Cow Key Vacation Rentals

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Check prices for these dates

Tonight
Jun 24 - Jun 25
Tomorrow
Jun 25 - Jun 26
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Cow Key

Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (150)
"Nice,clean, pet friendly, helpful "
Aqua Lodges at Hurricane Hole Marina
VanGogh Studio | Updated, Old Town, Heated Pool
1 bedroom, free WiFi, bed sheets

VanGogh Studio | Updated, Old Town, Heated Pool

8.4 out of 10, Very Good, (22)
"We loved our stay. The room was great, small but all we needed. "
The price is ￥12,869
￥39,057 total
includes taxes & fees
Jul 1 - Jul 2
VanGogh Studio | Updated, Old Town, Heated Pool
Heart of Downtown Key West Cottage With Off-Street Parking
Exterior

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (129)
"Perfect spot for small group or couple to stay one block over from Duval St. Highly recommend staying here!"
Heart of Downtown Key West Cottage With Off-Street Parking
Coconut Mallory Resort And Marina By Kees Vacations
2 outdoor pools

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (814)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Miscellaneous

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

8.0 out of 10, Very Good, (9)
"Kevin and Capt. Phil were great hosts. Would definitely stay there again. "
The price is ￥18,385
￥76,403 total
includes taxes & fees
Jun 27 - Jun 28
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Flat-screen TV, DVD player, stereo

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (177)
"We would definitely stay here again! Great location, exactly as described, overall great place."
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Beach nearby

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

9.6 out of 10, Exceptional, (137)
"We loved everything about it, the place was spotless and although the Havana room is quite small, we didn't spend much time there. Walkable to Duval Street and just a very pleasant property."
The price is ￥12,548
￥34,016 total
includes taxes & fees
Jun 25 - Jun 26
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
Interior

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.0 out of 10, Wonderful, (10)
"Great time staying there "
The price is ￥14,153
￥36,114 total
includes taxes & fees
Jul 2 - Jul 3
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Beach nearby

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (135)
"The property was exactly as listed. Great location, well kept, clean, and easy to check into. I don’t even know how I’d improve upon the experience, it was great. Parking on site was great as well! "
The price is ￥15,175
￥37,409 total
includes taxes & fees
Jul 2 - Jul 3
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
A heated pool

Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

8.8 out of 10, Excellent, (18)
"Property as described in listing, enjoyed our stay! Would def stay again! "
The price is ￥14,182
￥40,519 total
includes taxes & fees
Jul 1 - Jul 2
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (389)
"Beautiful place and weather "
The price is ￥13,519
￥33,484 total
includes taxes & fees
Jun 25 - Jun 26
Steps from Duval, Pool on Site & Bikes Included!
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Beach nearby

CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!

9.8 out of 10, Exceptional, (114)
"Excellent location, walkable to Duval Street. We were able to park on-site and walk to everything. We would definitely stay here again."
The price is ￥12,986
￥34,509 total
includes taxes & fees
Jun 25 - Jun 26
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
THE FLAGLER ROOM @ Inn on Fleming ~ ADULTS ONLY 1st Floor King & Shared Pool
Interior

THE FLAGLER ROOM @ Inn on Fleming ~ ADULTS ONLY 1st Floor King & Shared Pool

8.8 out of 10, Excellent, (16)
"Great location and a lovely restored home. The common area was fabulous, with a full kitchen, eating/gathering area, and a small plunge pool. Room was nice but needed a few repairs. Bathroom vanity was worn and needs replacing. The appearance of some small bugs was disturbing but quickly addressed. Overall a nice place to stay. "
The price is ￥14,007
￥35,949 total
includes taxes & fees
Jun 29 - Jun 30
THE FLAGLER ROOM @ Inn on Fleming ~ ADULTS ONLY 1st Floor King & Shared Pool
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
A heated pool

IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!

9.4 out of 10, Exceptional, (173)
"Really enjoyed the place, very clean and comfortable, great balcony overlooking the ocean. The amenities like the pool and hot tub were very nice and it's a short bike / drive / Lyft from everything in Key West. "
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
A heated pool

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

9.8 out of 10, Exceptional, (101)
"Excellent property and location! Really enjoyed the property!"
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
Coming Soon July 1! The Jolly Rooster New! 2BR/2BA - Walk to Duval
Exterior

Coming Soon July 1! The Jolly Rooster New! 2BR/2BA - Walk to Duval

The price is ￥45,962
￥85,960 total
includes taxes & fees
Jul 5 - Jul 6
Coming Soon July 1! The Jolly Rooster New! 2BR/2BA - Walk to Duval
CLASSIC HATTERAS MOTOR YACHT LOCATED AT THE PERRY MARINA, A 5-STAR RESORT.
Property grounds

CLASSIC HATTERAS MOTOR YACHT LOCATED AT THE PERRY MARINA, A 5-STAR RESORT.

The price is ￥25,680
￥66,846 total
includes taxes & fees
Jul 10 - Jul 11
CLASSIC HATTERAS MOTOR YACHT LOCATED AT THE PERRY MARINA, A 5-STAR RESORT.
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
1 bedroom, WiFi, bed sheets

Yellowfin Ledge | Inviting Getaway On Duval! Balcony!

9.4 out of 10, Exceptional, (17)
"This property was in a perfect location in Key West. Just outside the downtown craziness. Everything right in walking distance. "
The price is ￥12,869
￥40,990 total
includes taxes & fees
Jul 1 - Jul 2
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
Pool

ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

9.8 out of 10, Exceptional, (205)
"The place is beautiful and every convenience thought of. Would definitely stay here Asian! "
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
Duval Delight | Recently Remodeled Condo on Duval!
Terrace/patio

Duval Delight | Recently Remodeled Condo on Duval!

9.8 out of 10, Exceptional, (21)
"The unit is awesome - perfect location on Duval St, very comfortable beds, plenty of space. Will definitely be back!"
The price is ￥30,203
￥77,034 total
includes taxes & fees
Jul 1 - Jul 2
Duval Delight | Recently Remodeled Condo on Duval!
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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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?

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!: Visitors like this Cow Key vacation home rental. It is located in the city center and offers a patio, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.