Stock Island Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Stock Island

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"The stay was beautiful "
The price is CA $117
CA $364 total
includes taxes & fees
Aug 28 - Aug 29
Aqua Lodges at Hurricane Hole Marina

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

8.8 out of 10, Excellent, (55)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: great place, great location! we'll be back year after year!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Living the Dream Key West Style

10.0 out of 10, Exceptional, (21)
"Great hosts and great accommodations!"
The price is CA $372
CA $473 total
includes taxes & fees
Aug 28 - Aug 29
Living the Dream Key West Style

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

7.6 out of 10, Good, (10)
"The ideal getaway, I brought a grill and a pan and did all the cooking outside on the deck. Took paddle boards through mangrove tunnels and saw tons of fish. Had a baby sea turtle swim up to the boat. "
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

7.8 out of 10, Good, (22)
"Loved everything about the stay, "
The price is CA $346
CA $701 total
includes taxes & fees
Aug 28 - Aug 29
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Grand Marina Suite by Brightwild Waterfront

2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
The price is CA $430
CA $820 total
includes taxes & fees
Sep 4 - Sep 5
Grand Marina Suite by Brightwild Waterfront

TRAVEL THE KEYS OR JUST RELAX AT THE DOCK

9.4 out of 10, Exceptional, (28)
"The marina is the perfect location! There are 4 bedrooms so it is perfect for a group of friends (all individual beds except the master). The kitchen was well stocked to make all means and the grill on the top deck was great!"
TRAVEL THE KEYS OR JUST RELAX AT THE DOCK

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (312)
"EXCELENT LOCATION AND SUNSET VIEW"
The price is CA $364
CA $449 total
includes taxes & fees
Sep 3 - Sep 4
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (397)
"this was exactly as advertised and close to all the action"
The price is CA $123
CA $315 total
includes taxes & fees
Sep 4 - Sep 5
Steps from Duval, Pool on Site & Bikes Included!

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (140)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is CA $131
CA $341 total
includes taxes & fees
Aug 28 - Aug 29
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.4 out of 10, Exceptional, (11)
"Great time staying there "
The price is CA $122
CA $323 total
includes taxes & fees
Sep 2 - Sep 3
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.8 out of 10, Exceptional, (18)
"Great place will rent again "
The price is CA $122
CA $323 total
includes taxes & fees
Sep 1 - Sep 2
THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (181)
"Place is centrally located which is ideal for walking from place to place. House was very clean and had everything needed for my time spent there"
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is CA $112
CA $433 total
includes taxes & fees
Sep 9 - Sep 10
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Claude Monet Suite | Cozy Studio with Pool & Patio Access!

9.4 out of 10, Exceptional, (20)
"Great location. Everything was perfect!"
The price is CA $115
CA $360 total
includes taxes & fees
Sep 24 - Sep 25
Claude Monet Suite | Cozy Studio with Pool & Patio Access!

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

9.2 out of 10, Wonderful, (16)
"I was initially worried because I normally would only book with a property that had quite a bit of reviews. I'm glad I trusted my instincts to go with the Inn on Fleming! The room looked exactly as pictured. The whole lodge had a cute charm to it. Perfect place to stay when visiting the keys."
The price is CA $172
CA $400 total
includes taxes & fees
Sep 2 - Sep 3
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (134)
"May not be a better location"
Heart of Downtown Key West Cottage With Off-Street Parking

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (15)
"Great place to stay! Very clean and steps to Duval Ave."
The price is CA $136
CA $522 total
includes taxes & fees
Sep 10 - Sep 11
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (296)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

9.6 out of 10, Exceptional, (188)
"The location was perfect for exploring and getting places in key West. It had a relaxing vibe that was perfect for vacation. "
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Stock Island Hotel Reviews

Find out more about Stock Island

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stock Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stock Island vacation rentals we have selected for you start as low as CA $112 per night. Entering your travel dates in the search wizard 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.