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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 818 Vacation Homes in Stock Island with updated reviews, rates, and availability.

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, (192)
"This home is great location , fits party of up to 6 perfectly "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT 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, (95)
"Had a blast. Great location and accommodation "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes
Terrace/patio

NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes

9.0 out of 10, Wonderful, (161)
"The place was cute; we had everything we needed and it was convenient to all the fun w/o being too close to all the noise and busyness of Duval St. Loved it!"
NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen
Exterior detail

Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen

9.6 out of 10, Exceptional, (214)
"This property is centrally located and we easily biked around to everything. There were restaurants and a gas station in walking distance. The surrounding neighborhood is quiet and neighbors were friendly and quiet. The bed was so comfortable, and the adjustable head of bed was so nice! I feel the price may have been on the high side due to Spring Break. I’d like to stay again and hope the price may be more reasonable in other times of the year.Overall, we loved the place and the location."
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Property grounds

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

8.8 out of 10, Excellent, (44)
"We just needed a place for a couple of nights so that we could make the day trip to Dry Tortugas NP. This fit the bill! It wasn’t fancy but we felt safe and were easily able to fit our family of 5. But I wouldn’t have stayed for longer than 2 nights as we would’ve been cramped. We had everything we needed and all the necessary instructions ahead of time. And the view off of the back deck was pretty incredible! Also, if you don’t have a sound machine, be prepared for a rooster alarm clock!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
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, (126)
"We've stayed at this property 3 times and we love it. Prefect size. Great communication "
Captain's Daughter: Oversized home for the whole family w/private pool & dock
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
A heated pool

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

9.6 out of 10, Exceptional, (77)
"Perfect house with a great pool and amazing location to Duval and grocery store across the street. Highly recommend."
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
Fridge, microwave, oven, stovetop

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

9.8 out of 10, Exceptional, (179)
"Nothing but great things to say about the house, location and communications with property managers. And what's not to like about having 3 bathrooms, especially with a larger family like ours. Just walk in and start enjoying key west. It's half a block from Duval St. and about a 5 minute walk to Southern Most."
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
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, (18)
"The property was as described. The location was perfect and quiet. We'd love to the pool and hanging out there. Customer service was outstanding."
The price is SAR 1,310
SAR 3,227 total
includes taxes & fees
20 Apr - 21 Apr
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
A heated pool

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

9.8 out of 10, Exceptional, (216)
"The house had everything we needed. Convenient location. "
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
A heated pool

SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!

9.8 out of 10, Exceptional, (182)
"Absolutely a gorgeous property and fantastic location. Key West is our favorite place to visit. This house, along with the property manager, made this year's visit the best yet! Thanks for a great birthday and we look forward to booking this property again next year"
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool
Fridge, microwave, oven, stovetop

NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool

10.0 out of 10, Exceptional, (14)
"We loved our location, the house and Key West!"
NEW listing!! Luxurious Island Pearl, 2 Bed/2 Bath Home near Duval - Pool
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (145)
"After reading the other reviews I packed my air mattresses… didn’t need them the beds were fine. The patio rail is fixed based on a previous post. Only 1 working TV but not a big deal. 2 built in ovens but neither works, not ideal for larger family to use a small toaster oven. The place was clean and you can’t beat the location. "
The price is SAR 1,126
SAR 2,351 total
includes taxes & fees
25 Apr - 26 Apr
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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!

9.8 out of 10, Exceptional, (81)
"This was the perfect place for our family to stay. It was very clean and great location. We will be back for sure!"
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Perfect Location, Private Heated Pool & Pristine Luxury Home!
Outdoor pool, a heated pool

Perfect Location, Private Heated Pool & Pristine Luxury Home!

10.0 out of 10, Exceptional, (168)
"This home is fully dialed in. Beautiful finishings, all the towels, sunscreen, and pool accessories you could ask for, and a perfect layout with gorgeous private pool and beautifully landscaped backyard space. Would definitely stay here again!"
The price is SAR 3,752
SAR 7,318 total
includes taxes & fees
13 May - 14 May
Perfect Location, Private Heated Pool & Pristine Luxury Home!
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Property grounds

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (137)
"Nice location. Comfortable place although the couch and living room chair were old and stained. "
The price is SAR 1,032
SAR 2,260 total
includes taxes & fees
20 Apr - 21 Apr
Cudjoe Cottages, swimming pool, just 20 miles from Key West
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
A heated pool

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!

10.0 out of 10, Exceptional, (82)
"Location. Location. Location. One block off Duval St and near everything. We rented a car but didn’t need it. Walked everywhere. "
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
3 bedrooms, iron/ironing board, WiFi, bed sheets

Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub

9.8 out of 10, Exceptional, (146)
"This property is amazingly situated and very well appointed. We have stayed here several times, and it does not disappoint in any respect. The convenience of location (and parking) is amazing and cannot be beat. It's enough off the main street to be comfortably quiet, but you can still enjoy the live music at a level which does not impede conversation while outside. Super clean with high end finishes. The private pool is mostly shaded, which is wonderfully refreshing after being out and about."
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Fridge, microwave, oven, stovetop

**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

9.8 out of 10, Exceptional, (86)
"Sam, Charlie and Vic were great"
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very Good, (89)
"We stayed for my husband’s surprise 40th birthday weekend. Kazi was an amazing host and made the booking/arrival/departure process so easy. His hospitality was amazing and we can’t wait to come back."
Private Secluded Ocean View & Pool Near Key West
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
Deluxe Bungalow | Private kitchen

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (128)
"It was a great experience being on a houseboat."
The price is SAR 436
SAR 1,119 total
includes taxes & fees
23 Apr - 24 Apr
Aqua Lodges at Hurricane Hole Marina
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
1 bedroom, internet, bed sheets

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

10.0 out of 10, Exceptional, (6)
"This was a perfectly unique and special experience. Matt was amazing to work with for arrival and departure. Timely and exactly as Liam said everything would be. They put special touches on the stay, ice bucket, two waters, beach towels, our name on a cute sign, a cooler, extra covers and everything you need for a Glamping stay on the water! Camping at its best! We definitely plan to come back and will recommend this stay to our friends. This is perfect for outdoor lovers and adventurous people...
The price is SAR 634
SAR 1,045 total
includes taxes & fees
28 Apr - 29 Apr
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Terrace/patio

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

9.2 out of 10, Wonderful, (5)
"Was just a teaser initial trip to Key West but staying on the water was awesome! Beautiful views and great amenities. Kevin and Captain Philip were great throughout the whole process including great local recommendations! One thing to note, if you are 6’ plus, will need to watch your head and the steps downstairs require concentration. As a shorter person (barely 5’!) it all worked perfectly for me! Look forward to staying again and taking the boat out next time! "
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
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.