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, (120)
"Pros: clean, comfortable bed, nice location if you want to be a little outside the main touristy area. Cons: a little pricey for the space $500 on night 2/22"
The price is €375
includes taxes & fees
6 Mar - 7 Mar
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (373)
"The location was perfect! It was 2 or 3 blocks from Duval Street. The bed was comfortable and the room with bath clean."
Steps from Duval, Pool on Site & Bikes Included!

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (804)
"Great place overall and would definitely come back. Only major complaint is they don’t exchange towels. Apparently and old Covid policy that has never been reversed. Kind of annoying when you are staying for a full week and have to go to the laundromat to wash your own towels. But they did offer us late checkout at 11am vs 10am, so that was nice. "
Coconut Mallory Resort And Marina By Kees Vacations

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (289)
"I had a great experience with my family!"
The price is €444
includes taxes & fees
1 Apr - 2 Apr
Hyatt Vacation Club at Sunset Harbor, Key West

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (119)
"This cottage was amazing for so many different reasons. Location, quiet, and detail to guests needs. Marcela was a great communicator. No need to communicate too much, everything worked great! We are returning next year!"
Heart of Downtown Key West Cottage With Off-Street Parking

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

9.6 out of 10, Exceptional, (209)
"Had enjoyable three day visit in Key West. Stayed in comfortable little VRBO house apartment in southern part of Old Town. "
Feb 3-10 $245 off the rates close beach full kitchen & patio

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (195)
"Lovely two bedroom waterfront property is reminiscent of a beachfront cottage in New England or the Outer Banks. If you're expecting a Marriott timeshare on an expensive island in the Caribbean as some of the previous reviews seemed to be then then perhaps look elsewhere. But if you want a comfortable winter escape in an absolutely perfect location both within the resort as well as where it is in the Keys then this is for you. We enjoyed the beautiful view from both the upper deck as well as...
The price is €519
includes taxes & fees
6 Mar - 7 Mar
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

10.0 out of 10, Exceptional, (3)
"I didn’t really know what I was getting into, but I’m glad I didn’t cancel. This was such a beautiful experience to have shared with just myself. The bed was comfortable and I slept really well both nights. The second night, I had to rent a kayak from the marina (40) to get to the house. It was a beautiful sunset paddle. It’s easy enough, but even as an experienced paddler, it’s about 20 minutes . I had to leave around 5am to catch my flight and paddled back to the marina in pitch black. It was...
The price is €327
includes taxes & fees
19 Mar - 20 Mar
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

9.0 out of 10, Wonderful, (157)
"The good: convenient location, quiet, bed was comfortable, the little patio in the back is nice. The bad: there is no “on site’ parking but we always found parking on the street about a block away, The communication with property manager was a bit strange, she accused us of still being inside the unit a full day after we had check out on time, despite texting her to tell her we had left (an hour before check out)"
Spec.Feb.24-Mar 1 @229+ w. 3 night stay close beach

Resort View 1BR Suite

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is €626
includes taxes & fees
1 Apr - 2 Apr
Resort View 1BR Suite

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

9.2 out of 10, Wonderful, (253)
"A great place. We stayed for a long weekend and it was perfect. Easy communication and wonderful place. Bathrooms are a touch small if you’re a big guy but the rest is the best. Looking forward to coming back."
The price is €608
includes taxes & fees
4 Mar - 5 Mar
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

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

9.8 out of 10, Exceptional, (281)
"Most impressive condo and grounds - heated pool and huge hot tub and very friendly people! This condo had the best information/directions (and even labeled lightswitches) of anywhere we have ever stayed!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

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

8.6 out of 10, Excellent, (107)
"Drove From CLE to The Keys with my dog and enjoyed the quietness of the property. 30 an hour from Key West. Great rate. Would recommend. "
The price is €408
includes taxes & fees
14 Mar - 15 Mar
Charming cottages, dockage, pool, just minutes to Key West

Poolside Cottage #411

9.8 out of 10, Exceptional, (38)
"Quiet area close to everything we were looking for. "
The price is €515
includes taxes & fees
3 Mar - 4 Mar
Poolside Cottage #411

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

10.0 out of 10, Exceptional, (4)
"Was just a teaser initial trip to Key West but staying on the water was awesome! Beautiful views and great amenities. Kevin and Captain Philip were great throughout the whole process including great local recommendations! One thing to note, if you are 6’ plus, will need to watch your head and the steps downstairs require concentration. As a shorter person (barely 5’!) it all worked perfectly for me! Look forward to staying again and taking the boat out next time! "
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

The Cozy Little Cottage!

9.6 out of 10, Exceptional, (21)
"The cottage was so quaint! The location couldn’t have been more convenient. "
The price is €554
includes taxes & fees
9 Mar - 10 Mar
The Cozy Little Cottage!

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (133)
"We enjoyed our stay, would stay again. Communication was excellent. Property is just as pictured. Great location, great value for the price. Could use a little freshening up, light bulb in laundry room, etc."
The price is €471
includes taxes & fees
2 Mar - 3 Mar
Cottage with Pool and Dockage, just minutes to Key West

DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

9.2 out of 10, Wonderful, (188)
"This was a great property. Nice and quiet. Gated for privacy. Would use again and will recommend. "
DUVAL SQUARE, KEY WEST Lovely 2 Bedroom 2.5 Bath Condo in a GREAT Location!

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

9.4 out of 10, Exceptional, (217)
"We have traveled to KW every winter for several years. This place is by far the best combination of location and space. Will be back. "
The price is €618
includes taxes & fees
10 Mar - 11 Mar
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Captain's Daughter: Oversized home for the whole family w/private pool & dock

9.8 out of 10, Exceptional, (122)
"Our stay was absolutely incredible. The condo was bigger than we were expecting so we had plenty of room to spread out and relax. The property management website was super helpful and the customer service was amazing as well! Nothing but good reviews from everyone who stayed there!"
Captain's Daughter: Oversized home for the whole family w/private pool & dock
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

Beachside Resort & Residences

3.5 star property
8.4 out of 10, Very good, (1014)
"We had a great stay"
The price is €326
includes taxes & fees
1 Apr - 2 Apr
Beachside Resort & Residences

Southernmost Beach Resort

4.0 star property
8.6 out of 10, Excellent, (2301)
"Beautiful location - the beach was 50 feet from our door … and great cafes and bars both on the property and within easy walking distance. The concierge was very helpful in arranging reservations for snorkeling and sunset cruises. We enjoyed the free breakfast every morning. Our only complaint is that time went by so fast!"
The price is €560
includes taxes & fees
12 Mar - 13 Mar
Southernmost Beach Resort

Oceans Edge Key West Resort, Hotel & Marina

4.0 star property
8.8 out of 10, Excellent, (1592)
"We loved it all! From the marina views, tiki hut activities, restaurant was excellent! And the staff. Would absolutely go again!"
The price is €439
includes taxes & fees
31 Mar - 1 Apr
Oceans Edge Key West Resort, Hotel & Marina
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?

Feb 3-10 $245 off the rates close beach full kitchen & patio: This holiday home rental outside of Cow Key is located in the city centre, and offers a patio, air conditioning and WiFi to help you feel perfectly comfortable 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 wider area, you’ll find Duval Street and Stock Island Yacht Club & Marina.

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.