Cow Key Vacation Packages

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Your Cow Key Vacation

When you book a vacation package to Cow Key, you can relax and enjoy your escape knowing that all your travel arrangements have been worked out ahead of time. Uncover the wonders of this lively city from your base in a neighborhood like Sunset Key, which is good for coastal beaches. If your trip to Cow Key includes some sightseeing, check out famous attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Your ideal Cow Key vacation is only clicks away. Explore hotels, flights and more on Expedia for an adventure that's tailored to suit your travel style.

Top Cow Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Creekside Inn
Casablanca Miami Beach
Cavalier Hotel South Beach

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Cow Key Hotel Deals

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $443 per night from Apr 20 to Apr 21
CA $443
CA $587 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,800 reviews)
This Margaritaville has different amenities than others, so our expectations might have been high. We were bummed to learn they do not have pool side or beach service. The pool was small, but they do have a small hot tub, however, it is older and not the best. The room we stayed in was a 2 bedroom ...

Reviewed on Mar 25, 2026

Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $357 per night from Apr 19 to Apr 20
CA $357
CA $479 total
Apr 19 - Apr 20
includes taxes & fees
8.2/10 Very Good! (1,996 reviews)
Check in staff was great!

Reviewed on Mar 25, 2026

Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $388 per night from Apr 13 to Apr 14
CA $388
CA $568 total
Apr 13 - Apr 14
includes taxes & fees
8.6/10 Excellent! (2,086 reviews)
Shuttle times are extremely accurate. Beautfil place with friendly staff. Only wish checkout time was a bit later. Elevators were out our entire stay. We were on third floor. The staff did offer to help carry our luggage up.

Reviewed on Mar 22, 2026

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