Holiday Rentals in Cow Key

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Holiday Rentals in Cow Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (112)
"We loved staying on the houseboat."
The price is €280
includes taxes & fees
22 Jan - 23 Jan
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (361)
"Fun little place with a great pool. Ken was very helpful in all aspects. Highly recommended. Be aware its a small place but very comfortable."
The price is €335
includes taxes & fees
9 Feb - 10 Feb
Steps from Duval, Pool on Site & Bikes Included!

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (30)
"It was 6 miles from key west which we liked. It sits in an inlet so you don’t see much ocean or beach. Property had a separate bath house. Bathroom wasn’t really usable & tv cord was missing so no tv (wasn’t there to watch tv) If you have problems with close spaces, it wouldn’t be for you "
34’ Catamaran Sailboat

Poolside Cottage #411

10.0 out of 10, Exceptional, (36)
"Great little condo - perfect for our family to visit Key West! "
The price is €398
includes taxes & fees
28 Jan - 29 Jan
Poolside Cottage #411

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

9.8 out of 10, Exceptional, (16)
"Staying on the Grand Admiral was really awesome for my wife and I. The location at Perry Marina was exceptional. The whole process was very easy, working with Kathy for booking, Stephanie for check-in and Captain John for our charter, everything went smooth. "
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!

9.6 out of 10, Exceptional, (118)
"We had a great time. Enjoyed the property very much."
The price is €658
includes taxes & fees
10 Feb - 11 Feb
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!

FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!

9.4 out of 10, Exceptional, (111)
"Great location!"
The price is €397
includes taxes & fees
29 Jan - 30 Jan
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

8.8 out of 10, Excellent, (205)
"I recently stayed at this property and had a generally pleasant experience. The property itself is nice and well-maintained, with a great location that adds to its appeal. The surrounding area is excellent, making it convenient and enjoyable. However, there were a few downsides to my stay. The internet was not working, which was quite inconvenient. Additionally, while the property is good overall, it could benefit from having a few more amenities. The bathroom, in particular, could use some...
The price is €534
includes taxes & fees
20 Feb - 21 Feb
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

The Caroline Suite | 1 bed, 1 bath condo w/shared pool

9.4 out of 10, Exceptional, (12)
"Place was clear, ready, and in a great area. If your looking for a good place in key west this is it"
The price is €683
includes taxes & fees
23 Jan - 24 Jan
The Caroline Suite | 1 bed, 1 bath condo w/shared pool

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (215)
"Very clean. Could use some updating such as fresh paint. "
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

9.8 out of 10, Exceptional, (117)
"This has been our go to place to stay while in the keys. We love the pool, hot tub and beach. My boys can walk right out into the beach and start fishing. It is out of the hustle and bustle but not too far out. Highly recommend!"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

The Crystalmarine Suite – Rustic Luxury on the Sea

10.0 out of 10, Exceptional, (2)
"This VRBO is a dream for those looking to escape the hustle and bustle of everyday life. With its unique location, it provides a perfect blend of adventure and relaxation. Whether you're looking to reconnect with nature or simply unwind in a beautiful setting, this floating house offers an unparalleled experience."
The price is €878
includes taxes & fees
23 Jan - 24 Jan
The Crystalmarine Suite – Rustic Luxury on the Sea

Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

9.6 out of 10, Exceptional, (82)
"Great trip with 16 people for a 50th birthday party. Host was very helpful and informative throughout the trip. Great for large groups."
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (220)
"Our family loved everything about our stay in Cudjoe Key. The property had everything we needed and was extremely comfortable. The property owner was very friendly and helpful and easy to get a hold of. We highly recommend this place for your next vacation!"
The price is €747
includes taxes & fees
22 Jan - 23 Jan
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

9.0 out of 10, Wonderful, (33)
"It was just the right place for my family. We really enjoyed the view and close proximity to Key West. "
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

