Compare Key West Cottage Rentals

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Featured Key West Cottages

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

At this cottage, guests have access to barbecue grills.
SEPTEMBER SPECIAL-Downtown Location in Historic District-No Contact Check-In

SEPTEMBER SPECIAL-Downtown Location in Historic District-No Contact Check-In

At this cottage, guests have access to an outdoor pool and barbecue grills.
Sea Breeze Cottage in Truman Annex Location! Location! Location!

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

Guests staying at this cottage enjoy features like a water park, an outdoor pool, and a garden.
Southernmost Retreat: 2 Blocks from Duval in Old Town.

Southernmost Retreat: 2 Blocks from Duval in Old Town.

This cottage is a smoke-free cottage.
Downtown Cottage just off famous Duval Street-No Contact Check-In

Downtown Cottage just off famous Duval Street-No Contact Check-In

Guests staying at this cottage have access to a garden and barbecue grills.
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!

3.5 out of 5
1075-29 Duval Square, Key West, FL
An outdoor pool and free WiFi in public areas are features at this cottage. If you decide to drive, there's free parking. Helpful staff is there to provide concierge services, as well as offer insight about the area.
Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays

3 out of 5
An outdoor pool and free WiFi in public areas are features at this cottage. If you drive, take advantage of free parking.
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!

~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!

Guests staying at this cottage have access to barbecue grills and a garden.
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…

**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…

Guests staying at this cottage enjoy free WiFi in public areas, a spa tub, and barbecue grills. There's free offsite parking if you drive. Staff members can help with accommodation requests, and provide concierge services.
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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 Beach Accommodation

    Southernmost Beach Resort

    Southernmost Beach Resort

    1319 Duval Street, Key West, FL
    The price is $269 per night from Oct 1 to Oct 2
    $269
    per night
    Oct 1 - Oct 2
    8/10 Very Good! (1,709 reviews)
    Ocean Key Resort - A Noble House Resort

    Ocean Key Resort - A Noble House Resort

    Zero Duval St., Key West, FL
    The price is $368 per night from Oct 16 to Oct 17
    $368
    per night
    Oct 16 - Oct 17
    9.2/10 Wonderful! (1,000 reviews)
    Hampton Inn Key West FL

    Hampton Inn Key West FL

    3755 S Roosevelt Blvd, Key West, FL
    The price is $159 per night from Oct 2 to Oct 3
    $159
    per night
    Oct 2 - Oct 3
    8.8/10 Excellent! (1,145 reviews)
    24 North Hotel Key West

    24 North Hotel Key West

    3820 North Roosevelt Boulevard, Key West, FL
    The price is $134 per night from Oct 1 to Oct 2
    $134
    per night
    Oct 1 - Oct 2
    7/10 Good! (1,445 reviews)
    Oceans Edge Key West Resort, Hotel & Marina

    Oceans Edge Key West Resort, Hotel & Marina

    5950 Peninsular Avenue, Key West, FL
    The price is $169 per night from Oct 11 to Oct 12
    $169
    per night
    Oct 11 - Oct 12
    8.8/10 Excellent! (1,650 reviews)
    The Reach Key West, Curio Collection by Hilton

    The Reach Key West, Curio Collection by Hilton

    1435 Simonton Street, Key West, FL
    The price is $264 per night from Oct 18 to Oct 19
    $264
    per night
    Oct 18 - Oct 19
    8.2/10 Very Good! (482 reviews)
    The Mansion on the Sea - Southernmost House in the USA

    The Mansion on the Sea - Southernmost House in the USA

    1400 Duval Street, Key West, FL
    The price is $375 per night from Oct 1 to Oct 2
    $375
    per night
    Oct 1 - Oct 2
    9.2/10 Wonderful! (998 reviews)
    Pier House Resort & Spa

    Pier House Resort & Spa

    1 Duval St, Key West, FL
    The price is $323 per night from Oct 2 to Oct 3
    $323
    per night
    Oct 2 - Oct 3
    8.8/10 Excellent! (1,000 reviews)
    Hyatt Centric Key West Resort and Spa

    Hyatt Centric Key West Resort and Spa

    601 Front St, Key West, FL
    The price is $288 per night from Oct 2 to Oct 3
    $288
    per night
    Oct 2 - Oct 3
    8.8/10 Excellent! (1,000 reviews)

Hotel Options in Key West

    Southernmost Beach Resort

    Southernmost Beach Resort

    1319 Duval Street, Key West, FL
    The price is $269 per night from Oct 1 to Oct 2
    $269
    per night
    Oct 1 - Oct 2
    8/10 Very Good! (1,709 reviews)
    Oceans Edge Key West Resort, Hotel & Marina

    Oceans Edge Key West Resort, Hotel & Marina

    5950 Peninsular Avenue, Key West, FL
    The price is $169 per night from Oct 11 to Oct 12
    $169
    per night
    Oct 11 - Oct 12
    8.8/10 Excellent! (1,650 reviews)
    Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    2001 South Roosevelt Boulevard, Key West, FL
    The price is $212 per night from Oct 30 to Oct 31
    $212
    per night
    Oct 30 - Oct 31
    8.6/10 Excellent! (1,871 reviews)

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.

Key West Cottages essential information

Accommodation
85 Cottages
Lowest Price
$134
Highest Price
$375
Popular accommodation
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK, SEPTEMBER SPECIAL-Downtown Location in Historic District-No Contact Check-In, Sea Breeze Cottage in Truman Annex Location! Location! Location!, Southernmost Retreat: 2 Blocks from Duval in Old Town., Downtown Cottage just off famous Duval Street-No Contact Check-In, Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!, Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays, ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!, **DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…

Cottages in Key West

Most Popular

More Places To Stay in Key West