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Browse Select Key West Cottages

Southernmost Retreat: 2 Blocks from Duval in Old Town.
Located in Key West Historic District, this cottage is within a 10-minute walk of Duval Street, South Beach, and Key West Butterfly and Nature Conservatory. ...
5/5Exceptional! (24 reviews)
love it!
"absolutely loved staying here! we were able to walk everywhere, clean & cozy, and Scott & Nancy are wonderful people. will most definitely be back!"

Reviewed on Sep 11, 2021

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Southernmost Retreat: 2 Blocks from Duval in Old Town.
Simonton Court Cottages
3.5 out of 5
910 Simonton, Key West, FL
Located in Key West Historic District, this cottage is within a 10-minute walk of Duval Street, South Beach, and Key West Butterfly and Nature Conservatory. ...
3.6/5Good! (15 reviews)
Everything you’d need
"This place is a gem. The management called before and during our trip to make sure everything was going well. The cottage was clean, quaint, and walkable to everything in Key West. Even though parking wasn’t available onsite, we easily found parking yards away from the entrance for our two night ..."

Reviewed on May 27, 2021

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Simonton Court Cottages
OSPREY - Cozy Private Cottage in Gated Compound, Large Shared Pool + Patio
Located in Key West Historic District, this cottage is within a 15-minute walk of Duval Street and Southernmost Point. Nancy Forrester's Secret Garden and Ernest ...
4.6/5Wonderful! (27 reviews)
Great apartment for vacation
"The location is great, walking distance from Duval Street. I am from NYC so I’m used to very small studios, this was not the case. It was very spacious perfect rental for 2. The only down fall for me was the check in and check out process. Check out is very early 10AM, you have to walk the keys over ..."

Reviewed on Jul 15, 2021

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OSPREY - Cozy Private Cottage in Gated Compound, Large Shared Pool + Patio
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Downtown Cottage just off famous Duval Street-No Contact Check-In
Located in Key West Historic District, this historic cottage is within a 15-minute walk of Duval Street and Southernmost Point. Key West Butterfly and Nature ...
4.6/5Wonderful! (63 reviews)
Centrally located home away from home.
"Beautiful location in Key West. Property was well kept, clean pool surrounded by greenery. The Carriage house was welcoming and quaint. We will visit again!"

Reviewed on Sep 9, 2021

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Downtown Cottage just off famous Duval Street-No Contact Check-In
Sea Breeze Cottage in Truman Annex Location! Location! Location!
Located in Old Town Key West, this historic cottage is within a 15-minute walk of Duval Street and Southernmost Point. Florida Keys Eco - Discovery Center and ...
4.9/5Exceptional! (87 reviews)
Perfect location
"My family had a wonderful time,location was perfect walking distance to everything. Cottage was clean with everything in working order. I would definitely rent this again."

Reviewed on Sep 14, 2021

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Sea Breeze Cottage in Truman Annex Location! Location! Location!
Vintage Luxury Cottage on Duval
Located in Key West Historic District, this cottage is within a 5-minute walk of Duval Street, South Beach, and Key West Butterfly and Nature Conservatory. Southernmost ...
4.7/5Exceptional! (19 reviews)
Great getaway cottage
"Nice, cozy cottage for our vacation. Very clean."

Reviewed on Nov 22, 2020

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Vintage Luxury Cottage on Duval
~ Chick-A-Pea Cottage ~ Breathtaking Home w/ Pool & Parking, 1 Block to Duval
Located in Key West Historic District, this cottage is within a 10-minute walk of Duval Street and Southernmost Point. Key West Lighthouse and Keeper's Quarters ...
4.9/5Exceptional! (34 reviews)
Great service and beautiful cottage
"The pictures don't really do this place justice - especially the yard. The property manager was incredibly responsive and the location is incredible - near to everything but still quiet and private."

Reviewed on Sep 16, 2021

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~ Chick-A-Pea Cottage ~ Breathtaking Home w/ Pool & Parking, 1 Block to Duval
Simonton Court Cottages
3.5 out of 5
910 Simonton Street, Key West, FL
Located in Key West Historic District, this cottage is within a 5-minute walk of Duval Street and Ernest Hemingway Home and Museum. South Beach and Key West ...
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Simonton Court Cottages
Your Private Oasis in Old Town Key West - The Cigar Maker's Tropical Cottage!
Located in Key West Historic District, this historic cottage is within 1 mi (2 km) of Duval Street and Southernmost Point. Higgs Beach and Key West Butterfly ...
4.7/5Exceptional! (7 reviews)
Lovely neighbors. Had fun, but the property is not up to standard for what I paid. Only one bathroom
"Very expensive for the property. Needs some updating."

Reviewed on Apr 15, 2021

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Your Private Oasis in Old Town Key West - The Cigar Maker's Tropical Cottage!
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Located in Key West Historic District, this historic cottage is within 1 mi (2 km) of Duval Street and Southernmost Point. Key West Film Society and Heritage ...
5/5Exceptional! (57 reviews)
Wonderful
"This property was just perfect, very clean, quiet, and the location was just wonderful! You could walk to so many places to eat or shop. Would stay there anytime we come to Key West."

