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Compare 50 Cottages in Fleming Key with updated reviews, rates, and availability.

ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St

2.5 star property
9.4 out of 10, Exceptional, (38)
"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 AED 1,172
AED 3,068 total
includes taxes & fees
25 Feb - 26 Feb
ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St

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

10.0 out of 10, Exceptional, (114)
"Great location"
The Dancing Rooster: 2 Blocks from Duval in Old Town.

ROYAL POINCIANA COTTAGE - Quaint Old Town location

2.0 star property
9.6 out of 10, Exceptional, (38)
"Great property & location!"
The price is AED 1,172
AED 3,068 total
includes taxes & fees
5 Mar - 6 Mar
ROYAL POINCIANA COTTAGE - Quaint Old Town location

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)

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)

Old Town Cottage House in Old Town Key West!

Old Town Cottage House in Old Town Key West!

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (217)
"We have traveled to KW every winter for several years. This place is by far the best combination of location and space. Will be back. "
The price is AED 1,179
AED 2,314 total
includes taxes & fees
24 Feb - 25 Feb
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

9.6 out of 10, Exceptional, (8)
"Rick's place is the perfect location to get around old town Key West. Walkable to bars, restaurants, activities. Bar across the street has live music afternoon and evenings. The best perk - Rick and staff shuttled us to and from the airport and made sure that we had transportation when we had car rental issues. He made it known that he and staff were available for transport as needed. Thank you Rick!!!!"
The price is AED 1,315
AED 2,405 total
includes taxes & fees
9 Mar - 10 Mar
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (151)
"My aunts, mom and I had a great stay. The rooms were spacious, allowing plenty of space for the 5 of us to spread out. Roberta and the owner were very kind. I am hoping to get my husband to come back for a visit with me. "
Conch Republic Consul General's Cottage.-Historic District

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

10.0 out of 10, Exceptional, (127)
"This property is awesome! You will never find a better location to stay than this. 15 steps from the heart of Duval St. Two big rooms with lots of privacy and every amenity you can ask for. We will definitely be returning. "
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

9.8 out of 10, Exceptional, (12)
"Great spot. Very quiet and clean. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex

10.0 out of 10, Exceptional, (185)
"Loved our stay , perfect layout with everything we needed. Quiet location in Truman Annex. Hope to stay next year! "
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex

Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

10.0 out of 10, Exceptional, (5)
"Took my grandmother on her bucket list trip. Great location and set up for myself, my mom and grandmother!"
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (4)
"Located close to many activities. The place was so clean and private. Beds were comfortable. Had everything needed for my visit. Highly recommend staying here."
The price is AED 1,315
AED 2,405 total
includes taxes & fees
9 Mar - 10 Mar
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Margarita Cottage ~ Popular island retreat

2.0 star property
9.6 out of 10, Exceptional, (37)
"Loved our stay at the Margarita Cottage. Walked all over Key West from very central location. Heated Pool was a plus - even for a mid December dip!"
Margarita Cottage ~ Popular island retreat

~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!

10.0 out of 10, Exceptional, (211)
"This was the best vacation house absolutely Pristine clean the outdoor space amazing. The warm pool was perfect excellent location it was a dream vacation for my surprise 60th birthday with my family 7 of us plenty of space !"
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay at this spacious Key West rental! The location is perfect—close to Duval Street but far enough from the hustle and bustle to enjoy some peace and quiet. The space was clean, comfortable, and well-maintained. The host was fantastic and very accommodating.One thing to note is that there’s no dedicated parking, but there is street parking nearby and a paid parking lot just two blocks away. Overall, it was a great stay, and I would definitely book again!"
The price is AED 1,315
AED 2,405 total
includes taxes & fees
9 Mar - 10 Mar
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

OSPREY STUDIO @ The Colony-Sleeps up to 4

2.0 star property
9.4 out of 10, Exceptional, (51)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
OSPREY STUDIO @ The Colony-Sleeps up to 4

Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only

3.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I loved our stay at Linger Longer. We hadeverything we needed for a top notch vacation. Beds and couch were very comfortable. The pool was great. We were able to relax and unwind."
Linger Longer by Avantstay Key West Walkable Gated Community, Shared Pool Week Long Stays Only

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 star property
8.0 out of 10, Very Good, (2)
"The living room furniture and mattresses are not the most comfortable. Worn. Mattresses in small bedroom need replacement. Air conditioner does not reach small bedroom. "
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
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 Fleming Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (117)
"Awesome place, with a cool location right near the mangroves. Has a little restaurant and bar and gift shop, as well as kayak tours and rentals. Paddle boards too. We liked the visits from the manatees and nurse sharks near the fish cleaning station. Only negatives I have are that the ceiling fan chains were broken and harder to reach, some of the pillows were a bit yellowish and have seen better days and multiple devices like the Air conditioner and TV remotes batteries were dead, but they...
The price is AED 757
AED 1,368 total
includes taxes & fees
25 Feb - 26 Feb
Aqua Lodges at Hurricane Hole Marina

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (803)
"Great location, clean, and good customer service. wish they had fishing rods and more to do around the property, and the AC didn't keep the upstairs cool, very hot up there at night. overall, happy about the stay."
Coconut Mallory Resort And Marina By Kees Vacations

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (371)
"2nd time staying here. Clean and close to everything. Great stay"
The price is AED 474
AED 1,019 total
includes taxes & fees
6 Mar - 7 Mar
Steps from Duval, Pool on Site & Bikes Included!
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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