Stock Island Holiday Rentals

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Holiday Rentals in Stock Island

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (104)
"Nice for affordable price "
The price is AU$427
includes taxes & fees
26 Nov - 27 Nov
Aqua Lodges at Hurricane Hole Marina

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

10.0 out of 10, Exceptional, (14)
"BOOK THIS BOAT!!!’ TOP 10 vacations ever!!! Hannah was so accommodating and onboarded us to The Grand Admiral. Beautiful marina with easy access to The Perry hotel and bar, making it a very very comfortable stay. And then the excursion 😍!! Captain Jeff made our day exceptional. We encountered dolphins, lounged on the sandbar, and grilled while watching a breathtaking sunset. We will be making this an annual trip! Thank you Captain Jeff for the best day ever."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

Luxury 62' Yacht! In a Beautiful Resort

10.0 out of 10, Exceptional, (7)
"Excellent boat, excellent stay. Would love to return."
Luxury 62' Yacht! In a Beautiful Resort

5 star resort living w/ pool! Family sized w/ full kitchen & great views!

7.4 out of 10, Good, (9)
"Can’t beat staying on a boat and taking it for a spin while you’re on vacation! Host, captain and crew were all great!"
The price is AU$887
includes taxes & fees
19 Dec - 20 Dec
5 star resort living w/ pool! Family sized w/ full kitchen & great views!

LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!

9.8 out of 10, Exceptional, (78)
"Don't overthink it - just do it and the rewards will follow - Boat - well cared for Marina - very well appointed Hotel - fantastic - Stuttle helped make it easier to get to town You are off the beaten path of the craziness of Duval which is both nice and frustrating depending on your vision for the time there - RECOMMEND the boat out for the over night worth every penny! "
LAST MINUTE DISCOUNT! 48' Yacht located in a Beautiful Resort!

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

9.0 out of 10, Wonderful, (30)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach

10.0 out of 10, Exceptional, (232)
"House was very clean and nicely decorated. The house was centrally located to all Key West activities. Host was also very responsive. "
Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach

NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

9.6 out of 10, Exceptional, (194)
"Overall we had a fabulous stay. The space was perfect for our six adults and two kids, the AC blew cold for relief from summer heat, and there were plenty of delicious food options nearby. My family thanked me multiple times for the great find. We would definitely stay there again!"
NEWLY REMODELED KITCHEN!! PET FRIENDLY! 3 Bedroom 3 bathroom home. Sleeps 8

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (356)
"We walked most everywhere and loved the Southernmost Beach Bar! Eating at Moon Dog Cafe was so spectacular that we ate there 3 times in 2 days! This place is all it says it is. Simply perfect. "
The price is AU$371
includes taxes & fees
2 Dec - 3 Dec
Steps from Duval, Pool on Site & Bikes Included!

Poolside Cottage #411

10.0 out of 10, Exceptional, (30)
"Nice location very close to everything and close enough to Duval St. Unit itself was in good condition and the kitchen stocked pretty good but was missing dish cloths, dish towels and dishwasher detergent. None of the grills on the property were functional. Host was very responsive the entire process. Would stay there again"
The price is AU$592
includes taxes & fees
2 Dec - 3 Dec
Poolside Cottage #411

34’ Catamaran Sailboat

9.6 out of 10, Exceptional, (27)
"Overall it was a great experience."
34’ Catamaran Sailboat

TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

9.2 out of 10, Wonderful, (165)
"We found the tides on Simonton online and booked it immediately. When we arrived, the check-in process was very easy and the location is very nice. We ate down the street at Duffys twice during our stay and it is an amazing place. I highly recommend their prime rib. we will definitely be back "
TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (214)
"Very clean. Could use some updating such as fresh paint. "
The price is AU$679
includes taxes & fees
26 Nov - 27 Nov
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

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

9.0 out of 10, Wonderful, (202)
"Close to Duval Street and within walking distance to everything. Full kitchen is nice. Good for a Key West visit. "
The price is AU$428
includes taxes & fees
11 Dec - 12 Dec
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

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

9.4 out of 10, Exceptional, (112)
"Quit little place."
The price is AU$485
includes taxes & fees
26 Nov - 27 Nov
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

9.2 out of 10, Wonderful, (238)
"Place was very comfortable-great for couples who "
The price is AU$906
includes taxes & fees
27 Nov - 28 Nov
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (184)
"Loved this ocean view property! Very nice location and very comfortable home!"
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Heart of Old Town getaway, perfect romantic retreat - near the action

9.0 out of 10, Wonderful, (38)
"Good"
The price is AU$552
includes taxes & fees
3 Dec - 4 Dec
Heart of Old Town getaway, perfect romantic retreat - near the action

Feb 3-10 $245 off the rates close beach full kitchen & patio

9.6 out of 10, Exceptional, (200)
"Very walkable. Cozy comfortable place. Cute and safe neighborhood. Setup well for cooking. AC pumps some good cold air. "
Feb 3-10 $245 off the rates close beach full kitchen & patio

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (216)
"Property was clean and had everything to have an enjoyable stay."
The price is AU$1,115
includes taxes & fees
26 Nov - 27 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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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Other types of properties in Stock Island you may be interested in

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
8.8 out of 10, Excellent, (1520)
"Beautiful facility with gorgeous view"
The price is AU$400
includes taxes & fees
1 Dec - 2 Dec
Oceans Edge Key West Resort, Hotel & Marina

The Perry Hotel & Marina Key West

4.0 star property
9.4 out of 10, Exceptional, (1003)
"Beautiful meal at the restaurant"
The price is AU$338
includes taxes & fees
15 Dec - 16 Dec
The Perry Hotel & Marina Key West

Southernmost Beach Resort

4.0 star property
8.6 out of 10, Excellent, (2191)
"Beautiful property! Loved our stay and the staff were wonderful. "
The price is AU$525
includes taxes & fees
17 Dec - 18 Dec
Southernmost Beach Resort
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.