Vacation rentals in Cow Key

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Top-rated vacation rentals in Cow Key

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Guest favorite

Home in Key West

4.94 out of 5 average rating, 271 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Apr 21 – 28

ﺩ.ﺇ2,052 per night

Guest favorite

Houseboat in Key West

4.83 out of 5 average rating, 12 reviews

The simple life on Seaplicity!

Come stay on our beautiful & Super Comfy 38 ft Hunter Sailboat at the Perry Hotel & Marina! Start your morning with a fresh cup of coffee on board & "SIMPLIFY" your vacation with unrestricted access to all resort amenities! Two heated salt water pools, gym, laundry, and bathrooms and try one of the great restaurants onsite. Also, you can cook your own meal in the fully equipped galley! Shuttle service takes you to old town Key West! Ask about adding a Captained Sailing Adventure to your trip!

Dec 1 – 8

ﺩ.ﺇ1,060 per night

Guest favorite

Apartment in Key West

4.98 out of 5 average rating, 449 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

Apr 14 – 21

ﺩ.ﺇ1,247 per night

Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

May 5 – 12

ﺩ.ﺇ798 per night

Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 89 reviews

Breezy pines 28 foot 5th wheel trailer .

Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.

Nov 12 – 19

ﺩ.ﺇ398 per night

Guest favorite

Townhouse in Key West

4.87 out of 5 average rating, 174 reviews

*Sparkling new kitchen* 3 bedroom/3 bath home.

Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and two queen beds. The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer installed. The salt water pool is perfect for lazing away your days. There is on street parking for two cars. The center of town is ten minutes away. An entire home for the price of one hotel room.

Sep 26 – Oct 3

ﺩ.ﺇ1,721 per night

Superhost

Houseboat in Key West

4.81 out of 5 average rating, 253 reviews

Key West Houseboat Paradise

56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats. The property has an fairly industrial feel to it with a 2-bay local garage/taxi company on site so Shore Side is nuthin' fancy but the back deck looks out on mangrove islands dotting Boca Chica Channel with two 12' Sea Kayaks ready to go.

Aug 25 – Sep 1

ﺩ.ﺇ1,426 per night

Guest favorite

Boat in Key West

4.93 out of 5 average rating, 42 reviews

Sailboat in Luxury Marina

You will have an unforgettable experience staying on Allora, a 41 ft. sailboat, docked at the Perry Hotel and Marine - a luxury marina. PLEASE VIEW VIDEO BEFORE BOOKING: search "Allora walk through" on youtube Wake up to a freshly brewed cup of coffee and sit in the cockpit watching the sun rise across the water. Swim in the 2 heated, salt water pools and try out one of the many first class restaurants on site. Be sure to take advantage of the free shuttle to old town Key West.

Jun 2 – 9

ﺩ.ﺇ528 per night

Guest favorite

Guesthouse in Key West

4.93 out of 5 average rating, 527 reviews

Old Town - Room Opens to Pool and Garden

Located in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Jun 8 – 15

ﺩ.ﺇ1,240 per night

Guest favorite

Townhouse in Key West

4.91 out of 5 average rating, 109 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Dec 17 – 24

ﺩ.ﺇ1,569 per night

Guest favorite

Apartment in Key West

4.92 out of 5 average rating, 1034 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Sep 18 – 25

ﺩ.ﺇ1,053 per night

Guest favorite

Apartment in Key West

4.97 out of 5 average rating, 236 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

Sep 25 – Oct 2

ﺩ.ﺇ1,209 per night