Stock Island Adults Only Vacations

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Flight and Adults Only hotel deals in Stock Island

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

Old Town Key West
CA $1,654
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (1,397 reviews)
Two concerns: 1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result. 2) concern may be equal parts Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, etc. show up at check-in/out. Just quote the customer the true cost of their stay and avoid creating a frustration on behalf of the consumer.

Reviewed on Sep 1, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
CA $3,429
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,005 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $3,122
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
8.8/10 Excellent! (3,534 reviews)
The resort fee is very expensive for what the resort has to offer for the guests. I will not rebook this resort the next time we are in Keywest. No shuttle services are offered. Nothing complimentary but two welcome drinks.

Reviewed on Sep 1, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
CA $2,801
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (1,027 reviews)
Beautiful stay

Reviewed on Aug 31, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,584
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
We were on the top floor. Lots of stairs. Make sure you can do stairs when booking or request a lower floor. It's beautiful, great location and would go back again.

Reviewed on Sep 1, 2026

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3 Night Adults Only holidays in Stock Island

Price found within the past 48 hours. Click for updated prices.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

Old Town Key West
CA $671
per person
Nov 9 - Nov 12
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,397 reviews)
Two concerns: 1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result. 2) concern may be equal parts Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, etc. show up at check-in/out. Just quote the customer the true cost of their stay and avoid creating a frustration on behalf of the consumer.

Reviewed on Sep 1, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
CA $1,221
per person
Nov 9 - Nov 12
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
9.2/10 Wonderful! (1,027 reviews)
Beautiful stay

Reviewed on Aug 31, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $1,055
per person
Nov 9 - Nov 12
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Key West (EYW)
8.8/10 Excellent! (3,534 reviews)
The resort fee is very expensive for what the resort has to offer for the guests. I will not rebook this resort the next time we are in Keywest. No shuttle services are offered. Nothing complimentary but two welcome drinks.

Reviewed on Sep 1, 2026

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4 Night Adults Only holidays in Stock Island

Price found within the past 48 hours. Click for updated prices.
Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

Old Town Key West
CA $1,473
per person
Nov 11 - Nov 15
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
9.4/10 Exceptional! (494 reviews)
It is located in the heart of he old district snd everything was so accessible without having to use our car. The property is only 1 block off Duval so,we had the advantage of,accessibility without the noise. The property is protected by foliage which makes it feel private and protected. The complimentary breakfast is lovely, and there is wine by the pool daily. Dwight welcomes guests upon arrival,and made us feel,at home. The beds are so comfy, and each cottage has its own flavor. I hope to return and stay at Ella’s Cottages again, Expedia does a great job helping us narrow down our priorities, amenities, location, etc. That enabled us to find Ella’s Cottages, which was perfect for us.

Reviewed on Sep 1, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,307
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
We were on the top floor. Lots of stairs. Make sure you can do stairs when booking or request a lower floor. It's beautiful, great location and would go back again.

Reviewed on Sep 1, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
CA $4,698
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

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Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $59
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $77
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

CA $109
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
See all activities in Stock Island

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.