Search Fleming Key Cottages

    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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Fleming Key Cottages

Southernmost Retreat: 2 Blocks from Duval in Old Town.
Beach nearby
Southernmost Retreat: 2 Blocks from Duval in Old Town.
10.0 out of 10, Exceptional, (100)
"This place was in a perfect location. It was a easy walk to Duval and to many of the bars and restaurants. The operating manager responded quickly to a couple of minor issues that we had. I would definitely stay there again."
The price is £663
includes taxes & fees
26 Jun - 27 Jun
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Old Town Cottage House in Old Town Key West!
Exterior
Old Town Cottage House in Old Town Key West!
Old Town Cottage House in Old Town Key West!
Conch Republic Consul General's Cottage.-Historic District
Pool
Conch Republic Consul General's Cottage.-Historic District
9.4 out of 10, Exceptional, (140)
"The cottage was exactly as described. The unit was far enough from the action for a quiet nights rest but a close walk to Duval to enjoy all the action. The pool was very nice and clean, and the resident cat was just an added bonus."
Conch Republic Consul General's Cottage.-Historic District
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
Exterior
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
10.0 out of 10, Exceptional, (119)
"Perfect location. Everything you need. Nice decor. Very quiet. Alice was very helpful. My only complaint is not being allowed in the huge pool that sat unused the whole time we had to walk by it to get to our rooms. It was hot while we were there and it would have been hospitable."
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Pool | A heated pool
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
10.0 out of 10, Exceptional, (196)
"This beautifully decorated property is centrally located but feels secluded. The beds are incredibly comfortable and the pool was perfect for relaxing. It was perfect for our girls' weekend. The property manager was attentive and helpful. We would definitely stay here again."
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
Interior
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
3.0 star property
10.0 out of 10, Exceptional, (1)
Coral Villa by Avantstay Close 2 DT Key West Shared Pool & Patio!
Key West Found by Avantstay Close to Shops w/ Patio & Shared Pool! Week Long Stays Only
Interior
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
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (204)
"We stayed in cabin 6 for a week. Management was very helpful. The cabin had everything we needed. Very comfortable bed and the 2 baths were definitely a plus. Great location. Within walking distance to everything. We did rent a golf cart and parking was never a problem. We are planning our next trip and will stay here again."
The price is £312
includes taxes & fees
24 Jun - 25 Jun
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Property grounds
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
9.8 out of 10, Exceptional, (7)
"We stayed here as a family of 4, so cute, clean and quiet! Loved it!"
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Property grounds
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
9.8 out of 10, Exceptional, (8)
"I couldnt have spent my 40th birthday in any other place. The bungalow and property was perfect. No issues with water or power supply,cold ac after the long hot days out in key west. I told my other half i could live in one of those clean nicely built bungalows...it was PERFECT!"
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
Interior
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
4.5 star property
10.0 out of 10, Exceptional, (3)
"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
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Property grounds
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
10.0 out of 10, Exceptional, (9)
"Perfect size for a couple. New and clean, couldn’t be happier, thanks!"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!
Fridge, microwave, oven, stovetop
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!
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Property grounds
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
10.0 out of 10, Exceptional, (2)
"This is a nice property. The accommodations were large enough for my family. The indoor space was clean and nicely appointed. The outdoor space was ok. Due to how close the units are together you are right next to your neighbors car when sitting on the patio. The location is about 20 miles from Key West allowing for easy day trips while resting in a quieter location. I would definitely stay here again."
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Colorful cottage w/shared pool, central AC, washer/dryer
Pool
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!
A heated pool
PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!
9.8 out of 10, Exceptional, (12)
"Overall great. Loved location. Friendly locals enhanced experience. Only complaint was with mid stay clean that was required. Suggestions for mid clean- Should be different in some ways than final clean - - - - I’d set time on coffee pot so could set up night before and have coffee ready in am. Was unplugged during clean. Making me have to reset time again. Blender/toaster set out on counter to use without having to get down on floor to retrieve them from small cabinet between stove...
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!
Outdoor 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, (2)
"The views and facilities are excellent!! The gutters falling off during a rainstorm were spectacular. The no see-ums were abundant this time of year (spring). We were bitten badly. We didn't realize that no see-um bites would hurt so much and last so long! But overall our stay was fantastic! "
Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Interior
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
3.5 star property
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
Beach
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
9.0 out of 10, Wonderful, (164)
"Lovely home! Fabulous location near the dog beach and restaurants on the beach! Convenient f oh r exploring the island!"
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Beach nearby, beach towels
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
10.0 out of 10, Exceptional, (172)
"Key West is built for small (4-6) family vacations. This property is well-suited to support that. Close to the action means lots of “walkability”. Well appointed with all the needed features. Easy check in, check out. Affordable."
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
Don't see what you're looking for?
See all available properties in Fleming Key
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.

Other property types in Fleming Key

Steps from Duval, Pool & Bikes $129-$299 Night!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (334)
"Listing was accurate. Scuba masks were available and beach chairs which was a great surprise. Room was very clean. Great location and great communication. We will definitely stay again. Thank you!"
The price is £190
includes taxes & fees
25 Jun - 26 Jun
Steps from Duval, Pool & Bikes $129-$299 Night!
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, (100)
"Nice spot away from the crowd but close enough to walk/scoot/bike to. If you plan on parking its first come first serve and not a lot of room for vehicles in the gravel driveway. Maybe 5 cars max if guests know how to park efficiently. If not then youll have to scout the street for a spare spot. I rented a scooter so no issue for finding parking in the driveway. Easy check in and the room( I stayed in the Havana) was small but big enough for one person; two if your spouse packs light and is easy...
The price is £219
includes taxes & fees
21 Jun - 22 Jun
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Aqua Lodges at Hurricane Hole Marina
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (92)
"We received info on how to check in via self-service. Very easy to check in and get our key to the lodge. Lodge itself was clean and adorable. We loved sitting on the deck watching the water and the floating tikis. Would go back for sure"
The price is £207
includes taxes & fees
24 Jun - 25 Jun
Aqua Lodges at Hurricane Hole 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.

Fleming Key Cottages information

Number of reviews
753
Accommodation
56 Cottages
Lowest Price
£312
Highest Price
£312

Frequently asked questions

Why book your cottage in Fleming Key with Expedia?
Reserving a cottage in Fleming Key is as easy as clicking on your travel dates and picking your ideal place for outdoor fun and relaxation. From luxurious retreats to budget-friendly properties and holiday cottages that include perks like a hot tub, Expedia has something for all tastes. As for the best deals around? We’ve have them as well!
How can I find cheap cottages in Fleming Key?
An excellent way to spot cheap cottages in Fleming Key is with Expedia’s user-friendly filter tool. Tailor your search results by amenities, budget and star rating to secure unbeatable prices in just a few clicks.

Fleming Key Hotel Reviews
Expedia verified reviews

Southernmost Beach Resort

Southernmost Beach Resort

5/5 Excellent
"Great location around delicious spots to eat, and the hotels beach restaurant/bar is fantastic!! Clean and friendly "
A verified traveller stayed at Southernmost Beach Resort
Posted 3 days ago
Southernmost Beach Resort