Stock Island Beach Vacations
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Top Beach vacation packages in Stock Island
Price found within the past 48 hours. Click for updated prices.
- The Perry Hotel & Marina Key West
Sep 11 - Sep 14The Perry Hotel & Marina Key West + Flight
Stock Island3 nights4.0 star property9.4/10 - Exceptional (1,290 reviews)"This place is AMAZING, everything was perfect. Cleanness, staff, location, outstanding!!"Reviewed July 16, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$730$573found 2 days agoper traveler - Coconut Beach Resort
Sep 18 - Sep 24Coconut Beach Resort + Flight
Old Town Key West6 nights2.5 star property8.8/10 - Excellent (208 reviews)"So overall its a nice spot but the units are split with a dividing door, so when we arrived to check out the room the doors were not locked and people were in our unit. For it being an ocean view with a premium price, the resort description said they have someone who frequently cleans the beach access from debris but it was completely covered in sargasim seaweed with no access to the water. Make sure you check the sargasim season because it very much limits your access to the beach. On our..."Reviewed July 15, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - Ibis Bay Beach Resort
Sep 11 - Sep 14Ibis Bay Beach Resort + Flight
Northside Resort3 nights2.5 star property8.2/10 - Very Good (2,284 reviews)Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$798$582found 2 days agoper traveler - Pier House Resort & Spa
Aug 27 - Aug 31Pier House Resort & Spa + Flight
Key West Historic District4 nights4.0 star property9.0/10 - Wonderful (1,225 reviews)"The first day we arrived. I let the front desk know the lights in the bathroom. We’re not working. The coffee maker was not working for me and the phone did not work. When I tried to communicate with the front desk over the phone. They acted like I was prank, calling them, and that it was my fault that the phone wasn’t working. They never did fix the lighting in the bathroom. I had zero lighting to put make up on the floors were always dirty. They didn’t clean the room until after three, when I..."Reviewed July 16, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$1,234$911found 1 day agoper traveler - Hyatt Vacation Club at Beach House, Key West
Oct 3 - Oct 8Hyatt Vacation Club at Beach House, Key West + Flight
Key West5 nights3.5 star property9.4/10 - Exceptional (1,153 reviews)"Fue una muy buena experiencia, muy limpio todo ."Reviewed July 15, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$1,645$1,281found 1 day agoper traveler
Discover the most popular places to visit in Stock Island
What to do in Stock Island
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
96% of travelers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
$69
per adult
88% of travelers recommend
Shipwreck Treasure Museum Tickets
$19
per adult
80% of travelers recommend
Top Beach Stock Island Hotels
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West4.0 star property
Stock Island, 0.5 mi from Stock Island
9.4 out of 10, Exceptional, (1,290 reviews)
9.4/10
Exceptional
(1,290 reviews)
"This place is AMAZING, everything was perfect.
Cleanness, staff, location, outstanding!!"
$192 nightly
The price is $216
$216 total
Jul 26 - Jul 27
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole Marina2.0 star property
Stock Island, 0.4 mi from Stock Island
8.8 out of 10, Excellent, (192 reviews)
8.8/10
Excellent
(192 reviews)
"This is non luxury working marina. Real life experience. Loved it."
$265 nightly
The price is $298
$298 total
Jul 21 - Jul 22
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
47ft Viking Yacht · 2 Pools · Perry Marina · Key WestStock Island, 0.6 mi from Stock Island
7.6 out of 10, Good, (39 reviews)
7.6/10
Good
(39 reviews)
$372 nightly
The price is $413
$413 total
Aug 3 - Aug 4
Total with taxes and fees
Cozy Houseboat
Cozy HouseboatStock Island, 0.5 mi from Stock Island
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
$434 nightly
The price is $482
$482 total
Jul 20 - Jul 21
Total with taxes and fees
Eddie Griffiths Overnight Charters and Vacation Rentals!!!!!
Eddie Griffiths Overnight Charters and Vacation Rentals!!!!!Stock Island, 0.6 mi from Stock Island
9.4 out of 10, Exceptional, (43 reviews)
9.4/10
Exceptional
(43 reviews)
"This place was awesome. AND HAS A HEATED SHOWER!!!!! Capt was super responsive and helpful! "
$343 nightly
The price is $381
$381 total
Jul 27 - Jul 28
Total with taxes and fees
Living the Dream Key West Style
Living the Dream Key West StyleStock Island, 0.6 mi from Stock Island
10.0 out of 10, Exceptional, (61 reviews)
10/10
Exceptional
(61 reviews)
"Friendly host and unique location"
$480 nightly
The price is $533
$533 total
Jul 22 - Jul 23
Total with taxes and fees
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & ParkingStock Island, 0.2 mi from Stock Island
10.0 out of 10, Exceptional, (23 reviews)
10/10
Exceptional
(23 reviews)
$899 nightly
The price is $998
$998 total
Jul 21 - Jul 22
Total with taxes and fees
Gone Coastal
Gone CoastalStock Island, 0.1 mi from Stock Island
9.6 out of 10, Exceptional, (22 reviews)
9.6/10
Exceptional
(22 reviews)
"We didn’t cook… but there were dishes and silverware, pots and pans. There is not a dishwasher and not a lot of glasses. It was clean and functional."
$550 nightly
The price is $611
$611 total
Aug 16 - Aug 17
Total with taxes and fees
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.
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.
Find your perfect Stock Island beach vacation
How do I book the best Stock Island beach vacation packages?
Life’s a beach when you dive into our brilliant Stock Island beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.
How can I find cheap beach vacations in Stock Island?
A rental steps from the shore creates an amazingly affordable Stock Island beach vacation. Seaside sojourns during low season start from $573. Prices and availability are subject to change. Additional terms may apply.
How can I book the best family beach vacations in Stock Island?
With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.
How do I find a Stock Island beachfront vacation?
Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.
Can I book a package including a Stock Island vacation beach house rental?
Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.
Can I find Stock Island beach vacation deals?
Sort your search results by deals to delight in amazing Stock Island beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.
Can I book a Stock Island beach trip with free cancellation and/or flexible dates?
Just like the Stock Island tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.
Why should I book my Stock Island beach vacation with Expedia?
Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Stock Island. (OK, maybe not that last part.)