Vacation rentals in Cow Key

Amazing 4 Bdrm, 4 Bath Catamaran- Sleeps up to 8

Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom, a full kitchen with everything needed for on board meal prep, spacious living areas down below and above on the decks. The boat is in great condition and has been well maintained inside and out. Purpus is docked in a first class marina with access to free parking, restaurants, bars, ship store, pools, ice cream shop and laundry. Charter options available for additional fee.

Waterfront Boat Stay + Resort Amenities

A Whim isn’t just a place to sleep—it’s permission to unplug and let vacation unfold naturally. Docked at the exclusive Perry Hotel & Marina, this 40-foot, 2-bedroom luxury yacht is tucked away from the crowds, while remaining just minutes from downtown Key West. Featuring inviting indoor and outdoor spaces for living, dining, and relaxing, it offers the perfect balance of comfort and adventure. Guests enjoy hotel amenities, including two pools, a gym, and three waterfront bars and restaurants.

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, & free shuttle to Old Town! Full Resort Access: 2 pools & hammock park, 3 restaurants, ice cream shop, private bathhouse & Views of million-dollar yachts Plz read everything below before booking. I want you to be completely informed about staying on the water. We look forward to hosting you! 🌊💙⚓

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. 🛥️🌴🎣

Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

Newly Renovated 2/2 Bath Condo, with shared pool

Welcome to Poseidon Too! A newly renovated 2/2 bath condo @ Sunrise Suites. Our condo is located 1 mile to the beach, 5 miles to downtown Duval St. With a full renovation just completed from top to bottom, you will enjoy top of the line furniture, furnishings, a brand new kitchen, and private balcony to enjoy amazing sunsets. Things To Note: - Guests will have full access to pool, hot tub, pool towels, gym, & tennis court - Free parking - Keurig and drip coffee - Smart TV's in each room

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.

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 !

Strictly Pleasure | Unique Yacht Stay in the Keys

Staying aboard Strictly Pleasure offers a truly unique Keys experience. Enjoy life on the water with beautiful marina views, sunsets from the bow, and the charm of staying on a classic yacht. Located at Perry Marina, guests have access to pools, waterfront restaurants, and the trolley to downtown Key West. It’s the perfect mix of relaxation, location, and a one-of-a-kind stay you won’t find in a typical hotel.

Beautiful Houseboat in Key West

Enjoy a unique and peaceful stay on our cozy houseboat in Key West. Perfect for couples or small families who want a relaxing water experience close to town. Comfortable sleeping area, deck space, and beautiful sunset views. Check-in is by appointment with personal captain meet-and-greet and boat transfer from the marina. A memorable island stay surrounded by nature and ocean air.

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.