Stock Island Rentals

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208 Houses

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 22 minutes

Price per night from

$517

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$859

Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$859

BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$134

Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$859

Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$859

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$4,016

Responds fast! avg. 2 hours 34 minutes

Price per night from

$124

Responds fast! avg. 2 hours 34 minutes

Price per night from

$181

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$1,179

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$484

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$471

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$496

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$510

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$346

Lobster Lagoon

Stock Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$976

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oas

Stock Island house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Price per night from

$801

Responds fast! avg. 2 hours 34 minutes

Price per night from

$181

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$445

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$1,179

Price per night from

$263

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$563

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 22 minutes

Price per night from

$206

Great rentals within 20 miles that match your search

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!

Price per night from

$435

30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$161

Seaside Condo 2 pools. sunny, quiet, near Old Town

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 48 minutes

Price per night from

$107

Olivia Place

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$345

Beautiful Home Located In Quiet neighborhood

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$340

A Change in Latitudes - TRUMAN ANNEX

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$172

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$754

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$792

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 48 minutes

Price per night from

$603

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.

Price per night from

$488

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 1 hour 45 minutes

Price per night from

$344

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