Holiday houses in Rockland Key

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 ice-cold AC, palm trees, and salty air. Free Perks: Kayak, pools, parking, and free shuttle to Old Town! Full Resort Access: 2 sparkling 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.

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.

Oceanfront Cottage with Open Water Views

Oceanviev Serenity provides stunning open water views, and a 60 foot seawall for your boat. Comes with paddle board, kayaks, and more. Newly renovated 2BR cottage sleeps MAXIMUM OF FOUR (4) GUESTS, with a King in the Master BR and one Queen size bed Guest BR (both with new JW Marriott mattresses for comfort). All new appliances! Enjoy resort amenities like a pool, hot tub, tennis, and marina store. Just 30 minutes from Key West. $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON).

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!

Luxury 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 ft 2-bed luxury boat with island bright touches is tucked away from the crowds in a resort style marina while being just minutes from downtown Key West. Featuring indoor and outdoor spaces for living, dining, and relaxing, as well as hotel amenities such as a pool, 3 bars and restaurants, and a gym. Vacation differently on A Whim.

The Lighthouse - Beach Houses Key West

If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

b watervibe

Disfruta de los sonidos de la naturaleza cuando te quedes en este lugar único. Es algo diferente para disfrutar con tu pareja de un momento romántico y divertido y así relajarse y olvidarse de la vida cotidiana. Puedes disfrutar de la pesca ,de paseos en kayak ,vivir una aventura y disfrutar de otras actividades locales.Prueba de la expericiensa y ya ustedes diran.Esta casa flotante ofrece un espacio para 2 adultos. Está Esta es una experiencia de Acampada .

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.

Exceptional Water View With Boat Dock!

This is the best kept secret. 10 miles from Duval St. for the night life, but a total private oasis if you are looking for a true get away. This is an end unit with a water view from every window in a gated community with a salt water pool. Wake up to an ocean view and have cocktails on the patio. This is a brand unit that has recently been completely renovated.

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.

Oceanfront, beach, heated pool, dock, tiki hut

This is a minimum 28 night minimum rental. Welcome to your dream getaway, just 13 miles from downtown Key West! This charming two-level beach home offers the perfect blend of relaxation, adventure, and luxury. With accommodations for up to 10 guests, bring the entire family, friends, and even your fur babies, and don’t forget your boat!