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Compare 92 Cottages in Key West with updated reviews, rates, and availability.

Southernmost Retreat: 2 Blocks from Duval in Old Town.
10.0 out of 10, Exceptional, 98 reviews
"Walking close to Duval. On street parking can be tough but this block is NOT pay to park! Good to know."
The price is $500
$814 total
includes taxes & fees
Jun 13 - Jun 14
Southernmost Retreat: 2 Blocks from Duval in Old Town.
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, 201 reviews
"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 $217
$512 total
includes taxes & fees
Jun 24 - Jun 25
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Old Town Cottage House in Old Town Key West!
Old Town Cottage House in Old Town Key West!
Save an average of 15% on thousands of hotels when you're signed in
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
10.0 out of 10, Exceptional, 195 reviews
"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!
Conch Republic Consul General's Cottage.-Pool-No Contact Check-In
9.2 out of 10, Wonderful, 67 reviews
"Loved the location. Clean, accommodating property. Would recommend and definitely will be back. Nice that there was a pool to come back to after a fun day out and about."
Conch Republic Consul General's Cottage.-Pool-No Contact Check-In
Conch Republic Consul General's Cottage.-Historic District
9.4 out of 10, Exceptional, 138 reviews
"Our stay was for a week and we had the best time. Walking distance to Duval Street was definitely a plus. The on site pool was wonderful to come back to after a day out in the sun. The property owners, who lived right there, were the best hosts and very hospitable. Highly recommend this property and would definitely revisit."
Conch Republic Consul General's Cottage.-Historic District
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!
10.0 out of 10, Exceptional, 2 reviews
BLUE BIRD ~ Adorable 1 BR, 1 Ba Conch Cottage in Bahama Village!
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
10.0 out of 10, Exceptional, 119 reviews
"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…
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 review
"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
Tranquility by Avantstay Close to Duval St w/ BBQ & Shared Pool
4.5 star property
10.0 out of 10, Exceptional, 3 reviews
"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
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!
9.8 out of 10, Exceptional, 12 reviews
"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!
3.0 star property
10.0 out of 10, Exceptional, 2 reviews
"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!
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
9.0 out of 10, Wonderful, 164 reviews
"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
10.0 out of 10, Exceptional, 169 reviews
"Spacious, close to the beach, restaurants, shops and bars. We’d love to return."
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
New Conch cottage, with heated pool, walking distance to downtown Key West.
8.0 out of 10, Very Good, 1 review
"This semi detached 1BR/1 Bath home is perfectly situated in the best kept secret for long stays in Key West - the White Street Gallery District. White Street is the most amenity rich street in Key West. From it's beautiful pier to the south right up to it's north end, White Street offers just about everything you would ever need. This home is located across from Bayview Park, which hosts numerous events throughout the year. There are basketball courts as well as tennis courts and childrens...
New Conch cottage, with heated pool, walking distance to downtown Key West.
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
3.0 star property
Paradise Place by Avantstay Key West Old Town Condo w/ Shared Pool
Maryann's Place - Large Monthly Studio (New Listing)
9.0 out of 10, Wonderful, 4 reviews
"I drove down with my vehicle for one month in March for a "work"-cation - primarily me, then my father visited the final week. The property is nestled in a quiet, suburban neighborhood, with a relatively short walk to Higgs Beach (south shore) and a longer walk to downtown/Duval Street. The property is clean, well-maintained, and had all essentials (toilet paper, paper towels, sponges, dish soap, salt/pepper, pots/pans, etc.) initially stocked as described. Technically on shared property, you...
Maryann's Place - Large Monthly Studio (New Listing)
Quaint Pool Cottage in Old Town Key West Great value
10.0 out of 10, Exceptional, 4 reviews
"Great little house. Walking distance to pretty much all of old town area. Has a nice pool to relax in. HUGE bathroom. Bedrooms are nice sized. Washer/dryer is a huge plus for long stays. The only thing - wish it was closer to the beach…"
Quaint Pool Cottage in Old Town Key West Great value
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See all available properties in 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.

Other property types in Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very Good, 229 reviews
"Perfect location - not to far of a walk from Duval Street and the action but tucked away just enough to be able to have some peace!"
The price is $261
$316 total
includes taxes & fees
Jun 5 - Jun 6
Hyatt Vacation Club at Sunset Harbor, Key West
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, 331 reviews
"Beautiful studio and great location. Communication with the owner was excellent."
The price is $109
$251 total
includes taxes & fees
Jun 20 - Jun 21
Steps from Duval, Pool & Bikes $129-$299 Night!
Poolside Cottage #411
10.0 out of 10, Exceptional, 17 reviews
"Clean. Everything we needed in a key west stay."
The price is $216
$362 total
includes taxes & fees
Jun 4 - Jun 5
Poolside Cottage #411
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.

Key West Cottages information

Number of reviews
785
Accommodation
92 Cottages
Lowest Price
$217
Highest Price
$500

Frequently asked questions

How much do cottages in Key West cost?
Cottages in Key West range between $217 and $500 per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Key West?
A traveler favorite is Simonton Court Cottages. Make yourself comfortable at this 3.5-star stay which comes with a garden and a nearby beach. Simonton Court Cottages is another recommended option worth shortlisting. Unpack your suitcase at this 3.5-star cottage and you’ll have access to amenities such as free WiFi and pet-friendly facilities. You can choose from multiple cottages in Key West with a total average guest review rating of 9.5.
How many cottages are there in Key West?
Pack your suitcase and pick from 92 cottages in Key West. Dreaming of a place where you can relax and stay in touch with nature? Expedia can help you find the ideal getaway in a few quick clicks.
Are there any family-friendly cottages in Key West?
Many visitors searching for a family-friendly cottage in Key West choose Simonton Court Cottages. With a 3.5-star rating and amenities such as a nearby beach and free WiFi, you’re sure to feel right at home here. Another noteworthy pick for families on vacation is Simonton Court Cottages. Free WiFi and housekeeping services help make this 3.5-star cottage a great base for your Key West trip. Key West boasts loads of family-friendly attractions to visit when the kids are getting restless. Smathers Beach and South Beach promise a fun day out for travelers of all ages.
Why book your cottage in Key West with Expedia?
Reserving a cottage in Key West is as simple as deciding on your travel dates and selecting your ideal place for a vacation in the outdoors. From high-end retreats to budget-friendly properties and cottages that include amenities like a kitchenette, Expedia has something for all tastes. As for the best offers around? We’ve got them as well!
How can I find cheap cottages in Key West?
The easiest way to get cheap cottages in Key West is with Expedia’s filter tool. Refine your search by star rating, amenities and budget to access unbeatable deals in a couple of clicks.
What is there to do in Key West near my cottage?
Key West has enough experiences and sights to keep you occupied for weeks, beginning with Smathers Beach. South Beach, Fort Zachary Taylor Historic State Park and Higgs Beach are other popular attractions. If you’re hanging around a while, Key West Aquarium and Boca Chica Nude Beach will put the finishing touches on your itinerary.

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