Cow Key Vacation Rentals

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Vacation Rentals in Cow Key

Our top choices for Cow Key vacation rentals

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (161)
"The stay was beautiful "
The price is CA $82
CA $325 total
includes taxes & fees
Aug 24 - Aug 25
Aqua Lodges at Hurricane Hole Marina

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 CA $351
CA $434 total
includes taxes & fees
Aug 27 - Aug 28
Hyatt Vacation Club at Sunset Harbor, Key West

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 CA $123
CA $315 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!

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 CA $131
CA $340 total
includes taxes & fees
Aug 25 - Aug 26
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

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 CA $111
CA $310 total
includes taxes & fees
Aug 24 - Aug 25
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (179)
"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!

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

9.4 out of 10, Exceptional, (20)
"Great location. Everything was perfect!"
The price is CA $109
CA $352 total
includes taxes & fees
Aug 24 - Aug 25
Claude Monet Suite | Cozy Studio with Pool & Patio Access!

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 CA $108
CA $429 total
includes taxes & fees
Aug 26 - Aug 27
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

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

9.2 out of 10, Wonderful, (16)
"We had a great time at this property. The owner is super attentive to detail and immediately responds to any questions or requests. You can really tell that they CARE about their property and guests. Property is well cared for and charming. Highly recommend!"
The price is CA $163
CA $399 total
includes taxes & fees
Aug 24 - Aug 25
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

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!

9.6 out of 10, Exceptional, (15)
"Great place to stay! Very clean and steps to Duval Ave."
The price is CA $151
CA $543 total
includes taxes & fees
Sep 1 - Sep 2
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

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

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!

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 CA $135
CA $341 total
includes taxes & fees
Aug 24 - Aug 25
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!

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 CA $337
CA $1,135 total
includes taxes & fees
Aug 31 - Sep 1
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

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

10.0 out of 10, Exceptional, (42)
"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!

9.6 out of 10, Exceptional, (142)
"We had a great stay places is amazing"
The price is CA $126
CA $333 total
includes taxes & fees
Aug 27 - Aug 28
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

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 CA $318
CA $534 total
includes taxes & fees
Aug 24 - Aug 25
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (19)
"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 location and very nice room"
The price is CA $108
CA $429 total
includes taxes & fees
Aug 27 - Aug 28
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (3)
"Beautiful property, perfectly located, and one of the best VRBO experiences we have ever had."
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
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

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.