Vacation rentals in Raccoon Key

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.

Casa Calypso 3bed3bath sleeps 8 beautiful decorate

Bring the whole family to this great place with lots of room for fun. Very clean, organized stand alone house with everything you will need to have a great stay! Fully stocked kitchen with a kuerig and drip coffee pot. Can have twin beds downstairs or convert into a king. Two king bedrooms upstairs. Each bedroom has its own bath! A queen sleeper couch in living room with a screen divider for privacy if needed. Steps away from the large heated community pool. Several nice restaurants around.

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.

Cozy Tiny Houseboat: Find Your Peace and Balance

Welcome aboard your cozy houseboat, Balance Key! Perfect for couples, friends, or solo travelers seeking a unique and creative experience that transcends conventional travel. Disconnect from the everyday hustle and bustle and enjoy a refreshing ocean getaway or embark on adventures exploring vibrant marine life, all while taking in 360-degree views through our glass doors whether you’re indoors or outdoors. Two free Kayaks and a dinghy (only for experienced users, $50 one time fee)

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.

Funky Chicken Cottage with Shared Pool in Paradise

Funky Chicken Cottage is a charming and eclectic vacation rental located in Key West, just a short drive away from the main island on Stock Island, Florida. This 3 bedroom, 3 bathroom property is the perfect blend of comfort and style, with unique Martha DePoo art and Cuban art. The highlight of this property is the beautiful pool area, gated community. The property also features two parking spaces under the house, making it convenient for guests who are driving to the island.

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 !

Tropical Heron Hideaway w/ Hot Tub + Pool

Welcome to our charming 1932 Key West retreat in the peaceful Meadows neighborhood. This unique getaway features a private porch, a private hot tub, access to a shared pool and BBQ grill, and all the comforts of home. Blending historic island charm with modern amenities, it’s just minutes from Duval Street, the Historic Seaport, beaches, restaurants, and local attractions—the perfect place to relax and experience authentic Key West.

Wake Up On The Water | Luxury Marina | Key West

Wake up to the rhythm of the water and experience Key West from a completely different perspective. Stay aboard a 45-ft sailing yacht at the Perry Hotel & Marina. Enjoy 2 pools, gym, fine dining, and a free shuttle to Old Town. Ideal for couples or close knit groups: intimate, memorable, and all part of the yacht lifestyle. This boat and the dinghy are not to be turned on. This is a stay at the dock in the marina, no sailing.

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.