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Compare 49 Cottages in Florida Keys with updated reviews, rates, and availability.

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (222)
"Lovely, quiet place on the water with plenty of space in the houseboat"
The price is $256
includes taxes & fees
$239 per night
Apr 30 - May 1
Old Wooden Bridge Resort and Marina

Tropical Cottages

3.0 star property
8.4 out of 10, Very Good, (805)
"It was verry cozy!"
The price is $146
includes taxes & fees
$130 per night
May 1 - May 2
Tropical Cottages

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

8.6 out of 10, Excellent, (135)
"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!

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

8.8 out of 10, Excellent, (155)
"Place was very clean. The property is in need of upkeep and updating. It was hit in the last hurricane. "
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

8.6 out of 10, Excellent, (37)
"Word can not explain the place everything was the best and would stay again and again "
The price is $270
includes taxes & fees
$243 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, (140)
"We had a wonderful time at your place. Thank you for having us, we loved the Keys!"
The price is $348
includes taxes & fees
$314 per night
May 1 - May 2
Cottage with Pool and Dockage, just minutes to Key West

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

9.0 out of 10, Wonderful, (73)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
The price is $368
includes taxes & fees
$332 per night
May 9 - May 10
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

9.4 out of 10, Exceptional, (23)
"Lovely, quiet property. I really enjoyed my stay. Pool was heated. Wonderful place to relax under the stars."
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (174)
"Very comfortable and clean place right by water, had a great stay "
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, (39)
"It's a good quiet place about 20 miles from Key West. The property itself has seen its best years-- it has aged now but functional. The entrance is a bit tricky to find, right off of the highway. Overall a good place if you don't mind driving back and forth between Key West attractions. "
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, (68)
"Place was everything we needed, would definitely stay again "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

8.6 out of 10, Excellent, (115)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
Charming cottages, dockage, pool, just minutes to Key West

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

9.0 out of 10, Wonderful, (135)
"It is what it is, only wish the furniture was not worn out. "
Quaint cottage, pool, dockage just minutes to Key West!

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (81)
"Excellent appearance, location, amenities and comfort. Bedrooms are a little tight but manageable. Host was very responsive and easy to work with. "
Canal front, dockage, 2 bedroom, 2 bath

Beautiful Modern House in Key Largo

10.0 out of 10, Exceptional, (42)
"My brother and me stayed 3 nights on a Harley Trike trip in the Keys, great place to stay. Highly recommend!"
The price is $601
includes taxes & fees
$541 per night
Apr 30 - May 1
Beautiful Modern House in Key Largo

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

9.0 out of 10, Wonderful, (145)
"We had a wonderful stay in a small cottage in Cudjoe Key. It was a fun little place stay. Location was great for visiting the other Keys. I would seriously look at staying in one of the bigger cottages if I brought my family down. Thank you very much!"
The price is $285
includes taxes & fees
$257 per night
May 30 - May 31
Cottage with swimming pool and dockage, just minutes to Key West!

STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!

9.6 out of 10, Exceptional, (51)
"Clean, convenient, great host. Would definitely stay again! Especially enjoyed the daily pastries!!"
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!

ISLE BE BACK To The Sunny Keys

9.6 out of 10, Exceptional, (30)
"Had a great time with family for mini season. Would definitely rent again. Beautiful place and plenty of room!"
ISLE BE BACK To The Sunny Keys

35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

9.8 out of 10, Exceptional, (128)
"We had a great time, there for lobstering. Very clean place, great location!"
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

Waterfront Home

8.8 out of 10, Excellent, (161)
"First, you walk into the property through a bedroom. Stupid. The screen doors in the front and back kept falling off the tracks. 4 very old bath towels which meant washing constantly. The overall feel was that the place was old. Shower faucet in the one bathroom was ready to come off the wall. And the smell off the canal was the most disgusting smell - I can’t even describe it."
Waterfront Home
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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Other property types in Florida Keys

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (222)
"Lovely, quiet place on the water with plenty of space in the houseboat"
The price is $256
includes taxes & fees
$239 per night
Apr 30 - May 1
Old Wooden Bridge Resort and Marina

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (461)
"Great location, clean, room was modern with everything you need, nice pool area and beautiful views... Perfect stay for a family!!"
The price is $182
includes taxes & fees
$163 per night
May 4 - May 5
Breezy Palms Resort

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1179)
"Mid way thru the Keys was a plus. It's off season, but everything was very good, and we see that they are working to make the experience even better for the busy season. We'd definitely stay again!"
The price is $282
includes taxes & fees
$251 per night
Apr 30 - May 1
Skipjack Resort & Marina
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.