A sunset over a beach with a wooden pier and a small structure on it.

Cow Key Vacation Rentals

Q: 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.

Dates

November 2026

December 2026

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Our top choices for Cow Key vacation rentals

A row of floating houses with balconies, connected by walkways, on calm water.

1. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

￥46,528 total

includes taxes & fees

Nov 10 - Nov 11

A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

2. The Grand Cayman | Beautifully Remodeled Key West!

Key West

Matt R.

￥74,563 total

includes taxes & fees

Nov 21 - Nov 22

A wooden deck with a large tree, outdoor seating, and a marina in the background.

3. Poolside Cottage #412

Key West

shannon b.

￥47,940 total

includes taxes & fees

Nov 29 - Nov 30

A pathway leading to a covered outdoor seating area with a table and chairs, surrounded by lush greenery and trees.

4. Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

Old Town Key West

Victoria T.

A living room with a grey sofa, wooden chairs, a glass coffee table, and a kitchen in the background.

5. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

Key West

Teri K.

￥77,247 total

includes taxes & fees

Nov 16 - Nov 17

A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

6. Poolside Cottage #411

Key West

Jennifer W.

￥49,216 total

includes taxes & fees

Dec 1 - Dec 2

A white building with a covered porch and a palm tree.

7. Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West

Laura D.

￥41,242 total

includes taxes & fees

Nov 18 - Nov 19

A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

8. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

Old Town Key West

Amanda G.

￥56,383 total

includes taxes & fees

Dec 2 - Dec 3

A wooden bridge leading to a house with a sign indicating no swimming or diving.

9. The Tortuga at Sunrise Suites - Balcony & Pool

Key West

Margaret G.

￥79,459 total

includes taxes & fees

Dec 1 - Dec 2

A balcony with a table and chairs, overlooking a marina with boats and a clear sky.

10. Waterfront Dock Pool Key West Near Duval

Meadows

Chrystalbelle R.

￥66,223 total

includes taxes & fees

Nov 8 - Nov 9

A pool area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

11. Leo's Lodge | Newly Updated!

Old Town Key West

Blake

￥51,324 total

includes taxes & fees

Nov 29 - Nov 30

A tropical garden pathway leading to a building with a yellow facade and green shutters.

12. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Old Town Key West

Justin D.

￥67,801 total

includes taxes & fees

Dec 2 - Dec 3

A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

13. The Cat Island Suite | Charmingly Renovated w/ Pool

Key West

Patti E.

￥74,787 total

includes taxes & fees

Nov 9 - Nov 10

14. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Old Town Key West

walter l.

A covered porch with white wooden railings, wicker furniture, and hanging lanterns.

15. Duval Delight | Recently Remodeled Condo on Duval!

Old Town Key West

Jennifer

￥76,879 total

includes taxes & fees

Nov 11 - Nov 12

A small, private entrance to a house with a brick pathway leading to a door.

16. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Old Town Key West

Brian R.

￥57,416 total

includes taxes & fees

Nov 17 - Nov 18

A narrow brick pathway flanked by white buildings with potted plants and a bench.

17. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

Old Town Key West

Jay M.

￥57,761 total

includes taxes & fees

Nov 16 - Nov 17

A multi-level wooden house with a blue staircase and white railings.

18. Underwater Cabana at Custom House Inn | On Duval!

Key West Historic District

"We had a great comunication with the host. They were very responsive to all my questions and concerns. The check in process was very easy. They helped me with my car and shuttled me to the unit. The place was right on Duval Street. Although like that not very noisy as it was at the back. You could be in your room and at the bar for music and drinks in a minute. The room was comfortable and clean. If I go back to Key West again, I will not look for any other place to stay than Custom House."

EMIN

￥69,545 total

includes taxes & fees

Nov 10 - Nov 11

A modern living room with a sofa, coffee table, and a painting of a beach scene.

19. The Saint Kitts Suite | Breathtaking View, Heated Pool

Key West

Rolando

￥74,098 total

includes taxes & fees

Nov 29 - Nov 30

A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

20. Chagall's Corner | Newly Remodeled!

Old Town Key West

Maria B.

