Holiday Homes in Stock Island

    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
In one month
In two months

Featured Holiday Homes in Stock Island

Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West

The price is AU$695
includes taxes & fees
23 Aug - 24 Aug
Charming 1-Bedroom, 1-Beth Sailboat in wonderful Key West

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

9.8 out of 10, Exceptional, (112)
"Very comfortable house in a great location. "
The price is AU$838
includes taxes & fees
18 Aug - 19 Aug
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Docked in Paradise

The price is AU$673
includes taxes & fees
23 Aug - 24 Aug
Docked in Paradise

FREE TIME 50’ 2 Cabin Yacht Key West

The price is AU$841
includes taxes & fees
25 Aug - 26 Aug
FREE TIME 50’ 2 Cabin Yacht Key West

Gone Coastal

9.8 out of 10, Exceptional, (17)
"Loved this property- walking distance to some lovely restaurants and bars, especially around the marina which is only 15 mins walk away! The property is well equipped and has a choice of great balconies/terraces and the development is very quiet - pool area was great too. Highly recommend this place and we loved Key West."
Gone Coastal

Grand Admiral - 46’ 2 Cabin Yacht

The price is AU$1,361
includes taxes & fees
30 Aug - 31 Aug
Grand Admiral - 46’ 2 Cabin Yacht

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (118)
"Clean property in a nice location."
The price is AU$809
includes taxes & fees
2 Sept - 3 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

9.8 out of 10, Exceptional, (8)
"Beautiful place!"
The price is AU$1,275
includes taxes & fees
22 Aug - 23 Aug
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

9.8 out of 10, Exceptional, (142)
"Very clean cottage right on the corner of the harbor and the canal. Wonderful views!"
The price is AU$1,379
includes taxes & fees
18 Aug - 19 Aug
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

2.0 star property
9.0 out of 10, Wonderful, (7)
"Loved the location! Very nice park. Our place had an amazing view to watch the sunrise and to enjoy a nice home cooked meal before heading up to the pool."
The price is AU$966
includes taxes & fees
2 Sept - 3 Sept
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Post Card Point #319 - Ocean Views!

10.0 out of 10, Exceptional, (48)
"Really nice super clean & modern house with a great view. Lots of space. The community it’s in was very nice and quiet."
The price is AU$1,225
includes taxes & fees
2 Sept - 3 Sept
Post Card Point #319 - Ocean Views!

Galleon Getaway #533- Oceanfront Community

The price is AU$841
includes taxes & fees
30 Aug - 31 Aug
Galleon Getaway #533- Oceanfront Community

Reel Island Retreat #273 at Venture Out in the Florida Keys

9.6 out of 10, Exceptional, (7)
"The staff at Venture one was absolutely amazing. The home we stayed in was also a great location. Dated but clean. Definitely will stay at Venture again !"
The price is AU$1,018
includes taxes & fees
31 Aug - 1 Sept
Reel Island Retreat #273 at Venture Out in the Florida Keys

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

10.0 out of 10, Exceptional, (1)
"Beautiful "
The price is AU$1,653
includes taxes & fees
30 Aug - 31 Aug
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (96)
"Good location, short drive to lots of activities. Had to leave a day early due to family crises, but had a great two nights there. Thanks!!"
The price is AU$678
includes taxes & fees
28 Aug - 29 Aug
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is AU$924
includes taxes & fees
18 Aug - 19 Aug
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

The price is AU$902
includes taxes & fees
31 Aug - 1 Sept
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

9.4 out of 10, Exceptional, (19)
"We enjoyed our stay at venture out at the Spanish main residence it was lovely and we are going to return again next year"
The price is AU$1,114
includes taxes & fees
30 Aug - 31 Aug
Spanish Queen @Venture Out, Cudjoe Key

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (81)
"Great location near Key West. Awesome property, will book again."
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

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

10.0 out of 10, Exceptional, (1)
"We just needed a place to sleep for a few days while visiting friends on Big Pine. The house had what we needed. The home and furnishings were quite dated with some rust stains on the air vents and in the bath but if you're not picky about that, then this is a great place. The main areas were clean, although there was dirt and dust behind the night stands (needed to access the outlet so had to look there). We didn't use any of the amenities but still had to pay 130 extra when we checked in at...
The price is AU$689
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
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