Stock Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Stock Island vacation homes

Great Family Vacation Rental.

Great Family Vacation Rental.
Stock Island
8.8 out of 10, Excellent, (15 reviews)
"Enjoyed staying here super clean and well stocked!"
Canada
Kirsty E.
Great Family Vacation Rental.

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

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
10.0 out of 10, Exceptional, (17 reviews)
"This property was very clean and comfortable. I would definitely stay here again. The pool was very nice "
United States
L G.
The price is CA $614
CA $1,581 total
includes taxes & fees
Mar 7 - Mar 8
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

Coral Garden by AvantStay | Great Location w/ Balcony & Shared Pool

Coral Garden by AvantStay | Great Location w/ Balcony & Shared Pool
Stock Island
9.6 out of 10, Exceptional, (8 reviews)
"Nice place enjoyed stay"
United States
Nancy S.
The price is CA $664
CA $1,497 total
includes taxes & fees
Mar 6 - Mar 7
Coral Garden by AvantStay | Great Location w/ Balcony & Shared Pool

3-bedroom townhome in Key West with fitness room, WiFi

3-bedroom townhome in Key West with fitness room, WiFi
Stock Island
9.6 out of 10, Exceptional, (9 reviews)
"The property was clean, the location was convenient to the beach, a CVS, and Roostica which had delicious pizza and wings. "
United States
Jason K.
The price is CA $859
CA $1,781 total
includes taxes & fees
Mar 9 - Mar 10
3-bedroom townhome in Key West with fitness room, WiFi

Unique Waterfront Yacht in 5 star resort. Pools, Gym & Downtown Shuttle

Unique Waterfront Yacht in 5 star resort. Pools, Gym & Downtown Shuttle
Stock Island
The price is CA $499
CA $893 total
includes taxes & fees
Mar 29 - Mar 30
Unique Waterfront Yacht in 5 star resort. Pools, Gym & Downtown Shuttle

$$ SAVE BIG $$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

$$ SAVE BIG $$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (85 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is CA $271
CA $678 total
includes taxes & fees
Mar 5 - Mar 6
$$ SAVE BIG $$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very good, (1 review)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is CA $342
CA $918 total
includes taxes & fees
Mar 4 - Mar 5
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (8 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is CA $272
CA $822 total
includes taxes & fees
Mar 11 - Mar 12
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

$$ SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

$$ SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
"Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. "
United States
Lauren D.
The price is CA $340
CA $760 total
includes taxes & fees
Mar 11 - Mar 12
$$ SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.8 out of 10, Good, (14 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is CA $338
CA $702 total
includes taxes & fees
Mar 7 - Mar 8
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is CA $477
CA $923 total
includes taxes & fees
Mar 11 - Mar 12
Spanish Queen @Venture Out, Cudjoe Key

Fun in the Sun in Cudjoe Key! #51

Fun in the Sun in Cudjoe Key! #51
Cudjoe Key
8.6 out of 10, Excellent, (9 reviews)
"This was a beautiful"
United States
Debbie A.
The price is CA $314
CA $944 total
includes taxes & fees
Mar 9 - Mar 10
Fun in the Sun in Cudjoe Key! #51

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

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
9.0 out of 10, Wonderful, (160 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
The price is CA $477
CA $952 total
includes taxes & fees
Mar 26 - Mar 27
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
The price is CA $375
CA $702 total
includes taxes & fees
Mar 31 - Apr 1
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (12 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is CA $322
CA $886 total
includes taxes & fees
Apr 2 - Apr 3
Island Time #110 Ocean Views - Cudjoe Key

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is CA $358
CA $931 total
includes taxes & fees
Apr 2 - Apr 3
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very good, (123 reviews)
"Great experience "
United States
Peyton S.
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
The price is CA $473
CA $1,077 total
includes taxes & fees
Mar 31 - Apr 1
Starlight Serenity - Hideaway with Stunning Views

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is CA $1,497
CA $2,563 total
includes taxes & fees
Mar 24 - Mar 25
Private and Exclusive Florida Keys Getaway

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is CA $1,090
CA $2,332 total
includes taxes & fees
Mar 9 - Mar 10
Capmar House at Lunara Bay
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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

Stock Island Vacation Homes information

Number of reviews
635
Accommodation
828 Vacation Homes
Lowest Price
CA $678
Highest Price
CA $2,563

Explore a world of travel with Expedia