A sunset over a beach with a wooden pier and a small structure on it.

Cow Key Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Cow Key vacation rentals

House | Exterior

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
$359 nightly
The price is $404
Aug 16 - Aug 17
Total with taxes and fees
Resort View 1BR Suite With Direct Pool Access
Outdoor dining

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.4 out of 10, Exceptional, (173 reviews)
"Great place "
United States
David
Cottage with Pool and Dockage, just minutes to Key West
A heated pool

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.4 out of 10, Exceptional, (114 reviews)
"Excellent stay, great location! "
United States
Dr. Christopher S.
$244 nightly
The price is $271
Jul 20 - Jul 21
Total with taxes and fees
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Terrace/patio

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (43 reviews)
"Great location to Duval and a quiet comfy place to stay"
United States
Brent Y.
$347 nightly
The price is $385
Jul 21 - Jul 22
Total with taxes and fees
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Exterior detail

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (105 reviews)
"Not really close to much but a comfortable bed and clean room. The pool and grounds are lovely. Will stay again but rent a golf cart. "
United States
Laura T.
$296 nightly
The price is $328
Aug 4 - Aug 5
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A heated pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (55 reviews)
"Things ran smoorhly with booking and check-in. "
United States
Bev H.
$326 nightly
The price is $361
Jul 26 - Jul 27
Total with taxes and fees
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Exterior

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (93 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
$388 nightly
The price is $431
Jul 20 - Jul 21
Total with taxes and fees
SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Property grounds

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

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (161 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
$537 nightly
The price is $596
Jul 19 - Jul 20
Total with taxes and fees
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (444 reviews)
"Great location! Close to everything! We biked everywhere and accommodations had everything we needed. "
United States
Richard A.
$215 nightly
The price is $239
Jul 20 - Jul 21
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
Exterior

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (109 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
$639 nightly
The price is $710
Aug 15 - Aug 16
Total with taxes and fees
SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool, a heated pool

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
$617 nightly
The price is $685
Aug 3 - Aug 4
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key
Exterior

Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
9.8 out of 10, Exceptional, (38 reviews)
"Fantastic and cozy… and surprisingly right in the middle of Key West fun"
United States
Jay R.
$328 nightly
The price is $364
Aug 2 - Aug 3
Total with taxes and fees
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Beach

Canal-view 2BR/2BA home with pool, hot tub, and dock access.

Canal-view 2BR/2BA home with pool, hot tub, and dock access.
Cudjoe Key
9.2 out of 10, Wonderful, (30 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
$555 nightly
The price is $616
Jul 26 - Jul 27
Total with taxes and fees
Canal-view 2BR/2BA home with pool, hot tub, and dock access.
Terrace/patio

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

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (148 reviews)
"Nice property in a beautiful location. Great place to sit and enjoy the scenery and activities. "
United States
Andy D.
$849 nightly
The price is $943
Jul 19 - Jul 20
Total with taxes and fees
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Beach towels

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
9.8 out of 10, Exceptional, (45 reviews)
"Great place and location. Walking distance to many shops and restaurants. Our flight arrived a few hours before check in, but the place was ready and we were able to get in right away. Would stay here again! "
United States
Heather W.
$319 nightly
The price is $355
Jul 19 - Jul 20
Total with taxes and fees
STEPS TO DUVAL! OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Exterior detail

Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
Old Town Key West
9.8 out of 10, Exceptional, (27 reviews)
"Awesome location & very helpful host!"
United States
Jay M.
$328 nightly
The price is $364
Aug 2 - Aug 3
Total with taxes and fees
Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West
A heated pool

Chagall's Corner | Newly Remodeled!

Chagall's Corner | Newly Remodeled!
Old Town Key West
9.0 out of 10, Wonderful, (43 reviews)
"Very nice place to stay, close to many attractions. "
United States
Maria B.
$326 nightly
The price is $361
Jul 23 - Jul 24
Total with taxes and fees
Chagall's Corner | Newly Remodeled!
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (192 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
$274 nightly
The price is $308
Jul 17 - Jul 18
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Outdoor pool, a heated pool

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (98 reviews)
"Perfect location. Privacy and comfort."
United States
Anthony
$362 nightly
The price is $401
Aug 1 - Aug 2
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
House | 2 bedrooms

Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
$593 nightly
The price is $667
Aug 16 - Aug 17
Total with taxes and fees
Resort View 2BR Residence
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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Top Cow Key Hotel Reviews

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

8/10 Good
"Room was great, bar and restaurant was excellent especially breakfast! Staff were friendly, not picking but almost no decent shade in the onsite pool and one elevator down, great stay otherwise!"
Paul 3-night trip
Posted 1 hour ago
The Reach Key West, Curio Collection by Hilton

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 $239 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.

Explore a world of travel with Expedia

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?

Sugarloaf Key RV Resort & Cottages: Visitors like this Cow Key vacation home rental. It is located near a metro station and offers an outdoor pool, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

What can I see and do in Cow Key?

Explore the area and family-friendly sights such as Key West Shipwreck Museum, or get out into nature at a spot like Southernmost Point. While in the area, you can also visit popular places like Duval Street and Florida Keys Beaches.

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.