Holiday Homes in Stock Island

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Featured Holiday Homes in Stock Island

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Outdoor dining

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (184)
"Loved this ocean view property! Very nice location and very comfortable home!"
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Spacious home with pool & balcony - 1 block from Duval Street
Property grounds

Spacious home with pool & balcony - 1 block from Duval Street

9.2 out of 10, Wonderful, (72)
"Great pool and location. "
The price is AU$1,759
includes taxes & fees
1 Dec - 2 Dec
Spacious home with pool & balcony - 1 block from Duval Street
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Fridge, microwave, oven, stovetop

PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL

9.8 out of 10, Exceptional, (10)
"Property was clean with everything we needed, including linens and beach towels. Kitchen was fully equipped. The upstairs was a little too warm at night, but it was in the 90's every day during our stay, so we could understand this. One of the twin beds has a mattress that was very uncomfortable, and needs replaced. We have a vacation rental of our own and we were well pleased with this property. We would recommend! Thank you for the little longer checkout time, as the hurricane changed...
The price is AU$2,255
includes taxes & fees
11 Dec - 12 Dec
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
Exterior detail

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

9.2 out of 10, Wonderful, (177)
"The location was great. Close to everything but still quiet. The condo is more dated and worn than we expected. There was a strong musty smell as soon as we opened the door and adjusting the a/c didn't help. Maybe it's typical of the area but it really bothered my allergies. "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
Beach nearby, beach towels

STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.

10.0 out of 10, Exceptional, (150)
"Perfect location, perfect house, and perfect place for a 60th birthday celebration. Words cannot describe how much the owner has made this property a little piece of paradise. Our first time in Key West and we had a beyond fantastic week, even on my husband’s birthday that was on the day Hurricane Helene happened. My husband was surprised with a birthday gift on arrival. We definitely give this place and owners a 10 out of 10. "
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (30)
"Nice location very close to everything and close enough to Duval St. Unit itself was in good condition and the kitchen stocked pretty good but was missing dish cloths, dish towels and dishwasher detergent. None of the grills on the property were functional. Host was very responsive the entire process. Would stay there again"
The price is AU$591
includes taxes & fees
3 Dec - 4 Dec
Poolside Cottage #411
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, (200)
"Very walkable. Cozy comfortable place. Cute and safe neighborhood. Setup well for cooking. AC pumps some good cold air. "
Feb 3-10 $245 off the rates close beach full kitchen & patio
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Property grounds

Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

9.0 out of 10, Wonderful, (222)
"Nice place ,great ammenties very close to duval street, cuban place right on the corner by it is great "
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Kelly's Kabin - Adorable Private Summerland Key Cottage
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (104)
"The property is as described. Good location. We would stay there again."
The price is AU$946
includes taxes & fees
12 Dec - 13 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage
Poolside Paradise | Private Oasis, 1 Block to Duval!
Pool

Poolside Paradise | Private Oasis, 1 Block to Duval!

9.2 out of 10, Wonderful, (11)
"Great location 1/2 block from Duval. Lots of great towels, and pillows! I didn’t know this is two units connected but no connecting door, you access back unit via the pool. We needed both sofa beds but one had broken springs and was unusable. The floors hadn’t been mopped and all of my kids had black feet from walking around barefoot. If you are planning to cook you might want to bring a decent frying pan and a sharp knife. They have plenty of knives but none sharp. The grill didn’t work and...
The price is AU$1,519
includes taxes & fees
1 Dec - 2 Dec
Poolside Paradise | Private Oasis, 1 Block to Duval!
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
A heated pool

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

9.6 out of 10, Exceptional, (74)
"My brother and I hadn’t seen each other for quite a while. This place offered us so much comfort and convenience. GREAT place to stay. We will be back. Thank you. "
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Captain's Daughter: Oversized home for the whole family w/private pool & dock
A heated pool

Captain's Daughter: Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (117)
"House was amazing! The house was clean and stocked with basic necessities even found a few tide pods for laundry. Perfect for a girls weekend party of 12. We will definitely rent this house again on our next trip to Key West!"
Captain's Daughter: Oversized home for the whole family w/private pool & dock
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
A heated pool

ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking

9.8 out of 10, Exceptional, (59)
"Elizabeth’s Secret was a perfect cozy home to celebrate our daughter’s 21st birthday and spend fun/quality time with she and her brother/ his girlfriend. We always rent bikes which gets us around town easily to all of our Key West favorites and continue to explore new spots. The pool was enjoyable morning, noon and night. As well as cooking and grilling the fresh fish we caught Monday on the fishing charter we had booked. Off street parking, coolers to use while kayaking at Lazy Dog, blender...
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

9.8 out of 10, Exceptional, (198)
"The location was perfect and the unit was clean and comfortable. The key lime pie from the hosts was a nice touch."
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Terrace/patio

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

9.8 out of 10, Exceptional, (21)
"Clean, cozy and cute "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Fridge, microwave, coffee/tea maker, toaster

Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location

9.0 out of 10, Wonderful, (169)
"My sister and I rented the place for ourselves and our 4 young adult kids (ranging from 18-21), and we had a very nice time. The AC is not really "central", has free-standing units in 2 of the bedrooms that vent outside, but they are well installed and do the trick, if a bit tricky to regulate the temperature correctly initially. The place is a typical Key West bungalow that feels like some shoeboxes were nailed together, and the back yard is even smaller than expected. Location is great, we did...
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Terrace/patio

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

9.8 out of 10, Exceptional, (96)
"We had a great stay - the property was well kept and the host was very good in responding to us quickly. The home is very close to everything - a quick 5 minute drive to the east side of Key West. Great community pool and quiet neighborhood. "
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
Terrace/patio

ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!

9.8 out of 10, Exceptional, (56)
"Perfect location , very enjoyable house ."
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
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, (26)
"Super nice place Comfortable Couch Comfortable Bed"
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Mermaid's Retreat at Coral Hammock Key West Island living at its best
A heated pool

Mermaid's Retreat at Coral Hammock Key West Island living at its best

Mermaid's Retreat at Coral Hammock Key West Island living at its best
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, (104)
"Nice for affordable price "
The price is AU$448
includes taxes & fees
3 Dec - 4 Dec
Aqua Lodges at Hurricane Hole Marina
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds

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

10.0 out of 10, Exceptional, (14)
"BOOK THIS BOAT!!!’ TOP 10 vacations ever!!! Hannah was so accommodating and onboarded us to The Grand Admiral. Beautiful marina with easy access to The Perry hotel and bar, making it a very very comfortable stay. And then the excursion 😍!! Captain Jeff made our day exceptional. We encountered dolphins, lounged on the sandbar, and grilled while watching a breathtaking sunset. We will be making this an annual trip! Thank you Captain Jeff for the best day ever."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Luxury 62' Yacht! In a Beautiful Resort
Outdoor pool, a heated pool

Luxury 62' Yacht! In a Beautiful Resort

10.0 out of 10, Exceptional, (7)
"Excellent boat, excellent stay. Would love to return."
Luxury 62' Yacht! In a Beautiful 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.
Beautiful view of the beach with palm trees

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