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

Cow Key Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Cow Key holiday rentals

Front of property

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (194 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is S$369
includes taxes & fees
12 Aug - 13 Aug
Aqua Lodges at Hurricane Hole Marina
Exterior

2. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is S$380
includes taxes & fees
18 Aug - 19 Aug
Island View 1BR Residence With Balcony
Premium bedding, iron/ironing board, free WiFi, individually decorated

3. Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
The price is S$1,403
includes taxes & fees
12 Aug - 13 Aug
Lighthouse Suites Collection
Living area

4. Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
2.0 out of 10, (1 review)
"They did not have a room for me when i arrived. Said there was nothing they could do. I was left stranded and ended up paying twice the price for a worst room which was all I could find."
United States
Paris
The price is S$1,678
includes taxes & fees
12 Aug - 13 Aug
Coconut Mallory Marina and Resort Condo
Exterior

5. Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is S$1,700
includes taxes & fees
13 Aug - 14 Aug
Contra House Key West
Exterior

6. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 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 S$1,250
includes taxes & fees
9 Sept - 10 Sept
Atlantic View Luxury Villa with Pool
1 bedroom

7. Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is S$380
includes taxes & fees
17 Aug - 18 Aug
Resort View 1BR Suite
2 bedrooms

8. 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 S$724
includes taxes & fees
18 Aug - 19 Aug
Grand Marina Suite by Brightwild Waterfront
Exterior

9. The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
9.0 out of 10, Wonderful, (2 reviews)
"A little dated, but clean and well located."
United States
Luis
The price is S$697
includes taxes & fees
8 Sept - 9 Sept
The Grenada Suite Pool View Private Balcony
2 bedrooms, Internet

10. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is S$640
includes taxes & fees
8 Sept - 9 Sept
Tortuga Suite Sparkling Pool Hot Tub
Exterior

11. Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is S$436
includes taxes & fees
16 Aug - 17 Aug
Ocean Front One Bedroom Residence
Exterior

12. 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 S$421
includes taxes & fees
17 Aug - 18 Aug
Resort View 1BR Suite With Direct Pool Access
Exterior

13. Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
"The roosters crowing early morning was irritating "
United States
Catherine
The price is S$658
includes taxes & fees
19 Aug - 20 Aug
Two Bedroom Residence With Balcony
Exterior

14. Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Clean and spacious. Great view from room!"
United States
Jacqueline
The price is S$499
includes taxes & fees
19 Aug - 20 Aug
Ocean Front 1BR Suite With Direct Beach Access
2 bedrooms

15. Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
The price is S$674
includes taxes & fees
16 Aug - 17 Aug
Resort View 2BR Residence
Exterior

16. Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
The price is S$453
includes taxes & fees
17 Aug - 18 Aug
Ocean Front 2BR Residence
Terrace/patio

17. Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is S$538
includes taxes & fees
18 Aug - 19 Aug
Banana Split by Brightwild Pool Grill
Exterior

18. Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
The price is S$1,039
includes taxes & fees
16 Aug - 17 Aug
Resort View 3BR Residence
Garden

19. New The Cottage at James House

New The Cottage at James House
2.0 star property
Key West Historic District
8.0 out of 10, Very good, (2 reviews)
"The best thing about this property is location. Short walk to everything - short walk to Sloppy Joes. It is overpriced for the accommodations but you pay for location. "
United States
Pamela
The price is S$502
includes taxes & fees
17 Aug - 18 Aug
New The Cottage at James House
1 bedroom, Internet

20. The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is S$502
includes taxes & fees
31 Aug - 1 Sept
The Bartlum Luxury Studio In Prime Location
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

Hampton Inn Key West FL

Hampton Inn Key West FL

8/10 Good
"This is a great hotel; offering a beautiful ocean view on S Roosevelt Rd. It has a nice big pool, a tiki bar right by the pool (although there are no waiters coming by to take order - you must go and get it yourself, not a big deal, but it would be nice). The rooms were spacious, comfortable, and most importantly, very clean! Oh and the hotel offers a free shuttle to Downtown every 45mins, so that was awesome. My favorite part was being right across the river ocean sidewalk and taking long walks in the morning. I would recommend giving it a try."
Daniela 4-night trip
Posted 12 hours ago
Hampton Inn Key West FL

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?

Sugarloaf Key RV Resort & Cottages: This holiday home rental outside of Cow Key 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 holiday 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 wider area, you’ll find Duval Street and Robbie's.

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.