Guesthouses in Key West You’ll Love (Page 2)

Top-Rated Key West Guesthouses for Every Budget and Style!

Looking for a guesthouse in Key West (Florida)? Discover and compare a wide selection of cozy guesthouses, bed & breakfast and inns in Key West – perfect for solo travelers, couples, or families. Whether you’re planning a weekend getaway or an extended stay, you’ll find charming, affordable options that suit every travelers needs. From centrally located guesthouses near downtown to peaceful retreats close to the beach, explore accommodations that match your style and budget.

Easily browse photos, read guest reviews, and book the ideal guesthouse in Key West today.

We found 51 Guest-houses in Key West and the surrounding area (within 20 miles)

Courtney's Place Historic Cottages & Inn...

Guesthouse in Key West, Florida , 720 Whitmarsh Lane

Offering an outdoor pool, this historic Key West property is just 1 minutes’ walk from Duval Street.

Parking
Pets allowed
Family rooms
Outdoor pool
Swimming Pool

Fabulous 1167 Reviews 9.0

from $167.63 Show details »

Authors Key West Guesthouse

Guesthouse in Key West, Florida , 725 White Street

Authors Key West Guesthouse features free Wifi and rooms with air conditioning in Key West.

Family rooms
Outdoor pool
Swimming pool
Swimming Pool

Fabulous 980 Reviews 8.8

from $111.38 Show details »

New Orleans House - Gay Male Adult Guest...

Guesthouse in Key West, Florida , 724 Duval Street

Located above a nightclub on historic Duval Street in Key West, Florida, this gay male guest house features an outdoor swimming pool, a clothing-optio...

Parking
Restaurant
Bar
Fitness centre
Outdoor pool

Very good 163 Reviews 8.2

from $248.92 Show details »

Old Town Suites

Guesthouse in Key West, Florida , 517 Truman Avenue

Located in Key West, Florida, these furnished self-catering apartments feature free WiFi access.

Parking
Family rooms

Very good 430 Reviews 8.2

from $225.00 Show details »

The Garden House

Guesthouse in Key West, Florida , 329 Elizabeth St

Offering air-conditioned rooms in the Downtown Key West district of Key West, The Garden House is a 18-minute walk from South Beach.

Parking
Pets allowed
Breakfast in the room

Fabulous 289 Reviews 8.7

from $167.63 Show details »

Seaport Inn

Guesthouse in Key West, Florida , 329 William Street

Located in the heart of the historic Seaport District in Old Town, Seaport Inn features an outdoor pool and barbecue and is 1969 feet walk from Mallor...

Pets allowed
Family rooms
Outdoor pool
Swimming pool
Swimming Pool

Very good 188 Reviews 8.5

from $58.00 Show details »

Caribbean House

Guesthouse in Key West, Florida , 226 Petronia Street

Featuring free WiFi throughout this adult-only property, Caribbean House offers accommodations in Key West.

Parking
Breakfast in the room

Fabulous 330 Reviews 8.7

from $301.30 Show details »

Alexander Palms Court - No Hidden Resort...

Guesthouse in Key West, Florida , 715 South Street

Alexander Palms Court - No Hidden Resort Fees! enjoys a location in Key West, a 6-minute walk from Southernmost Point and 0.7 miles from Ernest Heming...

Parking
Family rooms
Outdoor pool
Swimming pool
Swimming Pool

Fabulous 762 Reviews 8.7

from $235.13 Show details »

Eden House

Inn in Key West, Florida , 1015 Fleming Street

Locally owned and operated since 1975, this art deco hotel offers relaxing amenities and first-rate services in the center of Old Town Key West, withi...

Parking
Restaurant
Bar
Sauna
Fitness centre

Fabulous 615 Reviews 8.8

from $173.27 Show details »

Southernmost Inn Adult Exclusive

Inn in Key West, Florida , 525 United Street

This adults only Key West resort is 1 minutes walk from Duval Street and 5 minutes walk from the Atlantic Ocean.

Outdoor pool
Swimming pool
Swimming Pool

Good 1315 Reviews 7.9

from $114.85 Show details »

Wicker Guesthouse

Inn in Key West, Florida , 913 Duval Street

Located one block from the Ernest Hemingway House and Museum in Key West, Florida, this guesthouse has a large tropical garden and an outdoor pool.

Parking
Pets allowed
Bar
Family rooms
Outdoor pool

Very good 2906 Reviews 8.0

from $279.54 Show details »

Paradise Inn - Adult Exclusive

Inn in Key West, Florida , 819 Simonton Street

Paradise Inn - Adult Exclusive is located in Key West and features landscaped grounds with brick paths and a lotus pond with koi and tropical turtles.

Parking
Outdoor pool
Swimming pool
Swimming Pool

Fabulous 767 Reviews 8.8

from $179.80 Show details »

Fitch Lodge - Key West Historic Inns

Inn in Key West, Florida , 1030 Eaton Street

Located in the heart of Old Town, a few blocks from the historic harbor and Ferry Terminal and walkable to many museums.

Pets allowed
Outdoor pool
Swimming pool
Swimming Pool

Very good 409 Reviews 8.1

from $162.05 Show details »

Seascape Tropical Inn

Inn in Key West, Florida , 420 Olivia Street

Located off Duval Street, this bed and breakfast is just 2 minutes walk from The Ernest Hemingway Home and Museum.

Parking

Fabulous 497 Reviews 8.7

from $314.58 Show details »

The Cabana Inn Key West - Adult Exclusiv...

Inn in Key West, Florida , 413 Appelrouth Lane

Located in Key West, Florida, The Cabana Inn Key West is an adults only inn that features a swimming pool, hot tub and a daily continental breakfast.

Parking
Outdoor pool
Swimming pool
Swimming Pool

Very good 894 Reviews 8.2

from $302.61 Show details »

Simonton Court Historic Inn & Cottages

Inn in Key West, Florida , 320 Simonton Street

Located in Key West, this Florida adult-only inn offers complimentary, light continental breakfast and free Wi-Fi access.

Parking
Outdoor pool
Swimming pool
Swimming Pool

Superb 1002 Reviews 9.1

from $201.38 Show details »

Douglas House

Inn in Key West, Florida , 419 Amelia Street

Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool...

Parking
Pets allowed
Allergy-free room
Outdoor pool
Swimming pool

Fabulous 2334 Reviews 9.0

from $184.51 Show details »

The Porch on Frances Inn - Adults Exclus...

Inn in Key West, Florida , 535 Frances St

Conveniently set in the Downtown Key West district of Key West, The Porch on Frances Inn - Adults Exclusive is located 1.1 miles from Higgs Beach, 1.1...