Cottages in Florida Keys & Key West, FL
Cottages in Florida Keys & Key West, FL, from $250 a night. Book direct on each manager's site, no OTA fee.
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COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
Cottage · 1 bed · 2 bath · sleeps 4
Key West, FL
From $411 a night
- air conditioning
- car not required
- dining table
- dvd player
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
Cottage · 1 bed · 2 bath · sleeps 4
Key West, FL
From $411 a night
- air conditioning
- available in the cottage: wifi
- bedsheets provided
- deck or patio
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
Cottage · 2 bed · 2.5 bath · sleeps 2
Key West, FL
From $423 a night
- air conditioning
- barbecue grill
- bedsheets provided
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools
Cottage · 2 bed · 2 bath · sleeps 6
Key West
From $450 a night
Exact location
Book direct on Center Court Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Cottage · 1 bed · 1 bath · sleeps 2
Key West
From $478 a night
Exact location
Book direct on Center Court Key West
Starr's Suite - 2 person K Suite w/Private Spa!
Cottage · 1 bed · 1 bath · sleeps 2
Key West
From $478 a night
Exact location
Book direct on Center Court Key West
Sunset Suite-2 BR, K/Q, Pvt. Deck/Spa! 2 Pools
Cottage · 2 bed · 2 bath · sleeps 4
Key West
From $668 a night
Exact location
Book direct on Center Court Key West
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
Cottage · 4 bed · 2 bath · sleeps 28
Key West, FL
From $1,172 a night
- air conditioning
- barbecue grill
- car not required
- dining area
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Blue Duval walking distance to Duval St
Cottage · 2 bed · 2 bath · sleeps 6
Key West
From $1,200 a night
Exact location
Book direct on goodness.house
Jade Key Walking distance to Duval
Cottage · 2 bed · 2 bath · sleeps 6
Key West
From $1,200 a night
Exact location
Book direct on goodness.house
Poolside Cottage #411
Cottage · 4 bed · sleeps 4
Key West, FL
From $250 a night
- air conditioning
- available in the house: free wifi
- barbecue grill
- blender
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Key West Cockadoodle Cottage on Duval
Cottage · 2 bed · sleeps 14
Key West, FL
From $361 a night
- air conditioning
- bedsheets provided
- coin laundry
- dining area
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Poolside Cottage #412
Cottage · 4 bed · sleeps 4
Key West, FL
From $394 a night
- air conditioning
- available in the house: free wifi
- balcony
- barbecue grill
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval! Shared Pool
Cottage · 2 bed · sleeps 6
Key West, FL
From $692 a night
- air conditioning
- bedsheets provided
- free wifi
- in the city center
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Cottage · 1 bath · sleeps 37
Key West, FL
From $407 a night
- air conditioning
- coffee/tea maker
- cookware, dishware, and utensils
- dining area
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Heart of Downtown Key West Cottage With Off-Street Parking
Cottage · 1 bath · sleeps 2
Key West, FL
From $722 a night
- air conditioning
- bathtub
- coffee/tea maker
- cookware, dishware, and utensils
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.
Cottage · sleeps 44
Key West, FL
From $394 a night
- air conditioning
- barbecue grill
- bedsheets provided
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St
Cottage · sleeps 60
Key West, FL
From $507 a night
- air conditioning
- barbecue grill
- bedsheets provided
- coffee/tea maker
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Charming Cottage in Old Town
Cottage · sleeps 13
KeyWest, FL
From $257 a night
- air conditioning
- available in the cottage: wifi
- dryer
- heating
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK
Cottage · sleeps 39
Key West, FL
From $781 a night
- air conditioning
- available in the cabin: wifi
- barbecue grill
- coffee/tea maker
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Key West Caribbean Cottage - On Duval St w Private Pool
Cottage · sleeps 3
Key West, FL
From $1,172 a night
- air conditioning
- dining area
- dining table
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Stock Island
Cottage · 2 bed
Stock Island, FL
From $328 a night
- business facilities
- air conditioning
- restaurant & bar
- accessibility
City-level location
Book direct on Luxury Vacation Rentals Anywhere in the World
Bella Grand Premier Estate
Cottage · 5 bed · 5 bath · sleeps 10
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
Blue Porch Cottage
Cottage · 1 bed · 1 bath · sleeps 4
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- swimming pool
City-level location
Book direct on Key West Vacation Rentals
Caribbean Cottage ~ Duval Street Key West
Cottage · 2 bed · 2 bath · sleeps 6
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
Casa Bella Petite le Bleu
Cottage · 2 bed · 2 bath · sleeps 4
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
Hidden Story-Book Cottage
Cottage · 1 bed · 1 bath · sleeps 2
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
Island Cosmopolitan Cottage
Cottage · 3 bed · 2 bath · sleeps 6
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
Key West Island Village Cottage
Cottage · 2 bed · 1 bath · sleeps 6
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
Key West Wabi Sabi
Cottage · 4 bed · 3 bath · sleeps 8
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- swimming pool
City-level location
Book direct on Key West Vacation Rentals
Little Digs Key West
Cottage · 1 bed · 1 bath · sleeps 2
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
Old Town Caribbean Estate
Cottage · 10 bed · 7 bath · sleeps 21
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
Vintage Luxury Cottage On Duval
Cottage · 1 bed · 1 bath · sleeps 4
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- swimming pool
City-level location
Book direct on Key West Vacation Rentals
Sea Glass Cottage
Cottage · 2 bed · 2 bath
Marathon, MA
No nightly rate published
- cleanliness
- self check in / check out
- safety features
- fire extinguisher
Exact location
Book direct on Florida Keys Vacation Rentals in Marathon
Thompson Island Key West — Private Island Estate
Cottage · sleeps 20
Key West, FL
No nightly rate published
City-level location
Book direct on Thompson Island Key West
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How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-31 05:16 UTC. Prices and facts are whatever the manager published on their own site.