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Compare 59 Cottages in Fleming Key with updated reviews, rates, and availability.

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)

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

10.0 out of 10, Exceptional, (109)
"Our 3 bedroom, 2 bathroom bungalow accommodated the 5 of us perfectly. Kitchen had all that we needed, space to sit outside, and so close to the action on Duval St. "
The Dancing Rooster: 2 Blocks from Duval in Old Town.

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)

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, (215)
"Very clean. Could use some updating such as fresh paint. "
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (150)
"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

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

9.8 out of 10, Exceptional, (11)
"Our stay was wonderful! The room was perfect for our stay. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

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

10.0 out of 10, Exceptional, (125)
"The Cottage is lovely. Communication was seamless and Charlie at Last Key Realty was incredibly helpful arranging a seaplane trip to Fort Jefferson and a golf cart for Xmas light viewing. Private, quiet and the perfect location off Duvall. Thank you for a wonderful weekend. "
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…

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)

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

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

10.0 out of 10, Exceptional, (208)
"Loved the location, loved the property - it worked great for our group of 6 visiting Key West!"
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!

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!

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

Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only

3.0 star property
10.0 out of 10, Exceptional, (1)
"There are 3 things I would say could and should be better. 1) extra toilet paper. There was only one partial roll in each bathroom and one extra partial roll. 2) no shampoo/conditioner. 3) no directions to the pool. I had to call and find out where it was. For the amount you pay, you’d think those items would be available as there are everywhere else I’ve stayed. "
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only

Old Town Key West Cottage 3bed/2bath

10.0 out of 10, Exceptional, (1)
"We had an incredible stay in this house! We were very comfortable and constantly in contact with the host, who was always very communicative and helpful when we needed something. The location is perfect, just meters from the main street of Key West. The house was in perfect conditions and it’s just like the pictures! I 100% recommende it ☺️"
Old Town Key West Cottage 3bed/2bath

Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

3.0 star property
9.0 out of 10, Wonderful, (4)
"The unit had fun and stylish decor. Bed was comfy and I’m picky. The steeps are a challenge- always forgetting there is one more step. Was concerned about the noise in the back from a restaurant or bar- but when doors closed you can’t hear it. And there is no noise later in the evening. One suggestion- some nightlights for the night for Safety. We will be back. Great experience "
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool

BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!

10.0 out of 10, Exceptional, (2)
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!

Colorful cottage w/shared pool, central AC, washer/dryer

Colorful cottage w/shared pool, central AC, washer/dryer

PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!

9.6 out of 10, Exceptional, (14)
"Great location good layout but outdated and for the price paid should be more up to date. The bed was very uncomfortable and the pillows were subpar but the interaction with the management was amazing"
PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!

Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

3.0 star property
10.0 out of 10, Exceptional, (4)
"Great condo ! A little dated but was just perfect for our family of 4. Wonderful pool and hot tub and walking distance to Smathers Beach and some local convenience stores. Highly recommend ! "
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
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, (112)
"We loved staying on the houseboat."
The price is AED 559
AED 1,145 total
includes taxes & fees
28 Jan - 29 Jan
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (361)
"Fun little place with a great pool. Ken was very helpful in all aspects. Highly recommended. Be aware its a small place but very comfortable."
The price is AED 657
AED 1,255 total
includes taxes & fees
3 Feb - 4 Feb
Steps from Duval, Pool on Site & Bikes Included!

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (30)
"We had a wonderful time. It is an older, smaller boat but we enjoyed it. There is a port a pot in the cabin but there is a huge shower and bathroom under the carport. We were able to fish right off the boat. Frank will answer texts pretty quickly. "
34’ Catamaran Sailboat
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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