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Top Cities in Monroe County

Compare 249 Cottages in Monroe County with updated reviews, rates, and availability.

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (203)
"Great boat cabin. Definitely recommend it. Will visit again. Thanks"
The price is $256
includes taxes & fees
$239 per night
Apr 2 - Apr 3
Old Wooden Bridge Resort and Marina

Tropical Cottages

3.0 star property
8.4 out of 10, Very Good, (790)
"This was an excellent choice. We arrived at 10 pm and the directions sent before checking in were perfect. Had absolutely no trouble and the grounds were very well taken care of. Super cute cottages and very comfortable."
The price is $163
includes taxes & fees
$145 per night
Apr 3 - Apr 4
Tropical Cottages

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (119)
"This cottage was amazing for so many different reasons. Location, quiet, and detail to guests needs. Marcela was a great communicator. No need to communicate too much, everything worked great! We are returning next year!"
Heart of Downtown Key West Cottage With Off-Street Parking

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

8.6 out of 10, Excellent, (133)
"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!"
The price is $279
includes taxes & fees
$251 per night
Apr 8 - Apr 9
Cottage with Pool and Boat Dockage just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

8.8 out of 10, Excellent, (151)
"Cottage 1 was right by the water. A walk down a long path to a dock was a nightly trip to watch the sunset. Located between Marathon Key and Key West was perfect for restaurants and stores without the crowding from tourists. About 20-30 minutes to Key West"
The price is $298
includes taxes & fees
$268 per night
Apr 7 - Apr 8
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

9.8 out of 10, Exceptional, (6)
"Great location, very helpful staff "
The price is $389
includes taxes & fees
$353 per night
Apr 6 - Apr 7
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

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

10.0 out of 10, Exceptional, (116)
"Clean, perfect location in Old Town Key West. The property manager was so accommodating and quickly got back to me with answers to my questions. Would definitely stay there again. "
The price is $814
includes taxes & fees
$733 per night
Apr 6 - Apr 7
The Dancing Rooster: 2 Blocks from Duval in Old Town.

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

8.6 out of 10, Excellent, (32)
"Property was clean. There were some small ants in the kitchen and bath."
The price is $289
includes taxes & fees
$259 per night
Apr 30 - May 1
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (135)
"Very nice"
The price is $425
includes taxes & fees
$383 per night
Apr 12 - Apr 13
Cottage with Pool and Dockage, just minutes to Key West

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

9.2 out of 10, Wonderful, (68)
"Beach towels!! The cottage is very cute. Very basic kitchen supplies and bathroom supplies. No extra comfort amenities...travel mugs, beach chairs, hot pads for kitchen, toilet paper, beach towels. And if you plan to wash anything bring coins. 1.50 per wash "
The price is $366
includes taxes & fees
$330 per night
Apr 6 - Apr 7
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

SEA SHELL COTTAGE UNIT #2 Sleeps 2

9.4 out of 10, Exceptional, (19)
"We stayed in the sea shell cottage, perfect for two. The unit was clean and the grounds were beautiful. There is a grill and a flattop griddle you can use. We went out for most meals so we didn’t use them. Close to a ton a restaurants, good recommendations in the book Had a great time! Will be back"
SEA SHELL COTTAGE UNIT #2 Sleeps 2

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (171)
"The location and views are great. It was a comfortable stay. There were some deferred maintenance items which were shared with the property manager. Completion of these items will greatly enhance the experience at the property and make it a '10' rating."
The price is $349
includes taxes & fees
$315 per night
Apr 9 - Apr 10
Direct Oceanfront Cottage-Sunrise View- #2,

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

8.0 out of 10, Very Good, (37)
"This rental is in a perfect, peaceful location! We brought our paddleboards and fishing poles and enjoyed the Florida sun. Great getaway - we will definitely be back!"
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, (64)
"These are great older cottages. Not luxurious, great for fishing, relaxing away from the bustle of Key West but a short drive to all the fun. Local restaurants are great Tonio's was definitely our favorite. Lobster and local fish. Skewered shimp with rice and great sauce. We had a relaxing time "
The price is $360
includes taxes & fees
$324 per night
Apr 7 - Apr 8
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

9.4 out of 10, Exceptional, (8)
"We really enjoyed our recent long weekend at the Seagull property! It started with an airport pickup from Wisi, who also picked up our bags after checkout so that we could walk around before our flight. And then he came and met us where we were to run us to the airport-it was fantastic! The property is great, albeit a 10-20 min walk to some places. That said, the quiet was great and the Tipsy Rooster across the street alwyas had great live music at night! It was a great fit for us, although...
The price is $388
includes taxes & fees
$352 per night
Apr 2 - Apr 3
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (109)
"We launched our kayaks right from the property and found great fishing and paddling moments from the dock. The bay and dockage are very shallow--I wouldn't bring my power boat to this property. Easy drive into Key West and to all the lower keys. Nice little grocery store within minutes had everything we needed. The property is older and could use some maintenance, but if you don't mind a little fraying at the edges, this is a comfortable, beautiful and quiet corner of the keys. We loved...
Charming cottages, dockage, pool, 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 $425
includes taxes & fees
$383 per night
Apr 19 - Apr 20
Quaint cottage, pool, dockage just minutes to Key West!

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (79)
"We really liked the location of this rental. It is situated in a quiet community, on the beautiful canal, and close to other things in the area. We did not spend a ton of time at the house due to family events but the property had everything we needed for our short weekend trip. The only reason I gave it a 4 star is because of the air conditioning rule. The house rules state you cannot turn the AC down lower than 75 degrees, which is not a comfortable setting. "
The price is $451
includes taxes & fees
$406 per night
Apr 5 - Apr 6
Canal front, dockage, 2 bedroom, 2 bath

HIDDEN OASIS 3 blocks from Duval

2.5 star property
9.4 out of 10, Exceptional, (86)
"Great location, loved the pool and outdoor patio"
HIDDEN OASIS 3 blocks from Duval

Get your ISLAND STLYE on!

2.0 star property
9.6 out of 10, Exceptional, (77)
"Easily walkable to most tourist attractions."
Get your ISLAND STLYE on!
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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