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, (161)
"The stay was beautiful "
The price is €203
includes taxes & fees
31 Aug - 1 Sept
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 €273
includes taxes & fees
27 Aug - 28 Aug
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 €199
includes taxes & fees
4 Sept - 5 Sept
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 €216
includes taxes & fees
26 Aug - 27 Aug
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 €199
includes taxes & fees
27 Aug - 28 Aug
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 €223
includes taxes & fees
26 Aug - 27 Aug
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 €270
includes taxes & fees
26 Aug - 27 Aug
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 €259
includes taxes & fees
2 Sept - 3 Sept
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 €331
includes taxes & fees
1 Sept - 2 Sept
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 €219
includes taxes & fees
26 Aug - 27 Aug
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 €719
includes taxes & fees
31 Aug - 1 Sept
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

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!

9.6 out of 10, Exceptional, (142)
"We had a great stay places is amazing"
The price is €211
includes taxes & fees
27 Aug - 28 Aug
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 €339
includes taxes & fees
26 Aug - 27 Aug
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 €270
includes taxes & fees
27 Aug - 28 Aug
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 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?

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!: This holiday home rental outside of Cow Key is located in the city centre, and offers a BBQ, 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 that 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 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.