Compare Sugarloaf Key Guest House Rentals

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Featured Guest Houses in Sugarloaf Key

Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3 out of 5
511 Caroline St Key West FL
$335 nightly
The price is $377 total per night
$377 total
Dec 21 - Dec 22
Total with taxes and fees
Guests of Amsterdam's Curry Mansion Inn enjoy an outdoor pool, free WiFi in public areas, and a business center. Transportation is made easy with an area shuttle. A multilingual staff is on hand to assist with concierge services, dry cleaning/laundry, and securing valuables. Other amenities at this boutique guesthouse include coffee/tea in a common area, a library, and express check-out.
Pool
Pet friendly
NYAH Key West - Adults Only

NYAH Key West - Adults Only

3 out of 5
420 Margaret Street Key West FL
$166 nightly
The price is $187 total per night
$187 total
Dec 22 - Dec 23
Total with taxes and fees
3 outdoor pools, a rooftop terrace, and a hot tub are featured at NYAH Key West - Adults Only. The front desk has multilingual staff standing by 24 hours a day to assist with luggage storage and concierge services. Other amenities at this adults-only guesthouse include coffee/tea in a common area, a terrace, and a water dispenser.
Pool
Hot Tub
The Cabana Inn Key West - Adults Only

The Cabana Inn Key West - Adults Only

3 out of 5
413 Applerouth Lane Key West FL
$339 nightly
The price is $381 total per night
$381 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Guests of The Cabana Inn Key West - Adults Only enjoy an outdoor pool, a hot tub, and coffee in a common area. Self parking is offered for USD 32.25 per night. The front desk has multilingual staff that can help with concierge services and luggage storage. Other amenities at this adults-only guesthouse include express check-out, a terrace, and laundry facilities.
Pool
Hot Tub
The Palms Hotel

The Palms Hotel

3 out of 5
820 White St Key West FL
$228 nightly
The price is $256 total per night
$256 total
Dec 23 - Dec 24
Total with taxes and fees
At The Palms Hotel, guests have access to an outdoor pool, free WiFi in public areas, and coffee in a common area. Free offsite parking is available if you drive. The front desk has multilingual staff that can help with tours or tickets, luggage storage, and securing valuables. Additional amenities include a microwave in a common area, a computer station, and barbecue grills.
Pool
Breakfast included
Wicker Guesthouse

Wicker Guesthouse

3.5 out of 5
913 Duval Street Key West FL
$279 nightly
The price is $314 total per night
$314 total
Dec 20 - Dec 21
Total with taxes and fees
Guests of Wicker Guesthouse enjoy features like an outdoor pool, free WiFi in public areas, and an arcade/game room. If you plan to drive, free parking is available. Front-desk staff can assist with luggage storage, concierge services, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a library, free newspapers, and a terrace.
Pool
Breakfast included
Heron House Court - Adult Only

Heron House Court - Adult Only

3 out of 5
412 Frances St Key West FL
$193 nightly
The price is $217 total per night
$217 total
Dec 19 - Dec 20
Total with taxes and fees
At Heron House Court - Adult Only, guests have access to an outdoor pool, a rooftop terrace, and free WiFi in public areas. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Other amenities at this adults-only guesthouse include coffee/tea in a common area, a terrace, and a garden.
Pool
Free WiFi
Douglas House

Douglas House

3 out of 5
419 Amelia St Key West FL
$235 nightly
The price is $264 total per night
$264 total
Dec 23 - Dec 24
Total with taxes and fees
Guests of Douglas House enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. Self parking is available for USD 29.99 per day. Front-desk staff can assist with luggage storage and tours/tickets. Additional amenities include a picnic area and a garden.
Pool
Free WiFi
Bishop Hotel Key West

Bishop Hotel Key West

4 out of 5
822 Fleming St Key West FL
2 outdoor pools, free WiFi in public areas, and a hot tub are featured at Bishop Hotel Key West. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. This adults-only guesthouse also has an ATM.
Pool
Hot Tub
Duval Inn

Duval Inn

3 out of 5
511 Angela Street Key West FL
$241 nightly
The price is $271 total per night
$271 total
Dec 19 - Dec 20
Total with taxes and fees
Guests of Duval Inn enjoy features like an outdoor pool, free WiFi in public areas, and free newspapers. If you decide to drive, there's free offsite parking. Front-desk staff can assist with tours/tickets and luggage storage. Additional amenities include a terrace, a garden, and wedding services.
Pool
Breakfast included
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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.

Hotel Options in Sugarloaf Key

    Beachside Resort & Residences

    Beachside Resort & Residences

    3841 N Roosevelt Blvd Key West FL
    $346 nightly
    The price is $390 total per night from Dec 19 to Dec 20
    $390 total
    Dec 19 - Dec 20
    Total with taxes and fees
    8.6/10 Excellent! (1,780 reviews)
    Blue Flamingo Resort Key West

    Blue Flamingo Resort Key West

    3820 North Roosevelt Boulevard Key West FL
    $265 nightly
    The price is $298 total per night from Dec 21 to Dec 22
    $298 total
    Dec 21 - Dec 22
    Total with taxes and fees
    8/10 Very Good! (1,763 reviews)
    Southernmost Beach Resort and Guesthouses

    Southernmost Beach Resort and Guesthouses

    1319 Duval Street Key West FL
    $345 nightly
    The price is $389 total per night from Jan 13 to Jan 14
    $389 total
    Jan 13 - Jan 14, 2026
    Total with taxes and fees
    8.6/10 Excellent! (2,924 reviews)

Sugarloaf Key Guest Houses essential information

Accommodation
57 Guest Houses
Lowest Price
$187
Highest Price
$390
Popular accommodation
Amsterdam's Curry Mansion Inn, NYAH Key West - Adults Only, The Cabana Inn Key West - Adults Only, The Palms Hotel, Wicker Guesthouse, Heron House Court - Adult Only, Douglas House, Bishop Hotel Key West, Duval Inn

More to Explore