Find and compare 2 Star hotels in Sugarloaf Key

Name: Simonton Court Historic Inn & Cottages
Price range: $156 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

$157 nightly

$177 total

Dec 2 - Dec 3

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! (2,014 reviews)

El cuarto estaba limipio y acogedor. El hotel está en un lindo lugar. El desayuno aceptable. Una linda atencion.100% recomendado

Reviewed on Nov 23, 2025

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$221 nightly

$248 total

Dec 9 - Dec 10

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! (1,273 reviews)

Handy location with a very nice shuttle service. Clean and quiet. Highly recommended.

Reviewed on Nov 24, 2025

Southwinds Motel

1321 Simonton Street Key West FL

$167 nightly

$188 total

Dec 2 - Dec 3

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 ...

8.8/10 Excellent! (1,235 reviews)

Nice breakfast and room was nice. Only problem was parking was tight on the side of the hotel we was on. Hotel was in a very nice area and the staff was very good.

Reviewed on Nov 25, 2025

Parmer's Resort

565 Barry Avenue Summerland Key FL

Fully refundableReserve now, pay when you stay

$137 nightly

$154 total

Dec 2 - Dec 3

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 ...

9/10 Wonderful! (1,007 reviews)

We had a wonderful stay at Parmer's Resort. It was quiet and comfortable. We especially loved all the outdoor areas to sit and enjoy the views.

Reviewed on Nov 23, 2025

Pegasus International Hotel

501 Southard Street Key West FL

$160 nightly

$181 total

Dec 3 - Dec 4

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! (1,006 reviews)

Excellent

Reviewed on Nov 28, 2025

Sugar Loaf Lodge

17001 Overseas Hwy Summerland Key FL

Fully refundableReserve now, pay when you stay

$99 nightly

$111 total

Dec 2 - Dec 3

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)

nice water front in the backyard

Reviewed on Nov 26, 2025

Weatherstation Inn

57 Front St Key West FL

Fully refundableReserve now, pay when you stay

$204 nightly

$230 total

Dec 3 - Dec 4

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! (986 reviews)

Very nice Inn, very walkable.

Reviewed on Nov 28, 2025

Old Wooden Bridge Resort and Marina

1791 Bogie Drive Big Pine Key FL

$274 nightly

$308 total

Dec 5 - Dec 6

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 ...

8.6/10 Excellent! (273 reviews)

Good

Reviewed on Nov 23, 2025

Looe Key Reef Resort

27340 Overseas Highway Summerland Key FL

Fully refundableReserve now, pay when you stay

$140 nightly

$158 total

Jan 1 - Jan 2, 2026

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! (1,003 reviews)

Room was really clean and receptionist very friendly. Travelling with my son so had a nice big bed each. Balcony was nice and its only 35 mins to Key West which was oerfect

Reviewed on Nov 9, 2025

Simonton Court Historic Inn & Cottages

320 Simonton St Key West FL

$139 nightly

$156 total

Dec 2 - Dec 3

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! (872 reviews)

Room was super clean, as always. Staff is always amazing. Very cool place. Old Key West style. Great location, close to everything Old Town. I only stay here everytime I come to Key West

Reviewed on Nov 20, 2025

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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.

Recent Sugarloaf Key hotel reviews by fellow wanderers

Southernmost Beach Resort and Guesthouses

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"Our trip was fantastic, the resort is right on the ocean and has a nice beachfront. It's not the largest beach area but was kept nice and had plenty of lounge chairs. Shores pool was to the left of the beach with nice bar and food service. Restaurant was just to the right of the beach with great food choices. The property is pretty large - be sure to view a map before picking your room as you can be right on the beach or in motel style rooms on the street. We stayed in the Dewey house - a bed and breakfast style house which was very nice. I would choose Mer house if we went back as we stayed on first level in Dewey garden view and our room was literally in the kitchen where they prepare breakfast everyday and you could hear clanging dishes at 6am. Also bring ear plugs as the roosters start crowing at 4am. Didn't bother us with the earplugs. The daily breakfast was very nice (paid more for this) with made to order eggs, potatoes, sausage, bacon, waffles, pancakes, etc. I would highly recommend getting the breakfast included."

A verified traveler stayed at Southernmost Beach Resort and Guesthouses