Search Monroe County Cottage Rentals from CA $141

Compare and save

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Top Cities in Monroe County

Featured Cottages in Monroe County

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (203)
"ENJOYED OUR STAY. BEDDING NEEDS ALOT OF IMPROVEMENT. ONE BEDROOM HAD AN OLD MATTRESS AND THE OTHER BED ONLY HAD A PAD OVER WOOD ! OUR HOUSEBOAT WAS OLDER AND NEEDED FLOOR REPAIRS. NICE PEOPLE, JIMMY HELPED WITH THE MARINA."
The price is CA $199
CA $367 total
includes taxes & fees
Apr 1 - Apr 2
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 CA $208
CA $233 total
includes taxes & fees
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 CA $215
CA $408 total
includes taxes & fees
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 CA $236
CA $437 total
includes taxes & fees
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 CA $319
CA $668 total
includes taxes & fees
Apr 5 - Apr 6
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)
"This location is great - easy to get to bight and Duval St. The interior was very clean. Good shower, good room lay out, good mattress. Like the two different entrances as I stayed with my sister's family which gave us privacy. Good prompt response from owner and staff. "
The price is CA $716
CA $1,173 total
includes taxes & fees
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 CA $141
CA $420 total
includes taxes & fees
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 CA $250
CA $494 total
includes taxes & fees
Apr 1 - Apr 2
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 CA $250
CA $524 total
includes taxes & fees
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 CA $250
CA $500 total
includes taxes & fees
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!"
The price is CA $336
CA $635 total
includes taxes & fees
Apr 1 - Apr 2
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 CA $250
CA $516 total
includes taxes & fees
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 CA $319
CA $667 total
includes taxes & fees
Apr 1 - Apr 2
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...
The price is CA $236
CA $462 total
includes taxes & fees
Apr 26 - Apr 27
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 CA $336
CA $608 total
includes taxes & fees
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 CA $322
CA $654 total
includes taxes & fees
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.
Don't see what you're looking for?
See all available properties in Monroe County
Save an average of 15% on thousands of hotels when you're signed in