Stock Island Vacation Rentals from $273: Search Short-Term Rentals

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In two weeks

In two months

In three months

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Our top choices for Stock Island vacation rentals

Aqua Lodges at Hurricane Hole Marina

Stock Island

Stacy

$274 nightly

Jun 8 - Jun 9

Total with taxes and fees

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

Stock Island

Leigh P.

$384 nightly

Jun 2 - Jun 3

Total with taxes and fees

Affordable, Adventurous Houseboat on-the-water in Key West Florida

Stock Island

$283 nightly

Jun 19 - Jun 20

Total with taxes and fees

Grand Marina Suite by Brightwild Waterfront

Stock Island

Pawel

$508 nightly

Jun 2 - Jun 3

Total with taxes and fees

Paradise found

Stock Island

anita b.

$551 nightly

Jun 2 - Jun 3

Total with taxes and fees

Key West Sailboat Getaway

Stock Island

$218 nightly

Jun 8 - Jun 9

Total with taxes and fees

Living the Dream Key West Style

Stock Island

Scott

$364 nightly

Jun 2 - Jun 3

Total with taxes and fees

Docked in Paradise

Stock Island

Susan T.

$437 nightly

Jun 2 - Jun 3

Total with taxes and fees

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Top Stock Island Hotel Reviews

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"Great Stay with Excellent Shuttle Service! We recently stayed for 1 night during our Key West vacation and had a very pleasant experience overall. Location – The hotel is conveniently located close to the Key West downtown area. What really stood out was the complimentary shuttle service that runs every hour to Downtown/Mallory Square—extremely convenient and saved us from driving and paying for parking. Cleanliness – The hotel was very clean and well maintained throughout our stay. Property Condition & Amenities – The property looks new. The lobby is stylish and gives the feel of a more upscale hotel. Amenities like the mini fridge and free ice vending machine were very useful. Room Comfort – The room was little, smaller compared to similar hotels in other locations. The mini fridge came in handy for storing our drinks and beverages. Hospitality (Front Desk) – The front desk staff were very welcoming and helpful. They clearly explained the hotel facilities and the shuttle service, which made our stay even smoother. Highlight of the Stay The free shuttle service to downtown Key West/Mallory Square was definitely the highlight. We used it multiple times and it made getting around incredibly easy and stress-free. Final Thoughts Overall, a great hotel with modern amenities, friendly staff, and an excellent shuttle service. We would definitely recommend this hotel to anyone visiting Key West!"

The Laureate Key West

10/10 Excellent

"Our stay at Laureate Key West was simply exceptional. From the moment we arrived, we felt welcomed by the friendly and professional staff. The facilities were spotless, the rooms were comfortable, modern, and very clean, and every detail was thoughtfully designed to ensure a relaxing experience. The location is excellent, allowing us to enjoy everything Key West has to offer while staying in a peaceful and welcoming environment. The customer service exceeded our expectations; the entire team was attentive, helpful, and always willing to assist with a smile. Without a doubt, this was one of the best hotel experiences we have ever had. We highly recommend Laureate Key West to anyone looking for comfort, quality, and an unforgettable stay in the Florida Keys. We can’t wait to return!"

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good

"Everything was clean, staff friendly and helpful. Shuttle system works perfectly. They have some nice handouts and warm cookies for the guests by reception. Just one inconvenience or complain - the room 377 had the worst view. I believe there were better options than a dumpster."

Blue Flamingo Resort Key West

2/10 Terrible

"Very disappointing, read why. If a hot tub/real restaurants are important/necessary to you, do not book here. They claim there is a hot tub on the premises, it is actually a 7 minute walk to a completely different hotel. (The properties are owned by the same company,this is false advertising. When we did make it there, the hot tub jets were not working & maintenance was aware of the situation previously said another couple. I suppose it was not guest priority. The original hot tub in the pool area is now a plastic grass circle in front of the “gym”. When I addressed this issue of via text, I was brushed off for 3 days telling me they were “relaying the message to the complaint team”, which I’m sure didn’t exist & was only computer generated. Who wants to walk thru an abandoned parking lot, thru a row of palm trees, at dark just to sit in a hot pool? Is that even safe? When I checked out, the site manager,Adrian, asked about our stay. I told him of my disappointment considering I booked this trip to use a hot tub several times a day for my muscle condition. After being confrontational, he gave me a $50 resort fee for 1 day although my stay was 3.Do not be fooled, tiki bars are the “restaurants” with the same food everyday & the one tikibar at the main pool actually shuts down @5pm. Although Expedia says they give you a $15 food/beverage credit, the tiki bartender said it comes off the final bill, it did not. Courtyard is great however gets locked down 1030 so no after hour fun"

Southernmost Beach Resort and Guesthouses

8/10 Good

"Overall, we were very happy with our stay. The staff were extremely responsive to text requests and the food and bar beverages were very good and fairly priced. My only feedback is 1 - I purposely booked this hotel because it was one of the only ones with private beach access. Unfortunately, the seaweed was PILED higher the shoreline and it STUNK so badly it was making we gag. I think they could have done more to ensure the beach was properly cleared and people could enjoy. No one were sitting in beach chairs, likely for the same reasons. We spent zero time on the beach and the pool chairs were all taken plus the pool was mobbed with people and looked pretty gross. The other feedback is that check in and the desk processes seemed to take a long time, even with a lot of staff helping."

Hampton Inn Key West FL

10/10 Excellent

"Clean room with great ocean view! Great breakfast with great daily variety! Great gym! Great pool with poolside shack bar and grill! Staff were great, helpful with any questions and very friendly! Van service to airport and downtown on time and great drivers! We will be back!!! 5 stars!"

Find out more about Stock Island

Everything you need to know about Stock Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stock Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stock Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stock Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stock Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Stock Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $273 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stock Island rentals

At Expedia, we put the best Stock Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stock Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stock Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stock Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Room 1

Check prices for these dates

Our top choices for Stock Island vacation rentals

Aqua Lodges at Hurricane Hole Marina

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

Affordable, Adventurous Houseboat on-the-water in Key West Florida

Grand Marina Suite by Brightwild Waterfront

Paradise found

Key West Sailboat Getaway

Living the Dream Key West Style

Docked in Paradise

Grand Marina Suite - Poolside & Waterfront Condo

Cozy Houseboat

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

Charming 1-Bedroom, Sailboat in wonderful Key West

Waterfront & Heated Pool - Break Awai Floating Villa

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

Waterfront & Heated Pool - Away Awai Floating Villa

Slice of Paradise

Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West

Living Life Dockside

Spacious 3-bedroom townhome on Stock Island with resort style pool.

Find vacation rentals that suit your style

Top Stock Island Hotel Reviews

Hilton Garden Inn Key West / The Keys Collection

The Laureate Key West

DoubleTree Resort by Hilton Grand Key - Key West

Oceans Edge Key West Resort, Hotel & Marina

Blue Flamingo Resort Key West

Southernmost Beach Resort and Guesthouses

Hampton Inn Key West FL

The Perry Hotel & Marina Key West

Opal Key Resort & Marina, Key West

Find out more about Stock Island

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