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Tropical Heron Hideaway w/ Hot Tub + Pool

Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

Duval Vibes • Pool • 10 Guests

Located only 30 seconds from Duval Street, this house will be your Key West headquarters for bachelor parties, family reunions, or any celebration that bring you to town. This 3 bedroom/ 2.5 bathroom home has a full kitchen, spacious outdoor living space, outdoor shower, private second story sundeck, and a pool. Your group of up to 10 will love being steps away from all KW has to offer- be Hemingway's neighbor! Add this listing to your wishlist by clicking the ♥ in the upper right hand corner.

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. 🛥️🌴🎣

Charming Key West Vacation Rental 3bedrm/3bath

Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler. Portable Crib, high chair & more. Items available upon request

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.

Key West Beach House

Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary in Key West with crystal-clear water views and direct beach access. Enjoy the private beach, furnished with thick-cushioned chairs, picnic tables, barbeque grills and a private dock. Soak up the sun in the zero-entry lagoon shaped pool and hot tub. Walk down stairs and enjoy the complimentary kayaking, gorgeous beach area and pool. Spend a wonderful week in the sunny Florida Keys!

3 Bedroom Home - Perfect Location & Private Pool

The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street and all major attractions. This rental listing includes the second and third floors of the home, which features three bedrooms, a private swimming pool, spacious living areas inside and outside, off-street parking, and a newly renovated chef's kitchen to prepare meals. The first story of the home will be left vacant when this listing is rented.

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

The Historic Family House is decorated in a light, Caribbean motif. It is a Cigar Maker's Cottage from 1880's. 2 K memory foam beds upstairs w/32” Smart TV's, Q sleeper sofa (memory foam mattress) in LR with 75” Smart TV. Bose blue tooth speakers and Alexa's. 1/2 bath up, full bath down plus an outdoor private shower. Full kitchen! Perfect for Families! Private rear deck with new 6 person Jacuzzi. 2 heated pools!

Castaway Cove: Pet-friendly 2/2 condo near beach!

Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.

Tiki Suites ~ Original Tiki ~ Private Water Stay

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.

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Spencer’s boat yard 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