Reviewed on Aug 14, 2021

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**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
TRANQUILITY - Quaint Cottage in Gated Compound with Shared Pool + Private BBQ
Located in Key West Historic District, this cottage is within a 15-minute walk of Duval Street and Southernmost Point. Nancy Forrester's Secret Garden and Ernest ...
4.8/5Exceptional! (53 reviews)
Great Experience!
"My husband and I had a great experience staying in the Tranquility Cottage! The Colony Cottages are conveniently located within walking distance to most things, but a few blocks off Duval, which provides a nice separation from the hustle and bustle. We rented a scooter during our stay. There are ..."

Reviewed on Sep 1, 2021

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TRANQUILITY - Quaint Cottage in Gated Compound with Shared Pool + Private BBQ
CASITA DE CATHERINE Cozy One Bedroom Private Home with Hot Tub, Pet Friendly
Located in Key West Historic District, this cottage is within a 10-minute walk of Duval Street and Southernmost Point. Key West Butterfly and Nature Conservatory ...
5/5Exceptional! (5 reviews)
Quaint house, great location.
"Really enjoyed staying here and would highly recommend it."

Reviewed on Sep 17, 2021

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CASITA DE CATHERINE Cozy One Bedroom Private Home with Hot Tub, Pet Friendly
Starfish  Cottage
Key West, FL
Located in Key West Historic District, this cottage is within a 15-minute walk of Duval Street and Southernmost Point. Nancy Forrester's Secret Garden and Ernest ...
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Starfish Cottage
3 blocks from waterfront and 1 block off Duval in Old Town Key West
Located in Key West Historic District, this historic cottage is within 1 mi (2 km) of Duval Street and Southernmost Point. Key West Film Society and Heritage ...
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3 blocks from waterfront and 1 block off Duval in Old Town Key West
Dog-friendly getaway in a quiet, residential neighborhood w/ a shared pool
Located in Old Town Key West, this cottage is within 1 mi (2 km) of Simonton Beach and Southernmost Point. Duval Street and South Beach are also within 5 ...
4.6/5Wonderful! (32 reviews)
We will be back
"Great location and a beautiful home always something to do amazing food memories priceless"

Reviewed on Jun 14, 2021

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Dog-friendly getaway in a quiet, residential neighborhood w/ a shared pool
Sandcastle Cottage
Key West, FL
Located in Key West Historic District, this cottage is within a 15-minute walk of Duval Street and Southernmost Point. Ernest Hemingway Home and Museum and Key ...
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Sandcastle Cottage
Old Town Key West Cottage
Located in Old Town Key West, this cottage is within a 5-minute walk of Duval Street and Southernmost Point. Key West Lighthouse and Keeper's Quarters Museum ...
4.6/5Wonderful! (10 reviews)
Location, Location, Location
"Cozy studio/cottage in GREAT location. Pool is awesome. Beach close. Duval street close. Owner: Owen was easy to talk to and accommodating."

Reviewed on Mar 2, 2020

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Old Town Key West Cottage
Tropical Jewel in Historic Seaport - 2BR/2BA - Pool - Monthly Rental
Located in Key West Historic District, this cottage is within 1 mi (2 km) of Duval Street and Southernmost Point. Nancy Forrester's Secret Garden and Schooner ...
5/5Exceptional! (1 review)
Our slice of Heaven .....
"Loved the Tropical Jewel -- location, pool, the privacy, the yard!"

Reviewed on Apr 14, 2019

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Tropical Jewel in Historic Seaport - 2BR/2BA - Pool - Monthly Rental
Casa Manana Key West Monthly: 2  BR, 2  BA Cottage in Key West, Sleeps 6
Located in Midtown, this cottage is 0.8 mi (1.3 km) from Higgs Beach and 1.6 mi (2.5 km) from Southernmost Point. Simonton Beach and Duval Street are also within ...
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Casa Manana Key West Monthly: 2 BR, 2 BA Cottage in Key West, Sleeps 6
Butterfly Cottage
Key West, FL
Located in Key West Historic District, this cottage is within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. South Beach and Southernmost ...
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Butterfly Cottage
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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.

Other property types in Key West

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2.5 out of 5
3101 N. Roosevelt Blvd, Key West, FL
The price is $119 per night from Sep 23 to Sep 23
3.9/5Very Good! (1,869 reviews)
"Breakfast was nice, lots of variety. Grounds were scenic, beautiful views of the bay!"

Reviewed on Sep 20, 2021

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Hilton Garden Inn Key West,The Keys Collection

Hilton Garden Inn Key West,The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
The price is $141 per night from Sep 27 to Sep 27
3.9/5Very Good! (980 reviews)
"Very convenient, nice pool/hot tub area. The bartender at the pool bar was very accommodating. Would love to stay again."

Reviewed on Sep 18, 2021

Hilton Garden Inn Key West,The Keys Collection
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd, Key West, FL
The price is $175 per night from Sep 26 to Sep 26
4.3/5Excellent! (1,308 reviews)
"Clean , centric to everything, clean. Nice property"

Reviewed on Sep 18, 2021

Hampton Inn Key West FL
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.

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