Holiday houses in Cow Key

Sea Glass Cottage in Historic Key West

Spend time in beautiful Key West and live like a local in a Conch Home! The Sea Glass Cottage is perfect for groups with 4-6 guests & a furry friend! A fully-renovated 2 bedroom, 2 bath home on the second floor with a queen pull-out sofa. Located in an historic neighborhood in downtown KW near beaches, and parks. Enjoy beautiful foliage on your private porch with seating/ grill. Reserve its sister cottage, the Coral Cottage, to accommodate parties of 8-10 in separate units within the same home.

Stay on Roxie - free transport & snacks, 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. 🛥️🌴🎣

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.

3BR In Resort Village, Pools, Free Kayak & Shuttle

Experience the ultimate KEY WEST VIBE aboard our 3BR/2BA sailboat Located at the luxury Perry Hotel, you’ll enjoy on water living, palm trees, and salty air. Free Perks: Kayak, pools, parking, and free shuttle to Old Town! Full Resort Access: 2 pools & hammock park, 2 restaurants, ice cream shop, private bathhouse & Views of million-dollar yachts Live the island life w full access to all resort amenities. Your tropical escape awaits! This memorable place is anything but ordinary.

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

43' Classic Yacht Views, Pools, Duval Shuttle

Create unforgettable Key West memories while staying on our long time charming liveaboard 43' Trawler. This 2 bedroom 1.5 Bath mini yacht will be the perfect home base for your adventures around town or to just sit and enjoy the incredible views and nature. Being at the award winning Perry Marina gives you all the amenities of a 5 star resort. 2 Pools, 3 Restaurants on site, free shuttle to town, hotel gym, laundry and all the charter and adventure options you could ever ask for.

Penthouse in Paradise

Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.

Oceanview condo w/pool, jacuzzi and tennis court

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 !

Hemingway - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Off the beaten path you will find a unique location and a beach front bungalow with endless unobstructed views of the ocean from every bedroom. Featuring an open family area, full kitchen, deck and its own tiki, excellent for grilling, having a cold drink or just gazing at the ocean.  

Tropical Escape at Sunrise

We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

Tiki Suites ~ Original Tiki ~ Floating Bungalows

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

Paradise found

Located on Stock Island this 3 bedroom home is only 8 minutes from Duval street. Walking distance to several great restaurants. Gated community with a gym and large resort style swimming pool. Queen bedroom on first floor with full bath. Second floor King room with private full bath. 3rd bedroom as two twin beds beds with private full bath.