and cozy with all the amenities.

Reviewed on Jan 16, 2026

Pegasus International Hotel

501 Southard Street Key West FL

$324 nightly

$365 total

Jan 26 - Jan 27

Total with taxes and fees

This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public ...

8/10 Very Good! (1,023 reviews)

Great location room was neat and clean.

Reviewed on Jan 15, 2026

Sugar Loaf Lodge

17001 Overseas Hwy Summerland Key FL

Fully refundableReserve now, pay when you stay

$199 nightly

$224 total

Jan 22 - Jan 23

Total with taxes and fees

This hotel features a marina, 2 outdoor tennis courts, and a restaurant. Enjoy the outdoor pool and perks like free self parking and free WiFi. A bar/lounge ...

8/10 Very Good! (1,003 reviews)

Great staff and great location!

Reviewed on Jan 7, 2026

Weatherstation Inn

57 Front St Key West FL

$459 nightly

$516 total

Feb 1 - Feb 2

Total with taxes and fees

An outdoor pool, free self parking, and concierge services are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...

9.2/10 Wonderful! (999 reviews)

Awesome location, comfortable, clean room. Very helpful and nice staff

Reviewed on Jan 13, 2026

Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL

$241 nightly

$271 total

Jan 29 - Jan 30

Total with taxes and fees

A marina and an outdoor pool are featured at this cottage. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a picnic ...

8.4/10 Very Good! (289 reviews)

We stayed in a ground cottage ( yellow ) it was what i expected. No frills but clean. The pool was nice but cold ( January) the beds were comfy and the air works well. The hot water is tricky and we only had tv for one out of 5 days. Told the staff at least 3 times with no success. The wifi is very ...

Reviewed on Jan 16, 2026

Looe Key Reef Resort

27340 Overseas Highway Summerland Key FL

Fully refundableReserve now, pay when you stay

$140 nightly

$158 total

Jan 29 - Jan 30

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic ...

7.4/10 Good! (1,001 reviews)

Clean and staffs were good. Little more amenities (kettle, desk and chair would have given a 5 star stay.

Reviewed on Jan 14, 2026

Simonton Court Historic Inn & Cottages

320 Simonton St Key West FL

$469 nightly

$528 total

Jan 25 - Jan 26

Total with taxes and fees

This hotel features free WiFi in public areas, laundry facilities, and self parking. Enjoy the 4 outdoor pools and free continental breakfast each morning. A ...

9.6/10 Exceptional! (897 reviews)

Very friendly, accommodating staff. Convenient location right off Duvall St. Clean, comfortable, well-maintained rooms. Beautiful courtyards and pools. Amazing landscaping and outdoor lighting. Breakfast is waffles, toast, eggs, fruit, yogurt, etc in the courtyard. Very good waffles! We will return ...

Reviewed on Jan 11, 2026

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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.

2 Star Hotels Sugarloaf Key

Looking to break out of your routine for some much needed rest and relaxation? Or maybe you’ve already decided it’s time for a trip and are trying to find affordable hotels in Sugarloaf Key that won’t bust your travel budget?

Sugarloaf Key 2 star hotels will give you everything you need to enjoy the city like a local, saving a ton of money so you can hit all the hot spots in town.

Have a delicious breakfast at your hotel to fuel up for your day of sightseeing, then enjoy amenities like fresh towels and linens, as well as a nice hot shower to unwind after a busy day of experiencing everything the city has to offer.

As you explore a new locale, or one you love to visit over and over, you can rest easy knowing you’re staying in a great hotel that lets you discover Sugarloaf Key and welcomes you back to a clean, comfortable room at night.

Browse Travelocity’s wide selection of 2 star hotels in Sugarloaf Key and find one that’s perfectly priced and places you next to all the best activities and sights. The town is your oyster, and we can help you seek out its secrets while sticking to your budget.