Stock Island Holiday Rentals

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Holiday Rentals in Stock Island

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (162)
"The stay was beautiful "
The price is NZ$437
includes taxes & fees
29 Sept - 30 Sept
Aqua Lodges at Hurricane Hole Marina

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 NZ$875
includes taxes & fees
28 Sept - 29 Sept
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

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

6.6 out of 10, (12)
"Unfortunately this stay was very disappointing. The marina was awesome. Tessa was awesome. The boat itself was disgusting. The pictures are very deceiving. What you see is not what you get. "
The price is NZ$596
includes taxes & fees
28 Sept - 29 Sept
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Living the Dream Key West Style

9.8 out of 10, Exceptional, (24)
"Great hosts and great accommodations!"
The price is NZ$589
includes taxes & fees
4 Oct - 5 Oct
Living the Dream Key West Style

1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

The price is NZ$589
includes taxes & fees
28 Sept - 29 Sept
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

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

8.8 out of 10, Excellent, (57)
"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!

Grand Marina Suite by Brightwild Waterfront

2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
The price is NZ$1,249
includes taxes & fees
13 Oct - 14 Oct
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, (314)
"Great hotel with excellent location "
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (402)
"this was exactly as advertised and close to all the action"
The price is NZ$389
includes taxes & fees
30 Sept - 1 Oct
Steps from Duval, Pool on Site & Bikes Included!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (183)
"Great location; excellent property management "
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

8.8 out of 10, Excellent, (231)
"Property was cute and in a great location! "
The price is NZ$352
includes taxes & fees
29 Sept - 30 Sept
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

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

10.0 out of 10, Exceptional, (22)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is NZ$543
includes taxes & fees
28 Sept - 29 Sept
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

10.0 out of 10, Exceptional, (189)
"Outstanding place to stay, centrally located!"
The price is NZ$3,393
includes taxes & fees
28 Oct - 29 Oct
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (136)
"Great Location, Free Parking, comfortable beds"
Heart of Downtown Key West Cottage With Off-Street Parking

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

9.6 out of 10, Exceptional, (188)
"Bucket list trip. Great location. Property was just what was expected. Perfect for 2!"
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

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

9.6 out of 10, Exceptional, (141)
"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 NZ$417
includes taxes & fees
8 Oct - 9 Oct
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (819)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (4)
"Beautiful property, perfectly located, and one of the best VRBO experiences we have ever had."
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

9.6 out of 10, Exceptional, (17)
"Short walk to Duval street, quiet and very clean and comfortable."
The price is NZ$408
includes taxes & fees
6 Oct - 7 Oct
GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!
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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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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stock Island holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stock Island holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stock Island holiday rentals we have selected for you start as low as NZ$352 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 holiday 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 holiday.

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.