Holiday Homes in Stock Island

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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

Featured Holiday Homes in Stock Island and around

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

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

9.0 out of 10, Wonderful, (34)
"Great place in a very convenient location! Pull out couch isn’t the most comfortable thing in the world, but it sleeps. Super clean, super easy check in (was even able to get in early) and a great price! "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Spec.Feb.24-Mar 1 @275 lodg + w. 3 night stay close beach
Terrace/patio

Spec.Feb.24-Mar 1 @275 lodg + w. 3 night stay close beach

9.0 out of 10, Wonderful, (157)
"The good: convenient location, quiet, bed was comfortable, the little patio in the back is nice. The bad: there is no “on site’ parking but we always found parking on the street about a block away, The communication with property manager was a bit strange, she accused us of still being inside the unit a full day after we had check out on time, despite texting her to tell her we had left (an hour before check out)"
Spec.Feb.24-Mar 1 @275 lodg + w. 3 night stay close beach
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is €515
includes taxes & fees
12 Feb - 13 Feb
Poolside Cottage #411
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Property grounds

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

9.6 out of 10, Exceptional, (31)
"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!
Feb 3-10 $245 off the rates close beach full kitchen & patio
Exterior detail

Feb 3-10 $245 off the rates close beach full kitchen & patio

9.6 out of 10, Exceptional, (208)
"We always stay at this location when available. There’s another one at the rear of the property and it was a good spot but we’re spoiled by this one. We’ve stayed here so much it is almost like a second home. It’s well appointed, the shower is huge and the place is cozy and has the lived in feel to it. There’s plenty of basics in the kitchen, full size fridge and stove, the bed is outstanding and adjustable, and there’s even beach chairs to use while staying. Marilyn is a great host and super...
Feb 3-10 $245 off the rates close beach full kitchen & patio
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
A heated pool

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
A heated pool

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!
Property grounds

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!
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
A heated pool

Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location

10.0 out of 10, Exceptional, (3)
"Had a wonderful short trip to the keys - this place was in the perfect location to walk all of Key West from shopping Duval street shopping and sight seeing ate lighthouse and even the coast guard station - would highly recommend. "
The price is €850
includes taxes & fees
11 Feb - 12 Feb
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
A heated pool

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

9.8 out of 10, Exceptional, (90)
"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!
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Terrace/patio

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

9.6 out of 10, Exceptional, (25)
"Great property! Easy to get back and forth to Key West! Loved the water view!"
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
3 night minimum! Spectacular Ocean Views!
A heated pool

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
Exterior

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
The Flower Power House - Boho Beautiful
A heated pool

The Flower Power House - Boho Beautiful

2.5 star property
8.8 out of 10, Excellent, (25)
"We truly enjoyed our stay at the Flower Power House! The house was awesome, in a great neighborhood and had everything we needed! The property manager was very pleasant, responsive and accommodating! We will definitely return the next time we are in Key West! Thank you! "
The Flower Power House - Boho Beautiful
Conch Cove - 3br/3ba with private heated pool and private parking
A heated pool

Conch Cove - 3br/3ba with private heated pool and private parking

10.0 out of 10, Exceptional, (4)
"Rick and team were awesome and exceptional throughout the whole stay! Nice house!! "
The price is €1,713
includes taxes & fees
13 Feb - 14 Feb
Conch Cove - 3br/3ba with private heated pool and private parking
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
Miscellaneous

Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!

2.0 star property
6.0 out of 10, (2)
"Plenty of room indoors and outdoors to live in. Comfortable beds. Clean and tidy"
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining

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

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

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

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

10.0 out of 10, Exceptional, (214)
"Great location and a clean home. "
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
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
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (114)
"Great getaway, yet very close to Key West. It is about a 5-10 minute drive from property to Duval Street."
The price is €320
includes taxes & fees
9 Feb - 10 Feb
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!
Property grounds

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.