1
Alexander's Guesthouse
Guest house
Upscale, LGBT-only, conch-house-style guesthouse offering free breakfast & a pool.
4.90 (233 reviews)
2
Key West Bed and Breakfast
Bed & breakfast
Artsy rooms, individually decorated with tropical flair in a Victorian B&B with a hot tub & a sauna.
4.90 (146 reviews)
4
The Grand Guesthouse
Guest house
Laid-back guesthouse offering simple rooms with island-inspired decor, plus free breakfast & Wi-Fi.
4.80 (267 reviews)
5
Tropical Inn
Bed & breakfast
Laid-back lodging offering rooms in a historic house or garden cottages, plus a waterfall pool.
4.80 (238 reviews)
6
The Mermaid & The Alligator
Bed & breakfast
Posh B&B set in a refined Queen Anne-style home dating from 1904 with refined rooms & a plunge pool.
4.80 (178 reviews)
7
Key West Harbor Inn
Bed & breakfast
Laid-back, adults-only inn with an outdoor pool, plus free breakfast, Wi-Fi & happy hour.
4.80 (135 reviews)
8
The Conch House
Bed & breakfast
Dating to 1889, this B&B offers homey rooms, a pool & a breakfast spread that features mimosas.
4.80 (120 reviews)
9
Old Town Manor
Bed & breakfast
Refined rooms with a mix of traditional & contemporary decor, plus a patio area with a koi pond.
4.70 (263 reviews)
10
The Artist House
Indoor lodging
This landmark, arty guesthouse dates from the Victorian era & features a pool & daily happy hour.
4.70 (252 reviews)
11
Coco Plum Inn
Bed & breakfast
Cozy rooms in an airy B&B set in 2 Victorian houses, plus an outdoor pool & tropical gardens.
4.70 (190 reviews)
12
Knowles House
Bed & breakfast
Warm B&B in an 1860s clapboard house offering an outdoor pool & rooftop sundeck, plus free Wi-Fi.
4.70 (169 reviews)
13
The Duval House
Bed & breakfast
Casual B&B offering continental breakfast & an outdoor pool, plus tropical gardens.
4.60 (544 reviews)
14
Courtney's Place
Bed & breakfast
B&B offering relaxed cottages & rooms, some with kitchens, plus a pool & bike rentals.
4.60 (274 reviews)
15
Caribbean House
Bed & breakfast
Bright rooms with minifridges & free Wi-Fi in a laid-back hotel with a pastel-painted facade.
4.60 (267 reviews)
16
Ambrosia Key West
Bed & breakfast
Individually themed rooms & 2-bedroom cottages in a B&B with tropical gardens & 3 pools.
4.50 (211 reviews)
17
Seascape Tropical Inn
Bed & breakfast
Historic B&B featuring tropical-style quarters, a hot tub & continental breakfast with mimosas.
4.50 (121 reviews)
18
The Weatherstation Inn
Bed & breakfast
Upscale, island-influenced B&B in an elegant house dating from 1912 offering airy rooms & a pool.
4.50 (111 reviews)
19
La Pensione Inn
Bed & breakfast
Casual, adults-only B&B in a Victorian home offering 9 breezy, TV-free rooms, plus an outdoor pool.
4.40 (177 reviews)
20
The Inn on Fleming
Bed & breakfast
Charming 19th-century guesthouse with an outdoor pool, a tropical garden & free happy hour drinks.
4.40 (74 reviews)