Cottages Key West

Updating...

age 0-16
96 Results

Relevance

Price: low to high

Price: high to low

Reviews

96 cottages

Historic Carriage House

Key West cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

Match: Rental types Microwave

All filters match

Price per night from

$230

These homes match some but not all of your filters. Clear all filters

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$179

Southernmost Beauty

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$268

One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$339

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$859

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 46 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$384

New Listing Family Friendly

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$367

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$153

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$138

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$93

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$180

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$115

Key West Suites Hotel unit 201

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$1,145

American Shoal Lighthouse Suite Duval St. and Pool

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$430

Clean Apartment in Old Town Key West (Best Downtown Locations)

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 46 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$384

The Tree House Old Town 2 Bedroom MONTHLY Rental

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$134

Nature's Boutique

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$230

"Little Paradise" Historic Seaport Old Town Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$492

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$344

BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$382

Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$840

Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$478

Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$458

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$344

Studio Blue

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$331

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 2 hours 41 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$321

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$201

Shipyard-1/2 Block Duval Street

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$229

The Mermaids House, Historic Old Town Key West

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$328

Harbor Walk Hideaways

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$1,302

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$488

Conch Haven Cottage Old Town Studio MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$108

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$435

Henry's Piece Of Paradise On The Ocean In Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“nice place” Accommodations were nice Good view Henry was great to work with

1 of 2 match: Rental types, Microwave

1 of 2 filters match

Price per night from

$465

Viewing 38 of 96
rentals in Key West

×

Also consider