Vacation rentals in Looe Key

Stay on Roxie with FREE anytime cancellation!

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. 🛥️🌴🎣

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Romantic cozy peaceful Guesthouse beach Sunsets.

Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

Perfect Miami Beach Stay - King Studio

Spacious king studio at Hotel Trouvail Miami Beach, just one block from the ocean in the stylish Faena District. Upgrade your stay with a king bed, sitting area, walk-in rain shower, flat-screen TV and kitchenette with microwave and mini fridge. Enjoy food, coffee, or cocktails at the café, bar, or pool. Nestled in a quiet area that’s still steps from South Beach’s best dining, shopping, and nightlife—but not the noise, traffic, and crowds. Ideal for a relaxing stay or work trip.

Oasis2 in Key Largo With a million dollar view

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

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!

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Keys Fall Escape: Pool, Marina & Tiki Bar

Celebrate the season in paradise at THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, accommodating up to 4 guests. Featuring a complete kitchen, balcony, and access to resort amenities including a pool, Tiki Bar, restaurant, Marina, and more! Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!