Holiday Homes in Stock Island

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Featured Holiday Homes in Stock Island

Fridge, microwave, oven, stovetop
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
10.0 out of 10, Exceptional, (1)
"We had a great time at Pagitt House. The location is central to everything you’d want to do in Key West. The rooms are comfortable and well appointed. We didn’t use the kitchen much but it was well stocked with whatever you might need."
The price is NZ$2,161
per night
17 May - 18 May
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (189)
"The house location was absolutely amazing. Everything was top notch. I would recommend this house over and over again, the back yard is so tranquil and the layouts of the room worked out well for bigger parties."
The price is NZ$2,585
per night
19 May - 20 May
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Pool
Duval Square in Key West
10.0 out of 10, Exceptional, (12)
"Great location and nice accommodations. Very enjoyable trip. Located right by Duvall Loop free trolly so no reason to pay for the old Town Trolly. Only negative is I don’t like having to wash dishes and put away, having to strip beds and do their laundry. This is my vacation so I could do these things at home. Manager helped 2 old people with our luggage because we thought the elevator was out of order. He even took it up the stairs to our bedroom. So nice and helpful!"
Duval Square in Key West
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Fridge, microwave, oven, stovetop
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
9.6 out of 10, Exceptional, (184)
"We had a wonderful, relaxing time. The pool and lanai was awesome. It's a couple bocks to duval street and within walking distance of downtown. The house was clean but it needs some updating, tiles and carpet. We would go again."
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Property grounds
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
9.8 out of 10, Exceptional, (57)
"We had a very positive stay at Tropical Retreat. The property is in a great location and was very comfortable. It was as presented on the website and the property managers were great to work with."
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
Outdoor dining
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.2 out of 10, Wonderful, (174)
"Great location, 23 miles to Key West. View from deck is breathtaking."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Pool
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
10.0 out of 10, Exceptional, (72)
"This home was wonderful! House had all we needed and was very comfortable. Fully gated yard which was perfect for our dog. It was in such a quiet and peaceful part of town that we sat on the deck and enjoyed the small pool every day. We walked into town each day and we explored all of Old Town from the North end (great marina, restaurants and view) to the South end (great views, restaurants and shopping). Would absolutely recommend this home and would we definitely would rent here next time!"
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is NZ$603
per night
28 May - 29 May
Poolside Cottage #411
Property grounds
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
9.0 out of 10, Wonderful, (214)
"Very enjoyable"
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (89)
"Good place. 3 bed rooms all with Queen size beds. It was perfect for us. We sat on the porch mostly when we were there and played games. Not a long ride to Key West. Overall- we were happy and would stay there again."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (183)
"Very nice"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Outdoor dining
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
9.8 out of 10, Exceptional, (59)
"If you like being right downtown in the middle of shops, restaurants and entertainment this place is for you. We parked our car upon arrival and never used it until check out. This is the perfect house for two or maybe three people. We really had a great time."
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
Beach
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (168)
"We had a awesome family time there, everything is pretty and cute. We fishing behind the house, funny time. Everything was perfect to me and my family. Thank you!"
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
A heated pool
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
10.0 out of 10, Exceptional, (54)
"From the moment we arrived at our Key West retreat, we were enchanted despite the initial hiccup of discovering that two of the bedrooms were situated on the third floor. Yes, the stairs were a bit of a challenge, but what awaited us inside made it all worthwhile. The accommodation was exceptionally cozy, with a delightful small pool that became our little oasis. Cleanliness and comfort were top-notch, and the location could not have been better, placing us right in the heart of Kew West and...
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
Property grounds
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.6 out of 10, Exceptional, (90)
"Condo was clean and orderly and as-advertised. Host was easy to deal with. Would've hoped for more paper products for the price we paid! Overall enjoyed our stay. Pool was lovely."
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Pool
Great Family Vacation Rental.
10.0 out of 10, Exceptional, (3)
"The townhome was nice and is located in a quaint community. The pool area was beautiful. We found that we needed to Uber into Key West since parking is very limited and we were told the bus service is often not on time."
Great Family Vacation Rental.
TV
SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!
10.0 out of 10, Exceptional, (16)
"Everything about this was perfect. Location is great. Having a parking spot right at the rear of unit was a huge plus. Communication with property manager was a breeze (and he even got us in early!) Unit was super clean, updated and well stocked. Having the concierge service was definitely an added plus"
SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!
Property grounds
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, (17)
"Great property, great views on the water."
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Exterior
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (217)
"My daughter and I stayed in Cudjoe Key to be close to Key West. The location was good. The unit had everything we needed both inside and out. We grilled and cooked which was great. The beds were comfortable. Unfortunately, the weather did not cooperate and excursions were cancelled so we spent more time in Key West than we had planned. But the unit had lots of games and the TV had the tennis channel which was very nice. All in all, it was a good time."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
A heated pool
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
9.6 out of 10, Exceptional, (156)
"The house was clean and well stocked with essentials, had lots of character and nicely decorated. The backyard was beautiful with an amazing pool and lots of lounge chairs and outdoor seating. Wonderful stay for our group of 6 adults."
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!
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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.

Other property types in Stock Island

Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (85)
"Aqualodges was a unique, great experience. Really enjoyed the marine life right at our dock. The accommodations were clean and comfortable. Cant wait to come back! "
The price is NZ$527
per night
21 May - 22 May
Aqua Lodges at Hurricane Hole Marina
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (9)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Outdoor dining
52' Power Catamaran Yacht at Luxury Resort Marina
10.0 out of 10, Exceptional, (11)
"We had a great time about Blue Jeans! Louie is an amazing host, as responsive as possible, also took us out for a cruise around Key West, AC works great! Easy Golf kart ride from the marina to down town key west. Pool at the marina was nice as well."
52' Power Catamaran Yacht at Luxury Resort Marina
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.

Stock Island Holiday Homes information

Number of reviews
1,545
Accommodation
577 Holiday Homes
Lowest Price
NZ$603
Highest Price
NZ$2,585

Recent Reviews in Stock Island
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