Compare Florida Keys Cottage Rentals

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

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Florida Keys Cottages

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive Big Pine Key FL
$274 nightly
The price is $308 total per night
$308 total
Jan 10 - Jan 11, 2026
Total with taxes and fees
Guests staying at Old Wooden Bridge Resort and Marina enjoy access to a marina, an outdoor pool, and free WiFi in public areas. If you plan to drive, free parking is available. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. Additional amenities include express check-in, a terrace, and barbecue grills.
Pool
Pet friendly
Tropical Cottages

Tropical Cottages

3 out of 5
243 61st Street Gulf Marathon FL
$135 nightly
The price is $152 total per night
$152 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
Tropical Cottages offers a picnic area, barbecue grills, and a garden. If you drive, put free parking to good use. Multilingual staff is on hand to answer questions.
Parking included
Restaurant
Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,

Little Torch Key FL
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

Cudjoe Key FL
$312 nightly
The price is $346 total per night
$346 total
Dec 20 - Dec 21
Total with taxes and fees
At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

Cudjoe Key FL
$315 nightly
The price is $349 total per night
$349 total
Dec 27 - Dec 28
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key FL
$359 nightly
The price is $398 total per night
$398 total
Dec 20 - Dec 21
Total with taxes and fees
Guests of this cottage enjoy features like an outdoor pool, a hot tub, and laundry facilities. This smoke-free cottage also has barbecue grills.
Pool
Hot Tub
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

Cudjoe Key FL
$312 nightly
The price is $346 total per night
$346 total
Dec 20 - Dec 21
Total with taxes and fees
At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills.
Pool
Kitchen
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key FL
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!

Cudjoe Key FL
$286 nightly
The price is $317 total per night
$317 total
Dec 20 - Dec 21
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Florida Keys
View all properties
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.

Florida Keys Beach Accommodation

    Southernmost Beach Resort and Guesthouses

    Southernmost Beach Resort and Guesthouses

    1319 Duval Street Key West FL
    $345 nightly
    The price is $389 total per night from Jan 13 to Jan 14
    $389 total
    Jan 13 - Jan 14, 2026
    Total with taxes and fees
    8.6/10 Excellent! (2,924 reviews)
    Ocean Key Resort - A Noble House Resort

    Ocean Key Resort - A Noble House Resort

    Zero Duval St. Key West FL
    $614 nightly
    The price is $691 total per night from Jan 5 to Jan 6
    $691 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    9/10 Wonderful! (1,001 reviews)
    Hampton Inn Key West FL

    Hampton Inn Key West FL

    3755 S Roosevelt Blvd Key West FL
    $278 nightly
    The price is $313 total per night from Jan 4 to Jan 5
    $313 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9/10 Wonderful! (1,289 reviews)
    Blue Flamingo Resort Key West

    Blue Flamingo Resort Key West

    3820 North Roosevelt Boulevard Key West FL
    $276 nightly
    The price is $310 total per night from Jan 19 to Jan 20
    $310 total
    Jan 19 - Jan 20, 2026
    Total with taxes and fees
    8/10 Very Good! (1,763 reviews)
    Baker's Cay Resort Key Largo, Curio Collection by Hilton

    Baker's Cay Resort Key Largo, Curio Collection by Hilton

    97000 Overseas Hwy Key Largo FL
    $450 nightly
    The price is $506 total per night from Jan 5 to Jan 6
    $506 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.6/10 Excellent! (1,005 reviews)
    Oceans Edge Key West Resort, Hotel & Marina

    Oceans Edge Key West Resort, Hotel & Marina

    5950 Peninsular Avenue Key West FL
    $277 nightly
    The price is $311 total per night from Jan 8 to Jan 9
    $311 total
    Jan 8 - Jan 9, 2026
    Total with taxes and fees
    8.8/10 Excellent! (1,751 reviews)
    Islander Resort

    Islander Resort

    82100 Overseas Highway Islamorada FL
    $329 nightly
    The price is $371 total per night from Jan 4 to Jan 5
    $371 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (1,006 reviews)
    The Reach Key West, Curio Collection by Hilton

    The Reach Key West, Curio Collection by Hilton

    1435 Simonton Street Key West FL
    $383 nightly
    The price is $430 total per night from Jan 13 to Jan 14
    $430 total
    Jan 13 - Jan 14, 2026
    Total with taxes and fees
    8.4/10 Very Good! (1,002 reviews)
    Ocean Pointe Suites at Key Largo

    Ocean Pointe Suites at Key Largo

    500 Burton Dr Tavernier FL
    $193 nightly
    The price is $215 total per night from Jan 13 to Jan 14
    $215 total
    Jan 13 - Jan 14, 2026
    Total with taxes and fees
    8.2/10 Very Good! (1,003 reviews)

Hotel Options in Florida Keys

    Reefhouse Resort & Marina

    Reefhouse Resort & Marina

    103800 Overseas Hwy Key Largo FL
    $269 nightly
    The price is $298 total per night from Dec 21 to Dec 22
    $298 total
    Dec 21 - Dec 22
    Total with taxes and fees
    9.2/10 Wonderful! (1,334 reviews)
    Isla Bella Beach Resort & Spa

    Isla Bella Beach Resort & Spa

    1 Knights Key Boulevard Marathon FL
    $407 nightly
    The price is $458 total per night from Jan 6 to Jan 7
    $458 total
    Jan 6 - Jan 7, 2026
    Total with taxes and fees
    9/10 Wonderful! (1,069 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy Islamorada FL
    $213 nightly
    The price is $240 total per night from Jan 14 to Jan 15
    $240 total
    Jan 14 - Jan 15, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (1,598 reviews)

Cottages

Book a cottage in Florida Keys
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Florida Keys. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Florida Keys better.

Cottage apartments in Florida Keys range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Florida Keys
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Florida Keys and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Florida Keys cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Florida Keys. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Florida Keys Cottages essential information

Accommodation
64 Cottages
Lowest Price
$152
Highest Price
$691
Popular accommodation
Old Wooden Bridge Resort and Marina, Tropical Cottages, Direct Oceanfront Cottage-Sunrise View- #2,, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Cottage with swimming pool and dockage, just minutes to Key West!, Canal front, dockage, 2 bedroom, 2 bath, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Cottage with Pool and Boat Dockage just minutes to Key West!, Quaint cottage, pool, dockage just minutes to Key West!