Stock Island Rentals

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187 Houses

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 6 minutes

Price per night from

$687

Key West Retreat Private Nature preserve neat the ocean

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 40 minutes

Price per night from

$859

Caribbean Conch your Key West Oasis awaits. Great Summer specials

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 40 minutes

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

Responds fast! avg. 3 hours 40 minutes

Price per night from

$134

Spring Discounts Stay on the Ocean Last minute Specials Book and Save

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 40 minutes

Price per night from

$859

Steps to the Ocean's Edge & a short bike ride downtown. Best value at 1800

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 40 minutes

Price per night from

$859

Ananda - Walk To Smathers Beach, Shared Pool/Spa & Dog Friendly!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$179

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$4,008

Poseidons Paradise - Luxurious Waterfront Home in Key West, Amazing Backyard Oas

Stock Island house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$179

Price per night from

$124

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

$800

Price per night from

$180

Price per night from

$172

Price per night from

$179

Price per night from

$180

Cottage On Newton - Quiet Meadows Location, Close To Duval St, Historic Seaport

Stock Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$179

Price per night from

$86

Price per night from

$179

Price per night from

$180

Atreo - Unique & Updated Canal Home On Big Coppitt Key, Interior Courtyard, Dock

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$180

Windsor Mansion - Amazing Old Town Key West Complex, Pool/Spa, Room For Your Fam

Stock Island house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 16

Price per night from

$180

Price per night from

$180

Paradise - Beautifully Updated Conch Home, Pool, Quiet But Close Enough To Walk

Stock Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$179

Great rentals within 20 miles that match your search

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.

Price per night from

$315

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

Price per night from

$573

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.

Responds fast! avg. 1 hour 14 minutes

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!

Price per night from

$1,300

Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE

Key West apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

Price per night from

$315

“Wonderful Experience” Beautiful decor! Perfect location - just off the beaten path but out of the hustle and bustle. Convenient to everything we wanted to do! I whole heartedly recommend this condo for a couple. Also would work nicely for three people. Might be a bit tight for four adults, but it was perfect for my husband and me.

Responds fast! avg. 1 hour 47 minutes

Price per night from

$296

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$773

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$790

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. 2 hours 45 minutes

Price per night from

$602

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.

Responds fast! avg. 1 hour 37 minutes

Price per night from

$498

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 55 minutes

Price per night from

$343

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$130

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!!!!

Price per night from

$140

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$130

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!

Responds fast! avg. 3 hours 59 minutes

Price per night from

$434

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