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Stock Island Rentals

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264 Results

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264 Houses

A Little Slice Of Paradise

Stock Island house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$72

Bogey's Retreat

Stock Island house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$72

Coral Breeze

Stock Island house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$72

((Fantastic value for last minute discounts for gaps ))

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$516

* Best of the Annex Waterfront with Fantastic Weekly Rates *

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$589

Tradewinds

Stock Island condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$116

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Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$138

* New Ownership, New Look, Ocean Hideaway Winter Savings Book now *

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$390

*Spring Discounts Stay on the Ocean Last minute Specials Book & Save *

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$413

* Last minute Specials Caribbean Conch Key West Condo Save *

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$395

Spa Oasis

Stock Island house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$96

Wind Swept

Stock Island house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$76

Coral Villa

Stock Island house

3 bedrooms / 3 bathrooms / sleeps 6

“Coral Villa” This rental was perfect for my family. It was about 10-15 minutes from Duvall Street and Old Town Key West. The pool was a great place to relax. The only downside was the noise from the road right behind our rental, after the first night though we did not notice the noise anymore.

Price per night from

$106

80' luxury yacht

Stock Island house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$3,953

Salt Ponds Sanctuary - Lovely Condo w/ Private Balcony, Shared Pool/Hot Tub, Nea

Stock Island condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$115

New Listing!!! Cocktails & Dreams - Updated Condo, Walk To Duval St, Waterpark,

Stock Island condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$174

Buena Vista

Stock Island townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

Ocean Breeze - Fantastic Smathers Beach Views, Top Floor Condo With Private Balc

Stock Island condo

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$237

Cottage by the Pool

Stock Island townhouse

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$72

Ella Varela - Beautiful Dog Friendly Conch Cottage Conveniently Located in the H

Stock Island house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$174

Bye Bye Birdie

Stock Island townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$96

Coconut Mallory #411, Key West Convenience + Resort Amenities, Pools, Hot Tub, D

Stock Island condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$174

Coconut Mallory #412, Resort Amenities, Pools, Hot Tub, Dockage, Pub and Key Wes

Stock Island condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$174

Lotus Blossom - Updated 3 BR Home With Tropical Courtyard & Hot Tub, Convenient

Stock Island house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$93

Margaretaville - Live Like A Key West Local, Dog Friendly Old Town Home With Pri

Stock Island house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$243

Great rentals within 20 miles that match your search

Old Town Eyebrow:Luxurious/Private Home

Key West house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$555

A LITTLE PIECE OF THE CARIBBEAN IN THE U. S.

Key West condo

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$343

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$322

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$383

Old Town Treasure, Historic Seaport, Conch House 3 Bedrooms 3.5 Baths, Pool

Key West house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$466

Term Charterboat w/ FREE Sunset Cruise

Key West houseboat

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$387

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$582

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$542

Old Town, 5 Bdrm Home with Private Pool in Gated Backyard

Key West house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 18 minutes

Price per night from

$359

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.

Price per night from

$298

Dolphin Bay

Sugarloaf house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$165

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$276

Venture Out 128

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$221

Viewing 38 of 264
rentals in Stock Island

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Top Destination reviews

Wind Swept
Another Great January

Loved " Wind Swept" for its freshness, cleanliness, and cheery feeling. A little tight, but we got used to it. At Home Key West, especially Gail and Bridgette, couldn't have been more helpful and accommodating. A few "extras" we needed were quickly and graciously provided. Location was great. When parking was tight, the pool lot was right there. When my wife needed the car, it was an easy walk to the golf course. The serenity of the backyard "Zen Garden" made sitting on the deck and reading even more pleasurable. Obviously a good find as we are renting again next January.see more
Coral Villa
We loved it.

We were 3 couples who totally enjoyed our stay at coral villas. The only drawback was we love to sit outside on the deck and enjoy our morning coffee or later in the day wine. It was quite noisy because of the traffic. We had to move to the other inside deck which was a lot smaller but much quieter … see more

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