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Top Cities in Monroe County

Compare 193 Cottages in Monroe County with updated reviews, rates, and availability.

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very Good, (187)
"Wonderful relaxing stay in a quiet houseboat with all the needed ammenities. Will be back"
The price is $245
includes taxes & fees
$229 per night
Jan 30 - Jan 31
Old Wooden Bridge Resort and Marina

Tropical Cottages

3.0 star property
8.4 out of 10, Very Good, (774)
"From the moment we opened the door, we felt welcomed. The room was spacious and had touches of hospitality from the bedding to the bureau with a coffee area. The roosters woke us early! We saw a manatee from the the dock outside. "
The price is $169
includes taxes & fees
$150 per night
Jan 30 - Jan 31
Tropical Cottages

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

9.0 out of 10, Wonderful, (40)
"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."
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

8.8 out of 10, Excellent, (58)
"Very nice location. Clean and we love the pool. Good communication with owner "
The price is $495
includes taxes & fees
$446 per night
Feb 19 - Feb 20
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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!

9.0 out of 10, Wonderful, (132)
"It is what it is, only wish the furniture was not worn out. "
The price is $475
includes taxes & fees
$428 per night
Feb 8 - Feb 9
Quaint cottage, pool, dockage just minutes to Key West!

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)

Waterfront Home

8.8 out of 10, Excellent, (154)
"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...
The price is $485
includes taxes & fees
$437 per night
Feb 21 - Feb 22
Waterfront Home

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (74)
"My husband loved fishing everyday and I enjoyed reading.The place was in a perfect location and had most of the comforts of home. There was no cleaning table for the fish big inconvenience and no light available. My issue is the lack of shade on the porch on the comfortable couch. It’s way too hot"
Canal front, dockage, 2 bedroom, 2 bath

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

10.0 out of 10, Exceptional, (111)
"It was really important for my group to be able to walk to the majority of the food and things. It was a great spot to do that from. Our only regret is we did not come during a time of year when the weather was touch warmer. "
The Dancing Rooster: 2 Blocks from Duval in Old Town.

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (54)
"Brother-in-law and I stayed for 3 nights for a quick fishing getaway. The property was perfect for our needs. The property manager was proactive and communicative. He even reached out the day of check-in to let us know an early check-in was available. The property was in a nice quiet area, but just close enough to Kiki's to hear the evening live music from the fantastic pier. Also, within walking distance to Kiki's for a quick bite and a drink after fishing.The property was extremely clean...
Waterfront Cozy Cottage with Boat Ramp & Dock!

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)

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

10.0 out of 10, Exceptional, (16)
"We were very happy with our stay at this property! It was perfect for a couple! A lot of the properties I looked at were two bedrooms and much more expensive. I was happy to find this one. The gated community was awesome and friendly. The communication with the manager was prompt and helpful. I read some of the reviews complaining about all the "rules". We had ZERO problems with all the rules in the Venture Out Community. It was so quiet and everyone was friendly. We will definitely...
The price is $482
includes taxes & fees
$434 per night
Jan 31 - Feb 1
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

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 $495
includes taxes & fees
$446 per night
Feb 26 - Feb 27
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

8.6 out of 10, Excellent, (37)
"Well located to visit Key West as well as other Keys both East and West. House needs some attention. "
The price is $359
includes taxes & fees
$323 per night
Feb 22 - Feb 23
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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!

Old Town Cottage House in Old Town Key West!

ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St

2.5 star property
9.2 out of 10, Wonderful, (37)
"We loved our stay here. It was quiet and serene. Great location. We were able to walk or bike easily to everything we wanted to do."
The price is $905
includes taxes & fees
$816 per night
Feb 25 - Feb 26
ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St

ROYAL POINCIANA COTTAGE - Quaint Old Town location

2.0 star property
9.6 out of 10, Exceptional, (38)
"Great property & location!"
The price is $877
includes taxes & fees
$790 per night
Feb 4 - Feb 5
ROYAL POINCIANA COTTAGE - Quaint Old Town location

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (169)
"It was kind of exciting. the cops showed up on the property and on the next door property to the North, there was a tree of stolen bouys and a stolen crab trap. It was quiet. there was a bit of a flood when it rained but within a day or 2 the water was gone. we had trouble opening the slider on the deck and I think there was moisture in the door. Hopefully we left it pretty clean. we had to be at the airport by 6:30. thank you, it was a wonderful stay. Patty "
Direct Oceanfront Cottage-Sunrise View- #2,
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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