Cow Key Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
29 Jun - 30 Jun
Tomorrow
30 Jun - 1 Jul
Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul

Holiday Rentals in Cow Key

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, (304)
"We had a nice stay. The property was in a great location."
The price is HK$1,943
HK$2,406 total
includes taxes & fees
22 Jul - 23 Jul
Hyatt Vacation Club at Sunset Harbor, Key West
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (151)
"I love the area and the restaurant, it’s quite and relaxing "
The price is HK$541
HK$1,925 total
includes taxes & fees
16 Jul - 17 Jul
Aqua Lodges at Hurricane Hole Marina
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
Meeting facility

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
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, (136)
"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 HK$777
HK$1,968 total
includes taxes & fees
2 Jul - 3 Jul
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Marina

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 HK$933
HK$4,318 total
includes taxes & fees
7 Jul - 8 Jul
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Interior

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

10.0 out of 10, Exceptional, (7)
"The ideal getaway, I brought a grill and a pan and did all the cooking outside on the deck. Took paddle boards through mangrove tunnels and saw tons of fish. Had a baby sea turtle swim up to the boat. "
The price is HK$1,272
HK$2,116 total
includes taxes & fees
3 Jul - 4 Jul
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
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, (177)
"We would definitely stay here again! Great location, exactly as described, overall great place."
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Steps from Duval, Pool on Site & Bikes Included!
Exterior

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (390)
"Beautiful place and weather "
The price is HK$727
HK$1,817 total
includes taxes & fees
3 Jul - 4 Jul
Steps from Duval, Pool on Site & Bikes Included!
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

9.0 out of 10, Wonderful, (10)
"Great time staying there "
The price is HK$754
HK$1,934 total
includes taxes & fees
2 Jul - 3 Jul
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
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 HK$746
HK$1,933 total
includes taxes & fees
9 Jul - 10 Jul
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
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, (206)
"great property"
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
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 HK$691
HK$2,084 total
includes taxes & fees
15 Jul - 16 Jul
VanGogh Studio | Updated, Old Town, Heated Pool
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 HK$1,608
HK$3,858 total
includes taxes & fees
8 Jul - 9 Jul
CLASSIC HATTERAS MOTOR YACHT LOCATED AT THE PERRY MARINA, A 5-STAR RESORT.
THE FLAGLER ROOM @ Inn on Fleming ~ ADULTS ONLY 1st Floor King & Shared Pool
Beach nearby

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 HK$722
HK$1,907 total
includes taxes & fees
1 Jul - 2 Jul
THE FLAGLER ROOM @ Inn on Fleming ~ ADULTS ONLY 1st Floor King & Shared Pool
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Terrace/patio

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

10.0 out of 10, Exceptional, (16)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is HK$691
HK$2,515 total
includes taxes & fees
2 Jul - 3 Jul
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
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, (49)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
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 HK$691
HK$2,091 total
includes taxes & fees
1 Jul - 2 Jul
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Beach nearby

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

9.8 out of 10, Exceptional, (87)
"Couldnt have picked a mire perfect place for my Wife and I's short trip. Location was excellent close to everything. Place was beyond clean and very quiet in the evenings. We will stay here again!"
The price is HK$958
HK$2,499 total
includes taxes & fees
6 Jul - 7 Jul
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
The Salt Cay | Updated! Stunning Sunset View, Pool!
A heated pool

The Salt Cay | Updated! Stunning Sunset View, Pool!

10.0 out of 10, Exceptional, (17)
"We had a wonderful stay and would definitely recommend this property! "
The price is HK$1,177
HK$3,167 total
includes taxes & fees
22 Jul - 23 Jul
The Salt Cay | Updated! Stunning Sunset View, Pool!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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?

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!: This holiday home rental outside of Cow Key is located in the city centre, 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 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.