A beach with palm trees, people relaxing on chairs, and colorful kayaks.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Florida Keys cottages

Two small, single-story buildings with a red and yellow exterior, each with a door and windows, and surrounded by greenery and trees.

1. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,003 reviews)
"Cute little cottage perfect for couples had an amazing stay and will definitely be back to tropical cottages again"
United States
Aaron
$79 nightly
The price is $89
Oct 6 - Oct 7
Total with taxes and fees
Tropical Cottages
A floating houseboat with a covered deck and seating area, docked at a marina.

2. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
$270 nightly
The price is $304
Oct 6 - Oct 7
Total with taxes and fees
Old Wooden Bridge Resort and Marina
A cozy outdoor patio area with a wooden deck, a white table, and a cushioned seating area.

3. OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.4 out of 10, Exceptional, (63 reviews)
"We had such a great time on our visit. The place was exactly like the only photos and we enjoyed the pool, the area and the other visiters. Beautiful Old Town feel!"
United States
Debra S.
$491 nightly
The price is $536
Oct 6 - Oct 7
Total with taxes and fees
OSPREY STUDIO @ The Colony-Sleeps up to 4
A two-story building with balconies, surrounded by lush greenery and palm trees.

4. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (36 reviews)
"The location of jolly rooster was great, and we managed to get parking right outside. Very clean property. Host was very responsive to emails while we were there. Would definitely book again"
United States
Pauline B.
$735 nightly
The price is $816
Oct 25 - Oct 26
Total with taxes and fees
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
A two-story building with balconies, surrounded by lush greenery and palm trees.

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

The Dancing Rooster: 2 Blocks from Duval in Old Town.
Old Town Key West
9.8 out of 10, Exceptional, (151 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
$733 nightly
The price is $814
Oct 20 - Oct 21
Total with taxes and fees
The Dancing Rooster: 2 Blocks from Duval in Old Town.
A residential area with houses, a sidewalk, and a small lawn.

6. Cozy Blue Door Duplex, Central in Cutler Bay

Cozy Blue Door Duplex, Central in Cutler Bay
3.0 star property
Cutler Bay
$294 nightly
The price is $332
Oct 25 - Oct 26
Total with taxes and fees
Cozy Blue Door Duplex, Central in Cutler Bay
A multi-story hotel with a central courtyard, palm trees, and outdoor seating areas.

7. Unique Coral Gables cottage

Unique Coral Gables cottage
Flagami
9.0 out of 10, Wonderful, (28 reviews)
"Shops close by, very quiet neighborhood."
United States
Walter
$194 nightly
The price is $216
Oct 6 - Oct 7
Total with taxes and fees
Unique Coral Gables cottage
Exterior

8. Beautiful Red Cottage for a Relaxing Getaway on a Tropical Fruit Farm near Homestead, Florida

Beautiful Red Cottage for a Relaxing Getaway on a Tropical Fruit Farm near Homestead, Florida
Homestead
$162 nightly
The price is $172
Oct 7 - Oct 8
Total with taxes and fees
Beautiful Red Cottage for a Relaxing Getaway on a Tropical Fruit Farm near Homestead, Florida
An outdoor dining area with tables and chairs, overlooking a body of water with buildings in the background.

9. Private Studio with Free Parking

Private Studio with Free Parking
Little Havana
7.6 out of 10, Good, (11 reviews)
"Great location "
United States
Jeffrey
$125 nightly
The price is $138
Oct 15 - Oct 16
Total with taxes and fees
Private Studio with Free Parking
A house with a white exterior, surrounded by lush greenery and a hammock in the yard.

10. Charming 1 bed Apartment in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN

Charming 1 bed Apartment in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN
Coral Way
9.8 out of 10, Exceptional, (7 reviews)
"Great location and easy check in and checkout. "
United States
Raymond Y.
$137 nightly
The price is $152
Oct 18 - Oct 19
Total with taxes and fees
Charming 1 bed Apartment in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN
A theater with a marquee reading 'TOURER' and a sign for 'Corona' on the right.

