Cow Key Holiday Rentals

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Our top choices for Cow Key holiday rentals

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (167 reviews)
"Great place "
United States
David
The price is HK$1,586
HK$3,003 total
includes taxes & fees
22 Apr - 23 Apr
Cottage with Pool and Dockage, just minutes to Key West

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is HK$1,559
HK$3,911 total
includes taxes & fees
22 Apr - 23 Apr
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (180 reviews)
"Place was as advertised! We LOVE Venture out! There are park rules but if you follow them, you become family! Home was stocked and clean. Screened in back patio was a nice touch! Would stay in this unit again!"
United States
Thomas B.
The price is HK$1,763
HK$3,533 total
includes taxes & fees
11 Apr - 12 Apr
Waterfront Home

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is HK$4,406
HK$8,040 total
includes taxes & fees
21 Apr - 22 Apr
Atlantic View Luxury Villa with Pool

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (106 reviews)
"Janet and Jerry were excellent hosts and the property was perfect for our trip "
United States
Shayne H.
The price is HK$1,559
HK$3,911 total
includes taxes & fees
13 Apr - 14 Apr
SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (22 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is HK$2,742
HK$5,362 total
includes taxes & fees
21 Apr - 22 Apr
Spanish Queen @Venture Out, Cudjoe Key

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (182 reviews)
"Great stay better than we expected "
Canada
Jordan
The price is HK$1,239
HK$2,707 total
includes taxes & fees
22 Apr - 23 Apr
Aqua Lodges at Hurricane Hole Marina

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.6 out of 10, Good, (34 reviews)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is HK$1,959
HK$3,956 total
includes taxes & fees
22 Apr - 23 Apr
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (96 reviews)
"We had a great time and will be back. "
United States
Michelle K.
The price is HK$2,820
HK$6,058 total
includes taxes & fees
21 Apr - 22 Apr
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful "
United States
Lisa P.
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina
Stock Island
The price is HK$776
HK$5,363 total
includes taxes & fees
13 Apr - 14 Apr
Yacht in Key West - Hosted by Luxury Sea Charters @ The Perry Marina

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (36 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is HK$2,342
HK$4,798 total
includes taxes & fees
14 Apr - 15 Apr
Paradise found

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (28 reviews)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is HK$3,054
HK$5,286 total
includes taxes & fees
12 Apr - 13 Apr
Grand Marina Suite by Brightwild Waterfront

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (54 reviews)
"Great location in the complex and in the Keys themselves."
United States
Karl S.
The price is HK$3,085
HK$7,132 total
includes taxes & fees
20 Apr - 21 Apr
Post Card Point #319 - Ocean Views!

The Salt Cay | Updated! Stunning Sunset View, Pool

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (46 reviews)
"Great place with great location , good for families "
United States
Dennys P.
The price is HK$2,223
HK$4,990 total
includes taxes & fees
10 May - 11 May
The Salt Cay | Updated! Stunning Sunset View, Pool

Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise

Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise
Cudjoe Key
9.6 out of 10, Exceptional, (53 reviews)
"Great place!"
United States
Piotr P.
The price is HK$3,907
HK$7,507 total
includes taxes & fees
24 Apr - 25 Apr
Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (43 reviews)
"Every as described, great stay!"
United States
Bryan W.
The price is HK$1,792
HK$4,378 total
includes taxes & fees
15 Apr - 16 Apr
The Cat Island Suite | Charmingly Renovated w/ Pool

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is HK$6,259
HK$13,393 total
includes taxes & fees
14 Apr - 15 Apr
Capmar House at Lunara Bay

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Old Town Key West
8.6 out of 10, Excellent, (42 reviews)
"Loved the laundry access and the fact that the host left laundry Tide in the room! Amazing pool, perfect walking location to every thing. "
United States
Sara S.
The price is HK$1,017
HK$2,716 total
includes taxes & fees
12 Apr - 13 Apr
Salvador's Seclusion | Cozy Studio Retreat w/ Heated 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.
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Top Cow Key Hotel Reviews

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

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?

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!: This holiday home rental outside of Cow Key is located on the waterfront, and has a balcony, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.