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The best cottages in Sugarloaf Shores

Check out our selection of great cottages in Sugarloaf Shores

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Sun Outdoors Sugarloaf Key, hotel in Summerland Key

Sun Outdoors Sugarloaf Key provides air-conditioned accommodations in Summerland Key. Both free Wifi and parking on-site are accessible at the vacation home free of charge.

Great location and amenities
Scored 9.3
9.3
Rated wonderful
Wonderful
141 reviews
Price from
$259
1 night, 2 adults
Grand Marina Suite -Waterfront Condo, hotel in Key West

5.7 miles from Ernest Hemingway Home and Museum in Key West, Grand Marina Suite -Waterfront Condo provides accommodations with access to a fitness center.

Great communications with the rental agent / owner. Easy access into the property and into the condo. TONS of space in the condo (both bedrooms and bathrooms are large with more than amble floor space), and had everything we needed. Pool was awesome, the workout facility was adequate for it's size and my husband enjoyed the sauna. We liked the location, it is about a 20 minute drive to Duval Street but it was quiet in our area. We enjoyed sitting on the patio, which overlooked the pool and marina, and watching the boats (yachts!) come into the marina (and watched a storm rolling in one evening). Both bedrooms are considered Master Suites and both had French Door access to a patio; so this setup would work great for two couples traveling together. There are two assigned parking spaces. Plenty of towels, including pool towels plus washer and dryer. Sofa sleeper in living room.
Scored 8.7
8.7
Rated excellent
Excellent
106 reviews
Price from
$332.10
1 night, 2 adults
St Kitts - Downtown Waterfront Penthouse Pool Dock Parking, hotel in Key West

Just 1.1 miles from Ernest Hemingway Home and Museum and 1.1 miles from Duval Street, St Kitts - Downtown Waterfront Penthouse Pool Dock Parking features accommodations in Key West with a garden.

Nice facilities. Beds were comfy, good water flow, clean, quiet, big rooms. Great views from the decks.
Scored 9.1
9.1
Rated wonderful
Wonderful
9 reviews
Price from
$956
1 night, 2 adults
The St Martin -Hot Tub & Pool, hotel in Key West

The St Martin -Hot Tub & Pool offers accommodations in Key West, 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

Scored 9.4
9.4
Rated wonderful
Wonderful
10 reviews
Price from
$261.99
1 night, 2 adults
The Exuma Cay -Pool View & Parking, hotel in Key West

The Exuma Cay -Pool View & Parking offers accommodations in Key West, 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

Very clean. Quiet with exception to roosters in the morning (and that is just a part of KW charm). Nice pool. Easy parking. Little store walking distance for small items like yogurt... Right amount of dishes, pots/pans, flatware. Seats 6 at table comfortably. We had two bedrooms with two full baths and pull out bed in living room, plus a terrace with 4 seats and a table--perfect for our family. Just minutes from the busy KW town by car, but also plenty of biking trails to get downtown or just walk. Great hosts... I could text anything and they were quick to answer. Plenty of towels including pool/beach towels.
Scored 9.3
9.3
Rated wonderful
Wonderful
22 reviews
Price from
$277.98
1 night, 2 adults
The Barbados -Bright Condo w Pool, hotel in Key West

The Barbados -Bright Condo w Pool is located in Key West, just 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

We enjoyed the location, as well as the pool, which is large and beautiful. It’s a secluded spot close to beaches, marinas, and restaurants.
Scored 8.3
8.3
Rated very good
Very Good
56 reviews
Price from
$227.55
1 night, 2 adults
The Trinidad -Pool & Parking, hotel in Key West

The Trinidad -Pool & Parking is located in Key West, just 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

Comfortable and very well stocked with household essentials.
Scored 8.0
8.0
Rated very good
Very Good
28 reviews
Price from
$214.02
1 night, 2 adults
Tortuga Suite at Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking, hotel in Key West

Tortuga Suite at Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking is located in Key West, just 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

Clean and comfortable. Spacious
Scored 8.6
8.6
Rated excellent
Excellent
28 reviews
Price from
$192.37
1 night, 2 adults
The Grand Turk -Sunset View & Pool, hotel in Key West

The Grand Turk -Sunset View & Pool offers accommodations in Key West, 4 miles from Southernmost Point and 4.6 miles from Ernest Hemingway Home and Museum.

The location
Scored 6.5
6.5
Rated pleasant
Pleasant
15 reviews
Price from
$232.47
1 night, 2 adults
Pelican's Roost, Waterfront comfort at Venture Out, hotel in Cudjoe Key

Featuring free bikes, Pelican's Roost, Waterfront comfort at Venture Out provides accommodations in Cudjoe Key.

Location, attention to detail, and soooo many amenities!
Scored 9.2
9.2
Rated wonderful
Wonderful
15 reviews
All cottages in Sugarloaf Shores
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  • Avg. price/night: $336.38
    Scored 7.4
    7.4
    Rated good
    Good
     · 567 reviews
    Old, charming hotel—that was the reason we booked there. The room was clean, the shower was hot, and the view was beautiful. We loved the look and the setting of the place!
    Judith
    Young couple