￥51,003 total

includes taxes & fees

Nov 15 - Nov 16

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Find vacation rentals that suit your style

Top Cow Key Hotel Reviews

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

Hampton Inn Key West FL

Key West

10/10 Excellent

Karen

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

Hyatt Vacation Club at Windward Pointe, Key West

Key West

10/10 Excellent

Lindsay

A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

Hyatt Vacation Club at Beach House, Key West

Key West

10/10 Excellent

Sonia

A resort pool with clear blue water, surrounded by palm trees and lounge chairs.

Havana Cabana at Key West

New Town

10/10 Excellent

Eliana

A pool area with lounge chairs and gazebos, surrounded by palm trees.

DoubleTree Resort by Hilton Grand Key - Key West

Key West

10/10 Excellent

Hector

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

10/10 Excellent

william

A wooden archway leading to a pool area surrounded by lush tropical vegetation.

Parrot Key Hotel & Villas

Northside Resort

10/10 Excellent

Great for a relaxing weekend, quiet hotel not too far from the main tourist center. We love the shuttle service provided by the hotel and his driver Gerry who guided us in every short trips. The only advice to the hotel is to provide the housekeeping service everyday without being requested by the guest, we expected this service to be included since the hotel charged an extra 51.00 usd per night!

CARLOS

A swimming pool with water splashing, surrounded by palm trees and a building in the background.

Silver Palms Inn & Historic Homes

Old Town Key West

10/10 Excellent

Janice

A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

Opal Key Resort & Marina, Key West

Old Town Key West

10/10 Excellent

Jose

A hotel with a swimming pool, balconies, and a view of the sea.

Hyatt Centric Key West Resort and Spa

Key West Historic District

10/10 Excellent

Lisa

A pool area with lounge chairs and a table, surrounded by palm trees.

Orchid Key Inn - Adults Only

Old Town Key West

10/10 Excellent

Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...

Courtney

A two-story house with a covered porch, a brick pathway, and a large tree.

The Marquesa Hotel

Old Town Key West

10/10 Excellent

David

A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

Courtyard by Marriott Key West Waterfront

Northside Resort

10/10 Excellent

Ased

A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

The Laureate Key West

New Town

10/10 Excellent

We stayed two nights in the 3-bedroom suite. Everything, from the moment of arrival, was top rate. The front desk attendant was in contact with me via text to ensure a smooth and efficient check in before arrival and was a great help with local recommendations at check in. Departure took 30 seconds yet the desk attendant took the time to ask how everything was, if I needed anything, wished me well, etc. The suite was beautiful appointed and the furniture very functional and comfortable. Our...

Shannon

An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

H2O Suites - Adults Only

Old Town Key West

10/10 Excellent

My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...

Erin

A pool area with lounge chairs and palm trees.

Santa Maria Suites

Old Town Key West

10/10 Excellent

We stayed here for one night for my husband's 40th birthday. The hotel was aware we were celebrating an occasion and offered complimentary refreshment's in our room. We were able to check on early, got upgraded to pool view and also checked out late! When we arrived we were amazed with how huge the suite was. It was the same size as a condo. The decor was beautiful and the entire place was immaculate, including the outside. What we liked most was how quiet and relaxing the place was (there...

Val

Find out more about Cow Key

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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 Florida Keys Eco - Discovery Center, 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.

Cow Key Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cow Key vacation rentals

1. Aqua Lodges at Hurricane Hole Marina

2. The Grand Cayman | Beautifully Remodeled Key West!

3. Poolside Cottage #412

4. Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!

5. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

6. Poolside Cottage #411

7. Steps from Duval, Pool on Site & Bikes Included!

8. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

9. The Tortuga at Sunrise Suites - Balcony & Pool

10. Waterfront Dock Pool Key West Near Duval

11. Leo's Lodge | Newly Updated!

12. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

13. The Cat Island Suite | Charmingly Renovated w/ Pool

14. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

15. Duval Delight | Recently Remodeled Condo on Duval!

16. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

17. Abbey's Attic - Truman @ Duval | Cozy Getaway in the Heart of Key West

18. Underwater Cabana at Custom House Inn | On Duval!

19. The Saint Kitts Suite | Breathtaking View, Heated Pool

20. Chagall's Corner | Newly Remodeled!

Find vacation rentals that suit your style

Top Cow Key Hotel Reviews

Hampton Inn Key West FL

10/10 Excellent

Find out more about Cow Key

Frequently Asked Questions

Are there vacation rentals in Cow Key?

What are some of the best vacation rentals that Cow Key has to offer?

What can I see and do in Cow Key?

What are vacation rentals like in Cow Key?