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

Vacation Rentals in Stock Island

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"The stay was beautiful "
The price is CA $80
CA $321 total
includes taxes & fees
Aug 12 - Aug 13
Aqua Lodges at Hurricane Hole Marina

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

7.4 out of 10, Good, (10)
"We were here celebrating 55th birthdays and had a blast. Great location and communication with Capt. We will return for sure, hoping to make it an annual get together."
The price is CA $241
CA $860 total
includes taxes & fees
Aug 13 - Aug 14
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Living the Dream Key West Style

10.0 out of 10, Exceptional, (21)
"Great hosts and great accommodations!"
The price is CA $370
CA $464 total
includes taxes & fees
Aug 13 - Aug 14
Living the Dream Key West Style

Super-cozy boat in 5 Star Key West Marina.

10.0 out of 10, Exceptional, (1)
"We had the best experience in this charming boathouse - it was just the right size for our group of four. From the moment we stepped inside, we felt right at home in its cozy and comfortable atmosphere, it felt like a bit of home away from home, but with the added novelty of being right on the water. Lori's thoughtful touches throughout made the small space extra inviting and relaxing. She and her husband were amazing hosts and always responded quickly to answer any of our questions, I loved...
Super-cozy boat in 5 Star Key West Marina.

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

8.8 out of 10, Excellent, (54)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew

The price is CA $8,242
CA $10,442 total
includes taxes & fees
Aug 13 - Aug 14
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew

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 $343
CA $696 total
includes taxes & fees
Aug 13 - Aug 14
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 $428
CA $816 total
includes taxes & fees
Aug 20 - Aug 21
Grand Marina Suite by Brightwild Waterfront

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (307)
"We had a nice stay. The property was in a great location."
The price is CA $323
CA $403 total
includes taxes & fees
Aug 24 - Aug 25
Hyatt Vacation Club at Sunset Harbor, Key West

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

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is CA $126
CA $451 total
includes taxes & fees
Aug 12 - Aug 13
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (394)
"this was exactly as advertised and close to all the action"
The price is CA $122
CA $313 total
includes taxes & fees
Aug 13 - Aug 14
Steps from Duval, Pool on Site & Bikes Included!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"
Heart of Downtown Key West Cottage With Off-Street Parking

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

9.6 out of 10, Exceptional, (139)
"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 $339 total
includes taxes & fees
Aug 18 - Aug 19
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

9.6 out of 10, Exceptional, (8)
"The units were perfect and the customer service was amazing. "
The price is CA $353
CA $1,152 total
includes taxes & fees
Aug 31 - Sep 1
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

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 $130
CA $381 total
includes taxes & fees
Aug 13 - Aug 14
Claude Monet Suite | Cozy Studio with Pool & Patio Access!

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

9.6 out of 10, Exceptional, (13)
"Great place to stay! Very clean and steps to Duval Ave."
The price is CA $171
CA $554 total
includes taxes & fees
Aug 10 - Aug 11
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

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 $121
CA $326 total
includes taxes & fees
Aug 12 - Aug 13
WHITEHEAD 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, (179)
"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!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

9.6 out of 10, Exceptional, (141)
"Very clean, great location and wonderful amenities!"
The price is CA $125
CA $331 total
includes taxes & fees
Aug 13 - Aug 14
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (19)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is CA $126
CA $448 total
includes taxes & fees
Aug 27 - Aug 28
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
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