Search Florida Keys Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 24 - Oct 26
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4
In four months
Jan 30 - Feb 1

Cottages in Florida Keys

Old Wooden Bridge Resort and Marina
Exterior

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (259)
"I love this place!!!"
The price is ￥11,611
￥34,324 total
includes taxes & fees
Oct 12 - Oct 13
Old Wooden Bridge Resort and Marina
Tropical Cottages
Standard Cottage, Ensuite (Cottage 10) | Exterior

Tropical Cottages

3.0 star property
8.6 out of 10, Excellent, (876)
"Wonderful place for a short stay"
The price is ￥11,944
￥13,438 total
includes taxes & fees
Oct 13 - Oct 14
Tropical Cottages
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Terrace/patio

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

9.8 out of 10, Exceptional, (24)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location and very nice room"
The price is ￥12,095
￥45,150 total
includes taxes & fees
Oct 14 - Oct 15
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (51)
"We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!"
The price is ￥24,190
￥52,822 total
includes taxes & fees
Oct 24 - Oct 25
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cottage with Pool and Dockage, just minutes to Key West
Exterior

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (155)
"Good Fishing, Good local eateries. "
The price is ￥22,679
￥47,814 total
includes taxes & fees
Oct 12 - Oct 13
Cottage with Pool and Dockage, just minutes to Key West
Living Life Dockside
Marina

Living Life Dockside

The price is ￥57,150
￥71,853 total
includes taxes & fees
Oct 18 - Oct 19
Living Life Dockside
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz
Property grounds

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

9.8 out of 10, Exceptional, (26)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
The price is ￥57,309
￥109,659 total
includes taxes & fees
Oct 19 - Oct 20
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz
Get your ISLAND STLYE on!
Exterior

Get your ISLAND STLYE on!

2.0 star property
9.6 out of 10, Exceptional, (82)
"We had a wonderful and relaxing time. Getting ready to schedule another trip. "
The price is ￥49,054
￥114,640 total
includes taxes & fees
Oct 17 - Oct 18
Get your ISLAND STLYE on!
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Exterior

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

10.0 out of 10, Exceptional, (7)
The price is ￥43,845
￥83,910 total
includes taxes & fees
Nov 4 - Nov 5
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Exterior

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

10.0 out of 10, Exceptional, (127)
"Great time. Would stay again. "
The price is ￥59,720
￥103,736 total
includes taxes & fees
Nov 4 - Nov 5
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Terrace/patio

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

10.0 out of 10, Exceptional, (23)
"Will stay here again "
The price is ￥12,095
￥45,150 total
includes taxes & fees
Oct 13 - Oct 14
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Terrace/patio

Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

9.8 out of 10, Exceptional, (20)
"Place was a perfect location and was so cute."
The price is ￥12,095
￥46,208 total
includes taxes & fees
Oct 12 - Oct 13
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Terrace/patio

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

9.6 out of 10, Exceptional, (21)
"The location was perfect, close enough to walk to anything we needed to get to. The hosts went above and beyond to be helpful and even picked us up from the airport! The room was great and felt very private."
The price is ￥12,095
￥46,208 total
includes taxes & fees
Oct 12 - Oct 13
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.2 out of 10, Very Good, (47)
"Was such a great stay clean and everything we needed "
The price is ￥22,679
￥50,669 total
includes taxes & fees
Oct 12 - Oct 13
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Exterior

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

10.0 out of 10, Exceptional, (23)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is ￥24,795
￥64,638 total
includes taxes & fees
Oct 27 - Oct 28
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Terrace/patio

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

9.6 out of 10, Exceptional, (27)
"Amazing place and location to everything. Will definitely book this property again."
The price is ￥24,795
￥64,336 total
includes taxes & fees
Oct 26 - Oct 27
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
HIDDEN OASIS 3 blocks from Duval
Exterior

HIDDEN OASIS 3 blocks from Duval

2.5 star property
9.6 out of 10, Exceptional, (94)
"We absolutely loved this place! It was quaint and quiet location. It was beautifully landscaped and I loved the Hidden Oasis unit and would stay there again!"
The price is ￥61,754
￥131,498 total
includes taxes & fees
Oct 27 - Oct 28
HIDDEN OASIS 3 blocks from Duval
Charming 1-bedroom cottage in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN
Exterior

Charming 1-bedroom cottage in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN

The price is ￥10,160
￥23,046 total
includes taxes & fees
Oct 13 - Oct 14
Charming 1-bedroom cottage in lovely Miami with AC, TROPICAL FOOD FOREST GARDEN
Walk to Restaurants and Shops - 5S
Fridge, microwave, coffee/tea maker, paper towels

Walk to Restaurants and Shops - 5S

The price is ￥7,603
￥24,429 total
includes taxes & fees
Nov 11 - Nov 12
Walk to Restaurants and Shops - 5S
Privacy and Comfort close to all - 7G
Iron/ironing board, free WiFi, bed sheets

Privacy and Comfort close to all - 7G

8.0 out of 10, Very Good, (5)
"Great location "
The price is ￥4,513
￥17,520 total
includes taxes & fees
Oct 13 - Oct 14
Privacy and Comfort close to all - 7G
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Florida Keys Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"room were cleaned every morning; we were able to park under the room drinks were pricy "
Terry-John 3-night trip
Posted 2 days ago
Cheeca Lodge & Spa

Find out more about Florida Keys

Florida Keys Cottages information

Number of reviews
Accommodation
 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Florida Keys cost?
Prepare to pay between and 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 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.

Explore a world of travel with Expedia