Key West, FL Cottages: $116 Key West Cottage Rentals

Featured Key West Cottages

Price for 1 night 2 adults*

Simonton Court Cottages

3.5 out of 5.0 910 Simonton, Key West, FL

$165

Per night/room

Jun 15 - Jun 16

Simonton Court Cottages features free WiFi in public areas and a garden. Helpful staff is there to provide front-desk service during limited hours, as well as ...

~ Solaris Garden ~ Enjoy Old Town Livin' Just A Short Walk to All the Action!

Key West, FL

At this cottage, guests have access to a garden.

Colony Calypso - A Quaint 1 Bedroom Cottage Just two Blocks to Duval

Key West, FL

This cottage is a smoke-free cottage.

Colony Sunset- Bright and Airy Cottage in the Heart of old Town Key West

Key West, FL

This cottage is a smoke-free cottage.

Colony Poolside: A Charming Bungalow Near the Historic Cemetery

Key West, FL

This cottage is a smoke-free cottage.

Pete's West Cottage Steps From Duval

Key West, FL

This cottage is a smoke-free cottage.

~ Chick-a-pea Cottage ~ Breathtaking Home w/ Pool & Parking, 1 Block to Duval

Key West, FL

This cottage features an outdoor tennis court and a garden.

Sea Breeze Cottage in Truman Annex Location! Location! Location!

Key West, FL

This cottage features a water park and a garden.

Simonton Court Cottages

3.5 out of 5.0 910 Simonton Street, Key West, FL

At Simonton Court Cottages, guests have access to free WiFi in public areas. Transportation is made easy with a free area shuttle. Helpful staff is there to ...

See all 806 Properties in Key West

Key West Beach Accommodation

Price for 1 night 2 adults*

Southernmost House

3.0 out of 5.0 1400 Duval Street, Key West, FL

$274

Per night/room

Jun 17 - Jun 18

4.9/5 (17 reviews)

The house was built in 1897 and has vast amount of rich history; from being the mansion of Florida's first millionaire, to a speakeasy where All Capone was almost asassinated, to a favorite vacation spot for many US presidents. Besides the history, it is very relaxing here. The pool is very clean ...

Reviewed on Oct 11, 2019

Guests of Southernmost House enjoy features like an outdoor pool, free WiFi in public areas, and free newspapers. Self parking is available for USD 20 per night. ...

Ocean Key Resort - A Noble House Resort

4.0 out of 5.0 Zero Duval St., Key West, FL

$349

Per night/room

Jul 1 - Jul 2

4.5/5 (197 reviews)

Great location. Beautiful property and friendly staff.

Reviewed on Feb 28, 2020

Guests staying at Ocean Key Resort - A Noble House Resort enjoy access to a full-service spa, an outdoor pool, and free WiFi in public areas. Valet parking is ...

Pier House Resort & Spa

4.0 out of 5.0 1 Duval St, Key West, FL

$238

Per night/room

Jun 21 - Jun 22

4.4/5 (181 reviews)

Everything was awesome Most of all the friendliness of the staff

Reviewed on Feb 23, 2020

Guests of Pier House Resort & Spa have access to a private beach, a full-service spa, and an outdoor pool. The front desk has multilingual staff on hand 24/7 ...

Oceans Edge Key West Resort, Hotel & Marina

4.0 out of 5.0 5950 Peninsular Avenue, Key West, FL

$143

Per night/room

Jun 7 - Jun 8

4.4/5 (105 reviews)

Good amd friendly service. They were welcoming also

Reviewed on Jan 20, 2020

Guests of Oceans Edge Key West Resort, Hotel & Marina have access to a marina, 6 outdoor pools, and a 24-hour fitness center. If you drive, self parking is USD ...

Hyatt Centric Key West Resort and Spa

4.0 out of 5.0 601 Front St, Key West, FL

$309

Per night/room

Jun 25 - Jun 26

4.3/5 (152 reviews)

Wonderful! Great location. Enjoyed walking everywhere.

Reviewed on Jan 26, 2020

At Hyatt Centric Key West Resort and Spa, guests enjoy a marina, an outdoor pool, and a 24-hour fitness center. Valet parking is available for USD 27 per night. ...

Southernmost Beach Resort

4.0 out of 5.0 1319 Duval Street, Key West, FL

$287

Per night/room

Jun 8 - Jun 9

4.3/5 (190 reviews)

The property is huge. The grounds are well kept. Plenty of chairs available at the pools. Employees polite and helpful. Room was comfortable. The Tranquility Pool needed some love. Lounge chairs comfortable, but needed cleaning. The area needed to be maintained btter - swept, hosed down.

Reviewed on Feb 22, 2020

Guests of Southernmost Beach Resort have access to a full-service spa, 3 outdoor pools, and a fitness center. Self parking is offered for USD 31.50 per day. ...

Hampton Inn Key West FL

2.5 out of 5.0 3755 S Roosevelt Blvd, Key West, FL

$149

Per night/room

Jun 7 - Jun 8

4.1/5 (86 reviews)

Very close to the airport and shuttle service to the town.

Reviewed on Mar 7, 2020

Built in 2019, the brand new Hampton Inn Key West FL offers an outdoor pool, a 24-hour fitness center, and free WiFi in public areas. There's free parking, as ...

24 North Hotel Key West

4.0 out of 5.0 3820 North Roosevelt Boulevard, Key West, FL

$116

Per night/room

Jun 14 - Jun 15

4.0/5 (91 reviews)

No breakfast. 😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😎😎😎😎😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭😭

Reviewed on Jan 23, 2020

Built in 2015, the brand new 24 North Hotel Key West features a marina, an outdoor pool, and a fitness center. There's free parking and an area shuttle. Front-desk ...

The Reach Key West, Curio Collection by Hilton

3.5 out of 5.0 1435 SIMONTON STREET,1435, Key West, FL

$285

Per night/room

Jun 11 - Jun 12

Guests of The Reach Key West, Curio Collection by Hilton have access to a private beach, a full-service spa, and an outdoor pool. Valet parking is available ...

See all 806 Properties in Key West

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Cottages

Book a cottage in Key West
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Key West. 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 Key West better.

Cottage apartments in Key West 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 Key West
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 Key West 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 Key West 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 Key West. 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.