Search Vacation Homes in Stock Island

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 675 Vacation Homes in Stock Island with updated reviews, rates, and availability.

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

9.0 out of 10, Wonderful, (35)
"Stay was fun and place was clean. Could use a little improvement. Couch was u comfortable and coffeetable broken. The bikes def need some attending to. The table outside is very nice but a little too high; needs adjusting. Hot tub was wonderful and it was quiet for sleeping. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Spec.Feb.24-Mar 1 @229+ 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 @229+ w. 3 night stay close beach

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is SAR 1,268
SAR 1,956 total
includes taxes & fees
3 Mar - 4 Mar
Poolside Cottage #411

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

9.4 out of 10, Exceptional, (33)
"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 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio

9.6 out of 10, Exceptional, (209)
"Had enjoyable three day visit in Key West. Stayed in comfortable little VRBO house apartment in southern part of Old Town. "
Feb 2-5 spec 279.lodg. + extras Close to beach w full kitchen. & patio

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

9.6 out of 10, Exceptional, (177)
"This property was perfect. The house itself is lovely and has a great set up. 4 bedrooms (one is in a little attached cottage outside). The pool is a very nice addition. The home is located a little bit off the beaten track, so it is quiet. It is in walking distance of everything. We would definitely stay here again!walkingof "
CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!

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

9.4 out of 10, Exceptional, (55)
"This house was exactly what our group was looking for. Loved the location and proximity to Duval Street. Also loved the outdoor pool area for hanging out. Would def recommend. "
Villa Déjà vu Key West - Steps Off Duval w Private Pool

Coastal Comfort; Waterfront Luxury Home with private pool!

9.4 out of 10, Exceptional, (64)
"excellent location, quiet from the town noise, but close proximity, and access to all the Key West points. great rental house amenities for up to 8 people , and great ocean view "
Coastal Comfort; Waterfront Luxury Home with private pool!

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

10.0 out of 10, Exceptional, (5)
"The property was so beautiful and clean! It was close proximity to everything you want to do in Key West. We did notice a small leak on the first floor balcony and it was a little slippery.But overall loved!!!"
The price is SAR 1,310
SAR 3,228 total
includes taxes & fees
26 Feb - 27 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!

9.8 out of 10, Exceptional, (90)
"Clean, roomy, comfortable. Adequate seating and dishes for 6 adults. Great mattresses and pillows. "
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

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

9.6 out of 10, Exceptional, (26)
"Very comfortable unit to stay near Key West.Beautiful water view.Just 15-20 min from downtown .Will stay again . "
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very Good, (19)
"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

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

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

10.0 out of 10, Exceptional, (4)
"Rick and team were awesome and exceptional throughout the whole stay! Nice house!! "
The price is SAR 3,705
SAR 7,002 total
includes taxes & fees
18 Mar - 19 Mar
Conch Cove - 3br/3ba with private heated pool and private parking

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!

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!

9.6 out of 10, Exceptional, (201)
"Loved the location. House was really comfortable and well stocked with everything we needed. Pool area very tropical and private and although our weather was unusually a bit cool, we enjoyed the outside area. The property manager was very responsive to any communication and we even got to check in early as soon as we landed which was an excellent perk. Definitely would stay here again on our next trip. "
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!

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

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

10.0 out of 10, Exceptional, (216)
"Everything was great! Thanks!"
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.
Don't see what you're looking for?
See all available properties in Stock Island
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Stock Island

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (117)
"Awesome place, with a cool location right near the mangroves. Has a little restaurant and bar and gift shop, as well as kayak tours and rentals. Paddle boards too. We liked the visits from the manatees and nurse sharks near the fish cleaning station. Only negatives I have are that the ceiling fan chains were broken and harder to reach, some of the pillows were a bit yellowish and have seen better days and multiple devices like the Air conditioner and TV remotes batteries were dead, but they...
The price is SAR 1,009
SAR 1,764 total
includes taxes & fees
3 Mar - 4 Mar
Aqua Lodges at Hurricane Hole Marina

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

10.0 out of 10, Exceptional, (4)
"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

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

10.0 out of 10, Exceptional, (3)
"I didn’t really know what I was getting into, but I’m glad I didn’t cancel. This was such a beautiful experience to have shared with just myself. The bed was comfortable and I slept really well both nights. The second night, I had to rent a kayak from the marina (40) to get to the house. It was a beautiful sunset paddle. It’s easy enough, but even as an experienced paddler, it’s about 20 minutes . I had to leave around 5am to catch my flight and paddled back to the marina in pitch black. It was...
The price is SAR 713
SAR 1,140 total
includes taxes & fees
27 Feb - 28 Feb
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
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.