Cow Key Holidays

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Top Flight + Hotel Deals in Cow Key

Price found within the past 48 hours. Click for updated prices.
Hilton Cabana Miami Beach Resort

Hilton Cabana Miami Beach Resort

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 23 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (292 reviews)
The hotel has potential, but cleanliness definitely needs improvement. Our bathroom had hair stuck to the ceiling of the shower and visible mold in some areas, which was off-putting. Additionally, the parking fees are excessive. Hilton charged $57 + tax for parking, while a lot just two minutes away on foot offered the same service for only $30. For guests already paying a premium to stay here, the parking costs feel unjustified. I’d strongly recommend lowering the price to be more competitive with the surrounding area.

Reviewed on 30 Jul 2025

The Gabriel Miami South Beach, Curio Collection by Hilton

The Gabriel Miami South Beach, Curio Collection by Hilton

4 out of 5
South Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 23 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (877 reviews)
The property had just gone under new management, and things were a bit hectic. Unfortunately, we didn’t have TV service during our entire stay. However, the manager, Eric, went above and beyond to make up for the inconvenience—providing $15 food vouchers throughout our visit and waiving the resort fees. What a fantastic way to turn things around and keep a guest happy! Superb team and a perfect location. Be sure to go see Eric and his staff—they’re truly amazing individuals!

Reviewed on 31 Jul 2025

Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
per person
24 Oct - 28 Oct
found 23 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,786 reviews)
Quiet ,clean property. Nice stay

Reviewed on 31 Jul 2025

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 23 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,099 reviews)
Everything was good however same breakfast choices everyday.

Reviewed on 20 Jul 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 23 hours ago
Return flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (6,535 reviews)
They charge a parking fee of 72 dlrs per day plu some additional hotel fees and taxes..so even though you paid your bill theough expedia you still have to pay money ehen checking out. Also pool hours are ridiculous...kid pool closes at 6:30 and i got there at 6 and they eere already closing, next day i got there at 5:45 and they were closed too! So my toddler did not enhoy the slide...they do not have a set time and thaeybtake you out. Crazy! We got this hotel because of the pool

Reviewed on 1 Aug 2025

Top hotels in Cow Key

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 €177 per night from 18 Aug to 19 Aug
€177
18 Aug - 19 Aug
includes taxes & fees
8.4/10 Very Good! (1,397 reviews)
"Loved the room! So big and spacious. The room we had 123 had stainless steel pans and not many, basically impossible to cook with and not burn. Everything else was awesome. Call in plenty of time if you need ice. Pool was awesome and opened 24/7."

Reviewed on 28 Jul 2025

Beachside Resort & Residences
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is €241 per night from 25 Aug to 26 Aug
€241
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (2,661 reviews)
"Great view from the room and quiet location on the property."

Reviewed on 29 Jul 2025

Southernmost Beach Resort and Guesthouses
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 €169 per night from 1 Sept to 2 Sept
€169
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,499 reviews)
"Staff was great, really enjoyed our short stay."

Reviewed on 31 Jul 2025

Blue Flamingo Resort Key West
See all 3,136 properties in Cow Key
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.

Frequently asked questions

How much does a Cow Key holiday package cost?
Offering great value package deals from €354 on Expedia, you'll be pleasantly surprised at how much a holiday to Cow Key costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Cow Key?
You're likely to find reduced prices and greater availability in January, February and August. Take a look at our cheap Cow Key holiday packages and you could score some excellent off-season deals.
How many days is enough for Cow Key?
Generally, a handful of days is enough to tick off the major sights during your Cow Key holiday. But if you prefer to have some time to rest or take day tours, consider extending your itinerary.
How to find the best Cow Key package deals?
Use Expedia's filters to help you find some unbeatable Cow Key package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Cow Key package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Cow Key holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and stays individually. Better still, you can customise your Cow Key escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Cow Key?
If you've got your Cow Key travel dates confirmed, book as soon as you can to score some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Cow Key?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Cow Key.
  2. Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodation will likely be the biggest expense during your trip to Cow Key.
  3. Decide how long to go for: Now that you know more about Cow Key, you can work out the ideal length of your break. Create a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customised Cow Key holiday package.

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