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Check prices for these dates

Next weekend
Mar 7 - Mar 9
In two weeks
Mar 14 - Mar 16
In one month
Mar 28 - Mar 30
In two months
Apr 25 - Apr 27

Top Cities in Monroe County

South Beach featuring tropical scenes, general coastal views and a beach
CottagesCottages

Key West

Key West

Compare 207 Cottages in Monroe County with updated reviews, rates, and availability.

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (193)
"Everything about it was great"
The price is $301
includes taxes & fees
$279 per night
Mar 3 - Mar 4
Old Wooden Bridge Resort and Marina
Tropical Cottages
Exterior

Tropical Cottages

3.0 star property
8.4 out of 10, Very Good, (783)
"Good place. "
The price is $201
includes taxes & fees
$179 per night
Mar 2 - Mar 3
Tropical Cottages
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (42)
"This is our second year at one of these cottages. We love the complex and the location is great to get to many things. The cottage has everything you would need and is very clean. The host has been great to work with."
The price is $355
includes taxes & fees
$319 per night
Mar 27 - Mar 28
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.8 out of 10, Excellent, (61)
"The cabin and pool were perfect. Fantastic restaurants very nearby. Only thing I was a little disappointed in was the shoreline and fishing. No beach and very shallow water throughout the entire bay. I'd definitely stay here again, just plan on traveling if you're looking to catch any fish."
The price is $366
includes taxes & fees
$330 per night
Mar 10 - Mar 11
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (132)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!
Quaint cottage, pool, dockage just minutes to Key West!
Miscellaneous

Quaint cottage, pool, dockage just minutes to Key West!

9.0 out of 10, Wonderful, (132)
"It is what it is, only wish the furniture was not worn out. "
The price is $444
includes taxes & fees
$400 per night
Mar 4 - Mar 5
Quaint cottage, pool, dockage just minutes to Key West!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.2 out of 10, Wonderful, (67)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
The price is $463
includes taxes & fees
$417 per night
Mar 5 - Mar 6
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St
Outdoor dining

ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St

2.5 star property
9.4 out of 10, Exceptional, (39)
"The cottage was perfect for the 2 of us. The pool was great and the place was nicely secluded. We would definitely consider renting again !!"
ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Beach nearby

The Dancing Rooster: 2 Blocks from Duval in Old Town.

10.0 out of 10, Exceptional, (114)
"Great location"
The price is $824
includes taxes & fees
$743 per night
Mar 30 - Mar 31
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
A heated pool

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

10.0 out of 10, Exceptional, (22)
"Pleased with this property and the property manager. Five star. "
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
ROYAL POINCIANA COTTAGE - Quaint Old Town location
A heated pool

ROYAL POINCIANA COTTAGE - Quaint Old Town location

2.0 star property
9.6 out of 10, Exceptional, (38)
"Great property & location!"
The price is $829
includes taxes & fees
$747 per night
Mar 5 - Mar 6
ROYAL POINCIANA COTTAGE - Quaint Old Town location
Waterfront Cozy Cottage with Boat Ramp & Dock!
Property grounds

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (55)
"Great time, great place!"
Waterfront Cozy Cottage with Boat Ramp & Dock!
Waterfront Home
Terrace/patio

Waterfront Home

8.8 out of 10, Excellent, (155)
"I wasn't expecting a 140 resort fee due before proceeding past the gate guard. The gate guard's response to my puzzled look was, "You were aware of the resort fee, right?" The fee is likely (at least I hope) embedded in the TOS. Moving on. The property permits pets but walking one's dog is prohibited. The properties are so small that one must walk a dog. Knowing this property was on a canal with open water access, I was not surprised that it needed some TLC. I think, most folks rent this type...
Waterfront Home
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Exterior

Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)

10.0 out of 10, Exceptional, (11)
"Super cute bungalow surrounded by a beautiful lake. The location was perfect for us and super convenient to Key West! The staff was very friendly and very helpful. After hours check-in was very smooth. We will stay there again when we are in the area!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.4 out of 10, Very Good, (40)
"Nice place. "
The price is $444
includes taxes & fees
$400 per night
Mar 8 - Mar 9
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (76)
"Cute house with wonderful features. Covered deck was a nice place to enjoy a book and meal. The open design of the living room and kitchen made the cottage feel big. The Venture Out community is welcoming. It was an excellent atmosphere to walk and bike in a safe space."
Canal front, dockage, 2 bedroom, 2 bath
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Exterior

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (9)
"We arrived to a spotless cabana! The bed was perfect! Just awesome accommodations that I would definitely book again!!! Highly recommend- it was close to Key West but quiet and relaxing. And our pet stayed with us."
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Riley's Retreat - Venture Out 107
Outdoor dining

Riley's Retreat - Venture Out 107

8.6 out of 10, Excellent, (7)
"We would stay here again. Very clean. Kitchen well supplied. The beds could be more comfortable, but that could be a preference of bed type. The blinds in the bedrooms did not close completly so if you sleep late the light could be an issue. Itwasnt for us."
Riley's Retreat - Venture Out 107
Old Town Cottage House in Old Town Key West!
Exterior detail

Old Town Cottage House in Old Town Key West!

Old Town Cottage House in Old Town Key West!
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, microwave, oven, stovetop

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (217)
"We have traveled to KW every winter for several years. This place is by far the best combination of location and space. Will be back. "
The price is $632
includes taxes & fees
$569 per night
Mar 10 - Mar 11
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
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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