Cow Key Vacation Rentals from $296: Search Short-Term Rentals

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In two weeks

In two months

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Our top choices for Cow Key vacation rentals

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key

David

$346 nightly

Apr 22 - Apr 23

Total with taxes and fees

Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

$975 nightly

Apr 12 - Apr 13

Total with taxes and fees

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key

christopher v.

$449 nightly

Apr 19 - Apr 20

Total with taxes and fees

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

Shayne H.

$449 nightly

Apr 13 - Apr 14

Total with taxes and fees

Spanish Queen @Venture Out, Cudjoe Key

Cudjoe Key

Kimberly G.

$617 nightly

Apr 20 - Apr 21

Total with taxes and fees

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key

Peggy H.

Aqua Lodges at Hurricane Hole Marina

Stock Island

Jordan

$289 nightly

Apr 7 - Apr 8

Total with taxes and fees

Charming cottages, dockage, pool, just minutes to Key West

Cudjoe Key

Laura

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Top Cow Key Hotel Reviews

Havana Cabana at Key West

10/10 Excellent

"The property was friendly with pets. Staff very nice. "

Pier House Resort & Spa

6/10 Okay

"We booked an ocean front room through Expedia. The online pictures versus the actual condition of the room and property were misleading. The room we had (#208) was very dated, water damage in the ceiling, crown molding separated ftom ceiling, base mokding rotten and separated from wall. The overall room condition was clean and housekeeping was very attentive. The general consensus from other guests was they need to update the rooms to reflect the steep prices. Overall the location and stay was nice but doubtful we would stay here again. There are other places with better amenities and cheaper rates. If you plan to use the pool or beach chairs youre going to have to beat the peipke that put towels down at 7 am and take spots all day and not use."

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"We stayed here for one night and had a wonderful experience. The hotel is beautiful and very clean, and the pool area was amazing. The ocean views were incredible and made the stay even more special. Even though it was a short visit, we really enjoyed our time here and will definitely be coming back again!"

Beachside Resort & Residences

4/10 Poor

"Room floors were unswept and so was balcony. Balcony had an entire snack bar on the floor of balcony. I found a watch battery on the floor of the main bathroom. I was with my 13 month old baby. Had he found that and swallowed it we would have a bigger issue at hand. I went to front desk and ask that housekeeping come in and sweep and mop floors in room and balcony. All they did was pick up the granola bar. Room floor still had dry food on floor and our feet were black from walking in room barefooted. Would have mopped floors myself but all that was provided was a broom. Not even a dust pan. No dish soap either. Next issue, toilets barely flushed. Had to report a clogged toilet and the other not flushing at check out. Main bathroom sink faucet was leaking tons of water when turned on. And finally, got room with pool access..DO NOT bother to rent room with that in mind! It’s stairs leading down into a very steep area with bushes etc! Not one paver to even create somewhat of a walk way. Very dangerous and not really a walkable area. I left me kids go down that way first day and when I saw it from the pool I was shocked how they can say that is “accessible”. For the money I paid for 4 nights I was very disappointed. And I will say this… Key West is my hometown and I was visiting family. Next time I’ll just go to a cheaper hotel for the same quality room. Disappointing "

DoubleTree Resort by Hilton Grand Key - Key West

6/10 Okay

"I recently stayed at a DoubleTree Hotel and, unfortunately, the experience fell well below expectations. One of the most noticeable issues was the cleanliness of the property. There was visible garbage around the exterior areas and even near the pool, which made it feel poorly maintained and not very inviting for guests trying to relax. The pool area, in particular, was disappointing. Instead of being a clean, enjoyable space, it appeared neglected, with trash left unattended for extended periods. This really detracted from what should have been a highlight of the stay. Another major concern was the concierge service. I found the staff to be unresponsive and unreliable when assistance was needed. Requests either took far too long to be addressed or were simply not followed through, which made planning activities or resolving small issues unnecessarily frustrating. Overall, this stay did not meet the standard I would expect from a DoubleTree property. I would recommend that management focus on improving cleanliness and staff responsiveness to provide a better experience for future guests. "

Find out more about Cow Key

Everything you need to know about Cow Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cow Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cow Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cow Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cow Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cow Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $296 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cow Key rentals

At Expedia, we put the best Cow Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cow Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cow Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cow Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Cow Key?

Yes, we have vacation rentals near well known local attractions in Cow Key, or you can select a more secluded option if you're looking for relaxation. Cow Key is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

What are some of the best vacation rentals that Cow Key has to offer?

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!: You might want to consider this vacation rental near Cow Key, which is located on the waterfront and has a balcony, a hot tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Cow Key?

Explore the area and family-friendly sights such as Mel Fisher Maritime Museum, or get out into nature at a spot like Key West Tropical Forest and Botanical Garden. In the larger area, you’ll find Duval Street and Stock Island Yacht Club & Marina.

What are vacation rentals like in Cow Key?

Vacation rentals are private accommodations you can stay in for several days or more in Cow Key. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.

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Check prices for these dates

Our top choices for Cow Key vacation rentals

Cottage with Pool and Dockage, just minutes to Key West

Atlantic View Luxury Villa with Pool

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Spanish Queen @Venture Out, Cudjoe Key

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Aqua Lodges at Hurricane Hole Marina

Charming cottages, dockage, pool, just minutes to Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Paradise found

Post Card Point #319 - Ocean Views!

Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise

Living the Dream Key West Style

Grand Marina Suite by Brightwild Waterfront

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Find vacation rentals that suit your style

Top Cow Key Hotel Reviews

Havana Cabana at Key West

Find out more about Cow Key

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