Cow Key Vacation Rentals

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Our top choices for Cow Key vacation rentals

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (185 reviews)
"Clean, great view, wonderful porch, comfortable bed"
United States
Karen H.
The price is CA $302
CA $615 total
includes taxes & fees
May 14 - May 15
Waterfront Home

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is CA $469
CA $655 total
includes taxes & fees
May 27 - May 28
Resort View 1BR Suite With Direct Pool Access

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

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (88 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is CA $341
CA $771 total
includes taxes & fees
May 28 - May 29
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (14 reviews)
"Host was great!!! Unit very clean well stocked with beautiful view."
United States
Lisa F.
The price is CA $308
CA $652 total
includes taxes & fees
Jun 2 - Jun 3
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is CA $273
CA $824 total
includes taxes & fees
May 18 - May 19
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
9.0 out of 10, Wonderful, (61 reviews)
"The location was very good and the host was responsive. "
United States
Lilly A.
The price is CA $277
CA $551 total
includes taxes & fees
May 21 - May 22
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D
Old Town Key West
9.8 out of 10, Exceptional, (37 reviews)
"What a great place to spend a long weekend! The rooms were very clean, and communication and entry/exit from the property were super easy. Will definitely recommend this location for a vacation stay."
United States
Whitney G.
The price is CA $119
CA $514 total
includes taxes & fees
May 28 - May 29
Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

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, (47 reviews)
"Clean room. I wasn’t aware it was a micro hotel but that’s ok."
United States
Michael
The price is CA $119
CA $434 total
includes taxes & fees
May 17 - May 18
Salvador's Seclusion | Cozy Studio Retreat w/ Heated 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 CA $683
CA $1,322 total
includes taxes & fees
May 14 - May 15
Oceanfront 2BR Retreat | 35' Dock, Open Views, Boater's Paradise

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (99 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveller
The price is CA $277
CA $580 total
includes taxes & fees
May 18 - May 19
Canal front, dockage, 2 bedroom, 2 bath

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!
Old Town Key West
9.8 out of 10, Exceptional, (33 reviews)
"The property was cozy and a great location for walking."
United States
Elizabeth E.
The price is CA $119
CA $451 total
includes taxes & fees
May 17 - May 18
Scott's Cottage - Truman @ Duval | Perfect Spot in Old Town Key West!

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (168 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is CA $479
CA $956 total
includes taxes & fees
Jun 3 - Jun 4
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

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 CA $769
CA $1,404 total
includes taxes & fees
May 28 - May 29
Atlantic View Luxury Villa with Pool

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (25 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is CA $479
CA $926 total
includes taxes & fees
May 18 - May 19
Spanish Queen @Venture Out, Cudjoe Key

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, (30 reviews)
"The view to watch the sunrise was amazing for our stay. House was clean and easy instructions to get inside. "
United States
Megan M.
The price is CA $430
CA $891 total
includes taxes & fees
Jun 7 - Jun 8
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

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 CA $503
CA $1,212 total
includes taxes & fees
May 14 - May 15
Post Card Point #319 - Ocean Views!

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (14 reviews)
"We rented a boat, fished and snorkeled. Really enjoyed the patio right on the sea wall. One of the best parts of property was the stunning view of the morning sunrise!"
United States
Matt W.
The price is CA $479
CA $1,192 total
includes taxes & fees
May 20 - May 21
House of the Rising Sun - VO479

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"It was great. House was amazing"
United States
Ernest H.
The price is CA $819
CA $1,992 total
includes taxes & fees
May 20 - May 21
Springtide House at Lunara Bay

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 CA $476
CA $899 total
includes taxes & fees
May 21 - May 22
Grand Marina Suite by Brightwild Waterfront

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (146 reviews)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
The price is CA $683
CA $1,352 total
includes taxes & fees
May 26 - May 27
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & 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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cow Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Sugarloaf Key RV Resort & Cottages: Visitors like this Cow Key vacation home rental. It is located near a metro station and offers an outdoor pool, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

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 Florida Keys Beaches. In the larger area, you’ll find Duval Street and Key West Tropical Forest and Botanical Garden.

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.