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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 709 Vacation Homes in Stock Island with updated reviews, rates, and availability.

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Grill up your fresh catch (Kayaks not included)

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (33)
"It was just the right place for my family. We really enjoyed the view and close proximity to Key West. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Spec. Jan 26-31 --219. lodg + w. 3 night stay close beach
Dining Area

Spec. Jan 26-31 --219. lodg + w. 3 night stay close beach

9.0 out of 10, Wonderful, (156)
"Excellent location very clean. Excellent communication with the owner of the accommodations were wonderful. We enjoyed our New Year’s."
Spec. Jan 26-31 --219. lodg + w. 3 night stay close beach
Poolside Cottage #411
Pool

Poolside Cottage #411

10.0 out of 10, Exceptional, (37)
"From the moment we stepped on the property it was a great experience. We were pleasantly surprised to have a small water view from the front deck of the condo. Walking/biking trail was accessible right outside the property and we could easily walk to a public beach from the property. The condo was well stocked and we had everything we needed to cook our own meals. The resort was quiet and extremely clean. Only disappointment was that “Gumbos” the small bar on property has been closed. Will...
The price is AED 893
AED 1,483 total
includes taxes & fees
28 Jan - 29 Jan
Poolside Cottage #411
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Sunny days ahead

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

9.6 out of 10, Exceptional, (30)
"This was a very smooth, perfect 5 night visit. The property offered us everything that we could need. It was a short drive to Duval St and all of the activities in Key West yet the property was very peaceful with a wonderful waterfront patio that we sat out on and enjoyed. The hot tub was a nice treat as well. I have to mention the incredible responsiveness of the property manager. Every question that I had they responded to within minutes which was very much appreciated. "
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Winter spec 279.lodg. + extras Close to beach w full kitchen. & patio
Varela St. downstairs front porch

Winter spec 279.lodg. + extras Close to beach w full kitchen. & patio

9.6 out of 10, Exceptional, (208)
"The location, size and layout were excellent. For the cost, however, it was lacking in cleanliness, and shabby, bleach-stained bath towels, and as others have mentioned, the lack of shampoo, soap, a dish towel and dish drainer, are unacceptable. "
Winter spec 279.lodg. + extras Close to beach w full kitchen. & patio
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Private home with Old Town Charm

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

9.6 out of 10, Exceptional, (175)
"My family enjoyed our stay at Captain’s Quarters. The children especially enjoyed the heated pool and there was adequate room for the seven of us. The bedding was comfortable and it was handy that all of the bedrooms had TVs. There is normally places to park out front if one happens to have a golf cart. There are some issues that need to be addressed and we had many electrical plugs that were very old and wouldn’t work so charging phones became an issue. … It could use a freshen up as window...
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
Villa Déjà vu Key West - Steps Off Duval w Private Pool
living room

Villa Déjà vu Key West - Steps Off Duval w Private Pool

9.4 out of 10, Exceptional, (54)
"Amazing time and experience! "
Villa Déjà vu Key West - Steps Off Duval w Private Pool
Coastal Comfort; Waterfront Luxury Home with private pool!

Coastal Comfort; Waterfront Luxury Home with private pool!

9.4 out of 10, Exceptional, (63)
"This property was awsome! The area is quiet and close to grocery stores. And a.short drive to down townlpve it, love it, love it. Definitely coming back!!"
Coastal Comfort; Waterfront Luxury Home with private pool!
3 night minimum! Spectacular Ocean Views!
Exterior

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very Good, (18)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Front / Side View of home

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (234)
"Clean, easy access, friendly complex/neighborhood. "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
Welcome to the HEART of DUVAL!

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (88)
"Beautiful property. Great communication. Very clean. Literally right next to duval street. Highly recommend "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Welcome to Mango Margarita!

MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

9.6 out of 10, Exceptional, (200)
"Delighted with the location & size. Quiet but close to activities. Enjoyed the outdoor space- well appointed."
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Plush linen

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

9.6 out of 10, Exceptional, (24)
"This property was clean and easy to find. Had to reach out to get access to the property well past the check in time. Minimal kitchen supplies but sufficient. "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Entrance of the heated pool overlooking Cudjoe Bay.

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

10.0 out of 10, Exceptional, (212)
"We had a really nice relaxing week! Easy drive into Key West or up the keys for excursions. Comfortable and peaceful. We had everything we needed."
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
Welcome to island time!

BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!

9.6 out of 10, Exceptional, (65)
"Overall the best things about the home was location to Duval St and historic sites. The pool was relaxing and the large covered porch with big table was an ideal place to eat and hang outdoors."
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w/ Private Pool!
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Cozy decor

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.4 out of 10, Exceptional, (29)
"Excellent views, very quiet, pool was outstanding "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Gone Coastal
Pool

Gone Coastal

9.8 out of 10, Exceptional, (9)
"Love the stay everything was amazing "
The price is AED 951
AED 2,055 total
includes taxes & fees
24 Feb - 25 Feb
Gone Coastal
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
Natural lighting

BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!

9.8 out of 10, Exceptional, (63)
"Except for the very uncomfortable couch we had a nice stay."
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Relax on the little sandy beach.

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (221)
"Everything was very nice. We enjoyed sitting down by the water any time. It was close to everything we were interested in seeing and doing. Great stay."
The price is AED 1,561
AED 3,329 total
includes taxes & fees
20 Feb - 21 Feb
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Pool

Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!

9.8 out of 10, Exceptional, (217)
"The William Skelton house is a terrific property. We had a bunch of couples and the house was perfectly located from the fun on Duval street, the marina area and some great restaurants and bars a few minutes away from the stuff of Duval. The property owners were great with answering questions and this property is highly recommended. "
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
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.
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Other property types in Stock Island

Aqua Lodges at Hurricane Hole Marina
Exterior

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (114)
"This was a terrific quick visit, will be back next year for a longer stay. Boat was clean, deck was nice to sit and have a meal or watch the water and the activities. Recommend highly!"
The price is AED 479
AED 1,056 total
includes taxes & fees
28 Jan - 29 Jan
Aqua Lodges at Hurricane Hole Marina
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Miscellaneous

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

10.0 out of 10, Exceptional, (2)
"Owner communication was great and Master Suite was very comfortable. AC worked great, boat has lot of bathroom space! Our charter to see the sunset was spectacular with such a great kind crew that did a professional job. Our stay overall was verand will book again on our next trip"
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Beach

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

9.8 out of 10, Exceptional, (17)
"Rented this nice boat for 2 nights for a two 60-somethings and three 20-somethings. From "A to Z" it meet or exceeded our expectations. Boat was a bit old, the carpets, etc. were more that a bit "dingy", and 5 adults certainly "maxed out" the space.... but we didn't care much. It was such a unique experience for our 3 younger guests who had NEVER been on a boat before. The harbor is very nice with good restaurants. etc. Jim our "check-in /out" guy was great. Jeff our captain for our 4 hour boat...
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
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.