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

Next weekend
In two weeks

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 $81
CA $323 total
includes taxes & fees
Aug 11 - Aug 12
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 $385
CA $1,020 total
includes taxes & fees
Aug 12 - Aug 13
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

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

10.0 out of 10, Exceptional, (7)
"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. "
The price is CA $223
CA $372 total
includes taxes & fees
Aug 7 - Aug 8
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

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, (52)
"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 $8,272
CA $10,480 total
includes taxes & fees
Aug 14 - Aug 15
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew

Grand Marina Suite by Brightwild Waterfront

2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
The price is CA $429
CA $817 total
includes taxes & fees
Aug 4 - Aug 5
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 $311
CA $389 total
includes taxes & fees
Aug 10 - Aug 11
Hyatt Vacation Club at Sunset Harbor, Key West

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (393)
"this was exactly as advertised and close to all the action"
The price is CA $123
CA $314 total
includes taxes & fees
Aug 12 - Aug 13
Steps from Duval, Pool on Site & Bikes Included!

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 $134
CA $458 total
includes taxes & fees
Aug 12 - Aug 13
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

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, (137)
"We stayed in the Cohiba and it was so cute! Felt private and to ourselves. Everyone we met on site was so friendly. Having the pool on property and private was such a blessing. There was an incident in the main house bathroom that was quickly responded to by property management. Would stay again! Thank you! "
The price is CA $136
CA $347 total
includes taxes & fees
Aug 4 - Aug 5
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (178)
"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!

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

9.6 out of 10, Exceptional, (13)
"Property was cute ... cleanly and in a great location for what we were looking for. Would definitely recommend to anyone and stay there again ourselves "
The price is CA $181
CA $583 total
includes taxes & fees
Aug 4 - Aug 5
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

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 $132
CA $342 total
includes taxes & fees
Aug 6 - Aug 7
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 $134
CA $461 total
includes taxes & fees
Aug 4 - Aug 5
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

10.0 out of 10, Exceptional, (18)
"Will stay here again "
The price is CA $134
CA $461 total
includes taxes & fees
Aug 4 - Aug 5
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples

10.0 out of 10, Exceptional, (8)
"Great location, friendly and helpful hosts, clean, perfect spot for my solo trip!"
The price is CA $135
CA $407 total
includes taxes & fees
Aug 5 - Aug 6
Scott's Cottage - Truman @ Duval | Perfect Location! Ideal for Solos &Couples

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

10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
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