Cow Key Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in Cow Key

Our top choices for Cow Key vacation rentals

Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"The stay was beautiful "
The price is ￥12,504
￥38,832 total
includes taxes & fees
Aug 28 - Aug 29
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Exterior

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (312)
"EXCELENT LOCATION AND SUNSET VIEW"
The price is ￥38,628
￥47,612 total
includes taxes & fees
Sep 2 - Sep 3
Hyatt Vacation Club at Sunset Harbor, Key West
Steps from Duval, Pool on Site & Bikes Included!
Exterior

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (397)
"this was exactly as advertised and close to all the action"
The price is ￥13,138
￥33,545 total
includes taxes & fees
Sep 4 - Sep 5
Steps from Duval, Pool on Site & Bikes Included!
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, (140)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is ￥14,008
￥36,311 total
includes taxes & fees
Sep 4 - Sep 5
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
Beach nearby

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

9.4 out of 10, Exceptional, (11)
"Great time staying there "
The price is ￥12,976
￥35,002 total
includes taxes & fees
Sep 7 - Sep 8
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
Beach nearby

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

9.8 out of 10, Exceptional, (18)
"Great place will rent again "
The price is ￥12,976
￥35,002 total
includes taxes & fees
Sep 8 - Sep 9
THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Exterior

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (181)
"Place is centrally located which is ideal for walking from place to place. House was very clean and had everything needed for my time spent there"
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
1 bedroom, free WiFi, bed sheets

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is ￥11,943
￥46,131 total
includes taxes & fees
Sep 9 - Sep 10
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Claude Monet Suite | Cozy Studio with Pool & Patio Access!
Terrace/patio

Claude Monet Suite | Cozy Studio with Pool & Patio Access!

9.4 out of 10, Exceptional, (20)
"Great location. Everything was perfect!"
The price is ￥12,262
￥38,456 total
includes taxes & fees
Sep 16 - Sep 17
Claude Monet Suite | Cozy Studio with Pool & Patio Access!
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!
Beach nearby

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

9.2 out of 10, Wonderful, (16)
"I was initially worried because I normally would only book with a property that had quite a bit of reviews. I'm glad I trusted my instincts to go with the Inn on Fleming! The room looked exactly as pictured. The whole lodge had a cute charm to it. Perfect place to stay when visiting the keys."
The price is ￥18,284
￥43,665 total
includes taxes & fees
Sep 4 - Sep 5
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared 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, (134)
"May not be a better location"
Heart of Downtown Key West Cottage With Off-Street Parking
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
Exterior detail

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (15)
"Great place to stay! Very clean and steps to Duval Ave."
The price is ￥14,450
￥55,652 total
includes taxes & fees
Sep 10 - Sep 11
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (296)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Property grounds

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

8.8 out of 10, Excellent, (55)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: great place, great location! we'll be back year after year!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
Beach

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

9.6 out of 10, Exceptional, (188)
"The location was perfect for exploring and getting places in key West. It had a relaxing vibe that was perfect for vacation. "
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
Beach nearby

ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!

9.6 out of 10, Exceptional, (131)
"This was a clean property which had everything including an ice machine and filttered water machine! Friendly professional people who work there and have thought of every extra touch to make your stay worry free! Great pool,and I stayed at the top "treehouse" room which had 2 sets of stairs to get to it. It was a large room and I enjoyed it with my own private deck!"
The price is ￥14,450
￥36,808 total
includes taxes & fees
Sep 9 - Sep 10
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Terrace/patio

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

9.6 out of 10, Exceptional, (8)
"The units were perfect and the customer service was amazing. "
The price is ￥37,895
￥123,649 total
includes taxes & fees
Sep 7 - Sep 8
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
A heated pool

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

9.8 out of 10, Exceptional, (44)
"Wonderful view, lot's of space, great location "
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
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, (142)
"We had a great stay places is amazing"
The price is ￥13,418
￥35,500 total
includes taxes & fees
Sep 9 - Sep 10
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Sport court

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

9.0 out of 10, Wonderful, (26)
"Great place, great location, great communication from host!"
The price is ￥33,978
￥57,191 total
includes taxes & fees
Aug 28 - Aug 29
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
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

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Out of the world experience. The bathroom and kitchen were luxurious and we loved our stay."
Balaji 1-night trip
Posted 20 hours ago
Hyatt Vacation Club at Beach House, Key West

Find out more about Cow Key

Find out more about Cow Key

Search for holiday rentals in Cow Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Cow Key using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Cow Key while they last

Look no further and take a look at our great range of rental properties in Cow Key!

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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?

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!: Visitors like this Cow Key vacation home rental. It is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 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.