A waterfront promenade with multi-story buildings, palm trees, and a clear blue sky.

Cottages in Monroe County

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Top Cities in Monroe County

A beach with clear water, palm trees, and people relaxing on the sand.
CottagesCottages

Marathon

Marathon
A beachside restaurant with white tables and chairs, palm trees, and a view of the sea.
CottagesCottages

Key Largo

Key Largo

Our top choices for Monroe County cottages

Exterior

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (349 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is AED 350
AED 910 total
includes taxes & fees
28 Jun - 29 Jun
Old Wooden Bridge Resort and Marina
Exterior

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (981 reviews)
"It was a very enjoyable stay, highly recommend."
United States
Andrea
The price is AED 349
AED 393 total
includes taxes & fees
28 Jun - 29 Jun
Tropical Cottages
Outdoor dining

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (187 reviews)
"Clean, great view, wonderful porch, comfortable bed"
United States
Karen H.
The price is AED 826
AED 1,679 total
includes taxes & fees
29 Jun - 30 Jun
Waterfront Home
Property grounds

Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
8.6 out of 10, Excellent, (203 reviews)
"It worked very well for us while we were there."
United States
Lori C.
Direct Oceanfront Cottage-Sunrise View- #2,
Exterior

Heart of Downtown Key West Cottage With Off-Street Parking

Heart of Downtown Key West Cottage With Off-Street Parking
Key West Historic District
10.0 out of 10, Exceptional, (163 reviews)
"Great location. Perfect for up to 4 adults. "
United States
Terry M.
Heart of Downtown Key West Cottage With Off-Street Parking
Exterior

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

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (166 reviews)
"Quite location, nice amenities and directions for check in/out were clear."
United States
Kasey M.
Cottage with Pool and Boat Dockage just minutes to Key West!
Beach

SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster

SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster
Summerland Key
9.6 out of 10, Exceptional, (44 reviews)
"Hope was wonderful, very helpful with places to eat and attractions. "
United States
Linda V.
SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster
Exterior

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

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (175 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Exterior

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

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (129 reviews)
"Good location, comfortable cabin.!"
United States
David C.
Charming cottages, dockage, pool, just minutes to Key West
Exterior

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (171 reviews)
"We had a nice stay at this property, which was clean and nicely presented. It is in a calm area by the water and has some good food options close by as well. We did use the pool on 2 days and it felt like a private pool just when we used it."
United Kingdom
Anish
Cottage with swimming pool and dockage, just minutes to Key West!
Property grounds

Conch Republic Consul General's Cottage.-Historic District

Conch Republic Consul General's Cottage.-Historic District
Old Town Key West
9.4 out of 10, Exceptional, (176 reviews)
"This place was great."
United States
Steve W.
Conch Republic Consul General's Cottage.-Historic District
Property grounds

Summer Discounts-Conch Republic Consul Cottage.-Pool-Historic District-Parking

Summer Discounts-Conch Republic Consul Cottage.-Pool-Historic District-Parking
Old Town Key West
9.2 out of 10, Wonderful, (87 reviews)
"We loved our stay at the Conch Republic … great location and serene neighborhood. It was quite musty at check-in though cleared up with windows open and fans on (Key West). The pool was a plus. Owner was awesome and we would definitely return. "
United States
Laurie C.
Summer Discounts-Conch Republic Consul Cottage.-Pool-Historic District-Parking
Exterior

~FLAMINGO COTTAGE~ 18+ Adult Only cottage near Duval St

~FLAMINGO COTTAGE~ 18+ Adult Only cottage near Duval St
Key West Historic District
9.4 out of 10, Exceptional, (11 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Highly recommend this property"
United States
Jessica C.
~FLAMINGO COTTAGE~ 18+ Adult Only cottage near Duval St
Exterior

Charming 1BR Cottage : Steps from Hemingway House & Old Town

Charming 1BR Cottage : Steps from Hemingway House & Old Town
Old Town Key West
Charming 1BR Cottage : Steps from Hemingway House & Old Town
Exterior

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (30 reviews)
"Great location, freshly renovated "
United States
Jackie M.
The price is AED 1,175
AED 2,174 total
includes taxes & fees
5 Jul - 6 Jul
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior

**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…

**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Key West Historic District
9.8 out of 10, Exceptional, (159 reviews)
"Perfect location and charming cottage. "
United States
Chris T.
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
3 bedrooms, WiFi, bed sheets, wheelchair access

Carpe' Diem Heart of the Fl. Keys Specials

Carpe' Diem Heart of the Fl. Keys Specials
Marathon
8.8 out of 10, Excellent, (153 reviews)
"Connie the host was excellent! Attended to our every need. Location is ideal. Nice quiet neighborhood. Very well supplied with extra items. Towels, beach chairs. Toiletries, etc.Perfect for fishermen!A lovely vacation "
United States
Denise M.
Carpe' Diem Heart of the Fl. Keys Specials
Interior

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool

Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
3.0 star property
Key West Historic District
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
Exterior

Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach

Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach
Key Largo
9.8 out of 10, Exceptional, (24 reviews)
"Great location!"
United States
Aaron P.
Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach
Exterior

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
Cudjoe Key
8.6 out of 10, Excellent, (59 reviews)
"We loved the location of this property. It was mostly private and close enough to Key West to drive to town nightly while far enough away to have a pit j black sky at night to star gaze. We loved the semi private area. The house was just right for the two of us. We loved eating breakfast and doing devotions on the front porch each night. Susan was easy to work with and we felt very safe the whole time we were there. We utilized the heck out of those loungers by the water to do absolutely...
United States
Jennifer C.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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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Top Monroe County Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"This was such a fun place! It was hard to leave to go touring because there was the huge beautiful pool out our door, also yard games outside all day, foosball and pool and other games. We enjoyed doing many of the activities in the evenings, even got to the karaoke airstream! The staff is available anytime. The shuttle is so helpful and it runs late enough to stay in the old town much of the evening if you want. We weren’t sure if we’d prefer staying in the old town or a resort a little bit away, but we are very happy with our choice! (Mom and daughter, 64 & 35)"
Connie 3-night trip
Posted 11 hours ago
Blue Flamingo Resort Key West