Stock Island Vacation Packages for 2026
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Stock Island Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Ella's Cottages - Key West Historic Inns
Old Town Key West
$1,121
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Clean room, comfortable bed, friendly staff, good amenities!
Reviewed on Oct 20, 2026
The Key West Hotel
Key West Historic District
$1,770
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
Property was everything as described, clean, in the heart of the excitement that is Key West
Pool was refreshing and close to tiki bar and local entertainment.
The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w
May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine
Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity
Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator
We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer
Reviewed on Oct 6, 2026
The Marker Key West Harbor Resort
Key West Historic District
$1,159
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Very clean hotel. Room was spacious and well decorated. Including bathroom. The hotel is situated in a great location.
Reviewed on Oct 23, 2026
Pier House Resort & Spa
Key West Historic District
$1,695
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Wonderful vacation. Pier House is the only resort that I’ll stay at. I have been staying there for years. Everything about it is perfect.
Reviewed on Oct 23, 2026
The Gardens Hotel
Old Town Key West
$2,369
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto
Reviewed on Oct 20, 2026
The Fairhaven House at Solaire Lunara Bay
$9,327
per person
Jan 10 - Jan 14
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free breakfast, free parking, and a fitness center. Popular attractions Duval Street and Smathers Beach are located nearby.
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See all available trips from Columbus to Stock Island
View all tripsStock Island Vacation Packages
Trying to save some money and some time on your upcoming vacation to Stock Island? Well, AARP Travel Center Powered by Expedia® is here to help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Stock Island the best one yet. In just a few clicks, you can select the best Stock Island vacation package for you. We have a huge selection of accommodations and flight, as well as Stock Island things to do to pick from.
Hotels in Stock Island
Our listings include accommodations that are close to all the Stock Island points of interest, and others that are just outside the city center for a quieter retreat.
We have great deals on everything from family-friendly resorts that check off all the vacation must-haves to affordable accommodations perfect for those on wanting to save a little money. You can scan our vast catalog of possibilities and choose the hotel that is ideal for you. With AARP Travel Center's Stock Island hotel packages, you not only get a great rate on your flight, but also a fantastic place to stay.
Things to do in Stock Island
Stock Island is the perfect town when you want to a break from it all. With only around 4,153 people in the city, this quaint town is great for a quite vacation.
If you need more suggestions, then make sure to click on AARP's "Things to Do" tab.
Book Together and Save
As an AARP Member, you can benefit from all the great deals. You can save on select hotels worldwide, flights, and even rental cars. No matter what vacation package you pick, your membership savings helps you get a great deal. The hardest packing you'll have to do is for your suitcase. Book now and get ready for your Stock Island vacation.
Top Hotel Deals
Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Aqua Lodges at Hurricane Hole Marina
5130 Overseas Hwy Key West FL
Stay at this houseboat in Key West. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Duval ...
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Ibis Bay Beach Resort
3101 N. Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. ...
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and Southernmost ...
DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Book a stay at this spa hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in ...
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. ...
The Southernmost Inn - Adults Only
525 United Street Key West FL
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3852 North Roosevelt Boulevard Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the pool ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Feb 3 - Wed, Feb 10
TPA
Tampa Intl.
EYW
Key West Intl.
$107
Roundtrip
found 4 days ago
Mon, Feb 1 - Tue, Mar 2
ORD
O'Hare Intl.
EYW
Key West Intl.
$293
Roundtrip
found 4 days ago
Mon, Feb 1 - Tue, Mar 2
ORD
O'Hare Intl.
EYW
Key West Intl.
$313
Roundtrip
found 4 days ago
Sun, Nov 29 - Thu, Dec 17
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$359
Roundtrip
found 4 days ago
Sun, Jan 17 - Sat, Jan 23
BOS
Logan Intl.
EYW
Key West Intl.
$487
Roundtrip
found 19 hours ago
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All accommodation types in Stock Island
More Types of Hotels
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- Hotels with smoking rooms in Stock Island
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