11. Walk to Restaurants and Shops + Free parking

Walk to Restaurants and Shops + Free parking
Coral Way
8.0 out of 10, Very good, (5 reviews)
"Everything was absolutely perfect. Exactly what you would want with a VRBO. So quaint, clean just everything, not to mention the location. What is special is is in the residential side of little Havana."
United States
Loren G.
$153 nightly
The price is $170
Oct 11 - Oct 12
Total with taxes and fees
Walk to Restaurants and Shops + Free parking
Room

12. Cozy Cottage on a Tropical Fruit Farm for a Peaceful Escape near Homestead, Florida

Cozy Cottage on a Tropical Fruit Farm for a Peaceful Escape near Homestead, Florida
Homestead
$240 nightly
The price is $240
Oct 6 - Oct 7
Total with taxes and fees
Cozy Cottage on a Tropical Fruit Farm for a Peaceful Escape near Homestead, Florida
Interior

13. La Vie Boheme 2, Cozy, Near Coconut Grove

La Vie Boheme 2, Cozy, Near Coconut Grove
3.0 star property
Coral Way
$326 nightly
The price is $368
Oct 18 - Oct 19
Total with taxes and fees
La Vie Boheme 2, Cozy, Near Coconut Grove
Interior

14. La Vie Boheme, Cozy, Minutues to Coconut Grove

La Vie Boheme, Cozy, Minutues to Coconut Grove
3.0 star property
Coral Way
$343 nightly
The price is $387
Nov 2 - Nov 3
Total with taxes and fees
La Vie Boheme, Cozy, Minutues to Coconut Grove
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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Top Florida Keys Hotel Reviews

Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"Exactly the experience we wanted. Great views, great location, fishing off the dock."
Jean-luc 2-night trip
Posted less than an hour ago
Bayside Inn Key Largo

Find out more about Florida Keys

Florida Keys Cottages information

Number of reviews
611
Accommodation
60 Cottages
Lowest Price
$89
Highest Price
$816

Frequently asked questions

How much do cottages in Florida Keys cost?
Prepare to pay between $89 and $816 per night for cottages in Florida Keys. No matter your budget, an awesome stay is only a click or two away on Expedia. These prices were 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.
How many cottages are there in Florida Keys?
Florida Keys has 60 cottages to choose from. Click on your travel dates, enter your destination and get a head start on planning your dream getaway today.
Are there any family-friendly cottages in Florida Keys?
There are family-friendly cottages in locations around Florida Keys, including Key West. Casa Manana Key West Monthly: 2 Br is one option that'll meet your needs in this vibrant city. It has a 3-star rating and amenities such as an oven and a barbecue grill. Also consider Simonton Court Cottages. With housekeeping services and WiFi, this 3-star cottage in Key West will make you and your travel buddies feel nice and relaxed. Key West has tons of family-friendly attractions when you're ready to see the sights. Smathers Beach and South Beach promise fun for the entire crew.
Why book your cottage in Florida Keys with Expedia?
We think that a vacation should be stress-free, so if you're searching for cottages in Florida Keys at an affordable price, Expedia has got you covered. Keep the budget in check and stay in a cheap option far away from the city rush, or splurge on an upmarket cottage to really pamper your favorite people.
How can I find cheap cottages in Florida Keys?
With Expedia's useful filter tool, getting your hands on cheap cottages in Florida Keys has never been easier. To find stays that'll make your hip pocket happy, refine your search results by star rating, budget and amenities.
What is there to do in Florida Keys near my cottage?
You'll discover countless things to keep you on the go in Florida Keys. If you're visiting Key West, swing by Duval Street, Clarence S. Higgs Memorial Beach Park and Nancy Forrester's Secret Garden. Spending your vacay in Key Largo? Jimmy Johnson's Big Chill, Baker's Cay Resort Beach and Bluefin Rock Harbor Marina are among the best sights in this city.

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