Holiday rentals in Cow Key

Stay on Roxie - free transport, snacks & ice. BYOB

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

Sailboat Stay + Resort Amenities

Unplug and unwind aboard The Dream, your own sailboat in Key West, Florida! This is not your typical Airbnb — it's a floating escape on a beautiful 1-bedroom, 2-bathroom 42 foot sailboat docked at the exclusive Perry Hotel & Marina (just minutes from downtown!) Enjoy a queen bed in the spacious Captain’s suite, 2 full-sized paddle boards, snorkel gear, private Wi-Fi, and more. With tropical vibes, luxury touches, and the comforts of home, this is where island adventure meets peaceful retreat.

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

A Great Escape! Private 2 Bed Rm Beautiful Marina

Our Marina has a pool and a small private beach overlooking the beautiful Keys water! More affordable than most places in Key West while able to reconnect with nature at this private getaway on the Great Escape. As you approach the boat, you feel your dream vacation has come true . One of a lifetime. Staying on a beautiful sportfisher yacht, laying in the waters of the calm keys and in the most beautiful peaceful marina, will definitely set you free from all your worries and stress.

Elegant Sailboat Stay

Nestle into comfort and embrace the charm of this Hunter 380 Sailboat , on waters edge at the Perry Hotel and Marina! This unique sailboat getaway offers a perfect blend of tranquility and adventure, providing an unforgettable escape for both relaxation and exploration enthusiasts. As a guest on Susquehanna you will be entitled to enjoy all the marina and hotel facilities including 2 pools , full gymnasium and regular free shuttle buses into the Old Town of Key West (15 minute ride)

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Great Ocean Views! No regrets

Your Ocean front vacation house on water awaits you! Experience Key West staying above it's beautiful clear water. There is a little something for everyone from adventure seekers, to people who just want to get away and enjoy island life. You will see all kinds of sea life including a manatee from time to time! From deck view gorgeous sunsets, various sea birds catching their meals and even a military jet formation on occasion. Many great areas to kayak/paddle board off the boa.

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

Oceanview condo w/pool, jacuzzi

Plan your next vacation at this peaceful, breathtaking, Ocean-view condo at La Brisa resort located across the street from largest beach on the island, Smathers Beach. Take advantage of the pool, tennis courts, hot tub, and sauna or just enjoy the Atlantic Ocean view from your private balcony. The condo is in a gated community with private parking and elevator access. Bring your family and lets enjoy your vacation in Key West 🌴☀️ No pets allowed !

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

Airstream Key/RV rental&delivery, campsite require

We will DELIVER and SET UP our Airstream to your favorite campsite. Simply book your campsite and then book with us. We will have everything ready at your arrival. Check in and out times are up to the campground. Our outdoor pictures were at the Boyd’s Key West Campground. Start your next adventure in the Key West and step into the uniquely designed Airstream RV where you'll feel sassy and classy!

Hyatt Beach House-Quiet Key West Spot!

Located 2.7 miles from Smathers Beach and 3.8 miles from the Ernest Hemingway Home & Museum, this quiet piece of Key West is the best location for relaxation. The property is on a corner of the island featuring its own private beach and water access. Other activities in the area include scuba diving, snorkeling, parasailing, fishing, dolphin watching, and boating.