Cow Key Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 28 - Oct 29
Tomorrow
Oct 29 - Oct 30
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in Cow Key

Restaurant
Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (165)
"The stay was beautiful "
United States
Jennifer
The price is ￥13,337
￥40,606 total
includes taxes & fees
Oct 29 - Oct 30
Aqua Lodges at Hurricane Hole Marina
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very Good, (314)
"Great hotel with excellent location "
United States
Rony
The price is ￥33,468
￥42,809 total
includes taxes & fees
Oct 29 - Oct 30
Hyatt Vacation Club at Sunset Harbor, Key West
Exterior
Steps from Duval, Pool on Site & Bikes Included!
Steps from Duval, Pool on Site & Bikes Included!
9.6 out of 10, Exceptional, (406)
"this was exactly as advertised and close to all the action"
Canada
Dave T.
The price is ￥13,609
￥34,595 total
includes taxes & fees
Nov 5 - Nov 6
Steps from Duval, Pool on Site & Bikes Included!
Meeting facility
Coconut Mallory Resort And Marina By Kees Vacations
Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
8.2 out of 10, Very Good, (820)
"Great place really nice rooms"
United States
Eric
Coconut Mallory Resort And Marina By Kees Vacations
Terrace/patio
Duval Delight | Recently Remodeled Condo on Duval!
Duval Delight | Recently Remodeled Condo on Duval!
9.8 out of 10, Exceptional, (34)
"This place has everything you need and is in an excellent location. We would definitely stay here again. "
United States
Kimberly D.
The price is ￥19,566
￥63,770 total
includes taxes & fees
Oct 30 - Oct 31
Duval Delight | Recently Remodeled Condo on Duval!
Outdoor pool, a heated pool
Perfect Location, Private Heated Pool, Pristine Luxury Home!
Perfect Location, Private Heated Pool, Pristine Luxury Home!
10.0 out of 10, Exceptional, (191)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
The price is ￥145,103
￥286,980 total
includes taxes & fees
Nov 4 - Nov 5
Perfect Location, Private Heated Pool, Pristine Luxury Home!
Apartment | 1 bedroom
Island View 1BR Residence With Balcony
Island View 1BR Residence With Balcony
2.0 star property
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
The price is ￥39,578
￥57,515 total
includes taxes & fees
Oct 29 - Oct 30
Island View 1BR Residence With Balcony
Exterior
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
9.2 out of 10, Wonderful, (183)
"Great location; excellent property management "
United States
Frank T.
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Beach
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
8.6 out of 10, Excellent, (138)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is ￥20,925
￥54,549 total
includes taxes & fees
Nov 2 - Nov 3
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Marina
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
6.6 out of 10, (12)
"Unfortunately this stay was very disappointing. The marina was awesome. Tessa was awesome. The boat itself was disgusting. The pictures are very deceiving. What you see is not what you get. "
United States
Christine
The price is ￥27,134
￥55,078 total
includes taxes & fees
Nov 3 - Nov 4
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Marina
Living the Dream Key West Style
Living the Dream Key West Style
9.8 out of 10, Exceptional, (30)
"We thoroughly enjoyed our stay on Serenity! The location was perfect, the hosts were friendly and accommodating, and the boat is spacious and comfortable. I hope to be back aboard Serenity soon! "
United States
Alison
The price is ￥41,102
￥52,046 total
includes taxes & fees
Nov 11 - Nov 12
Living the Dream Key West Style
A heated pool
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
9.8 out of 10, Exceptional, (48)
"Wonderful view, lot's of space, great location "
United States
Valerie
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
Exterior
Heart of Downtown Key West Cottage With Off-Street Parking
Heart of Downtown Key West Cottage With Off-Street Parking
10.0 out of 10, Exceptional, (139)
"Perfect location! Cute cottage had the best time. "
United States
jamie r.
Heart of Downtown Key West Cottage With Off-Street Parking
Beach nearby
WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool
WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool
9.6 out of 10, Exceptional, (14)
"Great time staying there "
United States
Loretta C.
The price is ￥17,107
￥39,923 total
includes taxes & fees
Nov 1 - Nov 2
WHITEHEAD ROOM @ Inn on Fleming~ADULTS ONLY 2nd Lvl Queen Shared Heated Pool
Fridge, stovetop, coffee/tea maker, toaster
Super-Cozy boat in Key West!
Super-Cozy boat in Key West!
The price is ￥38,032
￥48,285 total
includes taxes & fees
Nov 10 - Nov 11
Super-Cozy boat in Key West!
On the beach, beach towels
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (238)
"Lovely property. Well equipped, nicely decorated, perfect for our stay."
United States
Karen M.
The price is ￥53,459
￥124,885 total
includes taxes & fees
Oct 29 - Oct 30
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
Terrace/patio
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
10.0 out of 10, Exceptional, (23)
"Will stay here again "
United States
Matt O.
The price is ￥24,438
￥64,399 total
includes taxes & fees
Nov 13 - Nov 14
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
1 bedroom, free WiFi, bed sheets
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
10.0 out of 10, Exceptional, (23)
"We had a wonderful stay here with our kids. Can’t beat the location."
United States
Julia P.
The price is ￥15,579
￥49,729 total
includes taxes & fees
Oct 29 - Oct 30
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Terrace/patio
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
9.2 out of 10, Wonderful, (97)
"Great space for a large party! Having both houses with the driveway in the middle provided a great spot for our weekend!"
United States
Ryan F.
The price is ￥55,139
￥138,686 total
includes taxes & fees
Nov 13 - Nov 14
Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
Terrace/patio
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
9.8 out of 10, Exceptional, (24)
"Everything was really good"
United States
Rose M.
The price is ￥15,732
￥52,208 total
includes taxes & fees
Oct 30 - Oct 31
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cow Key Hotel Reviews

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

10/10 Excellent
"This was my 4th year in a row staying at this property. Great views and a great location. "
JEFFREY 3-night trip
Posted 13 hours ago
Oceans Edge Key West Resort, Hotel & Marina

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:

  • View our selection of featured holiday rentals in Cow Key
  • Use the map to find apartments and other holiday homes in the Cow Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cow Key while they last

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

Explore a world of travel with Expedia

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?

Perfect Location, Private Heated Pool, Pristine Luxury Home!: Visitors like this Cow Key vacation home rental. It is located in the city center and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.