GATED OCEANFRONT CONDO AT SMATHER'S BEACH

9.4 out of 10, Exceptional, (118)
"Good location for us. 2 mile walk to Duval St. uber easily accessible. Grocery Store, sandwich shop, Mexican restaurant, and sports bar a few blocks away. Check in required us to go to different location to pick up keys. A negative for us. Also air conditioner would not cool below 78 degrees last 2 nights. Beautiful property we enjoyed "
GATED OCEANFRONT CONDO AT SMATHER'S BEACH

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

9.2 out of 10, Wonderful, (243)
"You cannot beat the location of this property 5 minutes stroll off Duvall. The rooms were clean and well appointed. I was suprised at the small size of the bathrooms the wet shower set up was also a surprise. The orice was good for K.W. I would stay here again."
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Bahama Village studio @ the Galleria!

9.6 out of 10, Exceptional, (10)
"Everything was as advertised. Its location was fantastic with easy access on foot to everything Key West has to offer. Only negative is that there is a high top table and two chairs in a space that really doesn’t afford those niceties. The bed was comfortable. The ac was a bit loud."
Bahama Village studio @ the Galleria!

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (280)
"We had a wonderful week during the Christmas/ New Year break. The condo is exceptional. Very clean including many items that make your stay easy and welcoming. The kitchen is fully stocked, not that one needs much while staying on the island. We relaxed in the condo, enjoyed restaurants and music across the island. "
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

Feb 3-10 $245 off the rates close beach full kitchen & patio

9.6 out of 10, Exceptional, (208)
"We always stay at this location when available. There’s another one at the rear of the property and it was a good spot but we’re spoiled by this one. We’ve stayed here so much it is almost like a second home. It’s well appointed, the shower is huge and the place is cozy and has the lived in feel to it. There’s plenty of basics in the kitchen, full size fridge and stove, the bed is outstanding and adjustable, and there’s even beach chairs to use while staying. Marilyn is a great host and super...
Feb 3-10 $245 off the rates close beach full kitchen & patio
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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Other types of properties in Cow Key you may be interested in

Ibis Bay Beach Resort

2.5 star property
8.0 out of 10, Very good, (1718)
"This place was quite a surprise. We were in the back building by the water, and it was very quiet. Unlike many of the other places which were on the other side of the four-lane highway, this place was removed far enough that you did not hear any traffic. The breakfast was quite good and many options to choose from. The grounds are meticulous. Some of the reviews mentioned, loud air conditioners, and we did not find that to be the case at all. I would come back here in a heartbeat."
The price is €259
includes taxes & fees
22 Jan - 23 Jan
Ibis Bay Beach Resort

Havana Cabana at Key West - Adults Only

4.0 star property
8.8 out of 10, Excellent, (1651)
"The cleanliness and activities around the pool area."
The price is €299
includes taxes & fees
26 Jan - 27 Jan
Havana Cabana at Key West - Adults Only

The Perry Hotel & Marina Key West

4.0 star property
9.4 out of 10, Exceptional, (1007)
"Beautiful views of the harbour from the balcony. Decor of the room was modern industrial look that gives you the feel of a high-end hotel feel. Room had great amenities like plug points next to the bed & USB plug in lamp shade, good coffee machine, mini fridge, ironing board, umbrella etc Nice bath robes and complementary bathroom products, including shower cap. Towels were clean and soft. Bed was huge and comfortable. Good air-conditioning & it wasn’t noisy. Not much around the area but you...
The price is €340
includes taxes & fees
27 Jan - 28 Jan
The Perry Hotel & Marina Key West
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

Are there holiday rentals in Cow Key?

Yes, there are holiday rentals close to the most popular sights in Cow Key, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Cow Key has to offer?

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!: This holiday home rental outside of Cow Key is located on the waterfront, and has a balcony, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 wider area, you’ll find Stock Island Yacht Club & Marina and Key West Golf Club.

What are holiday rentals like in Cow Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cow Key. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips or small group gatherings.