Smoking friendly holiday rentals in Key West

Key West Paradise

Bring the whole family or a great group of friends to this fantastic house w/lots of room for fun. 3 Bed (1 on main level, 2 up), 3 Full Baths (1 on main level, 2 up), sleeper sofa in living room and air mattress in closet, Steps to Community Pool, Sleeps up to 8. Nice Kitchen for your use. High speed internet. TV in the living room and in every bedroom. Enjoy the breeze from your nice size front porch, rear deck off living room, and balcony off upstairs bedroom. 8 minutes to Duval Street.

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. 🛥️🌴🎣

Luxury Waterfront Oasis w Heated Pool and 50' Dock

Have the Florida Keys vacation of your dreams at the luxurious 4Bed 4Bath tropical oasis immersed in a tranquil, friendly oceanfront neighborhood in Marathon, FL. It offers a relaxing getaway minutes from local shops, restaurants, beaches, attractions, landmarks. This lovely Three-floor waterfront Marathon home was designed with relaxation and comfort in mind. With no expenses spared, Vista Del Mar, a luxury waterfront estate, was custom-built for ultimate relaxation in a tropical paradise.

Villa 5087 on Duck Key BOAT SLIP available

Enjoy a Fully Renovated Villa on Duck Key. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors, NO pets. Please do not take any items from the Villa. No pool access

Ocean~View w/ Dock, Pool, Kayaks, King Bed

Experience waterfront luxury in Venture Out on peaceful Cudjoe Key! Enjoy stunning Atlantic Ocean views, amazing sunsets, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Keep your boat at the house and reach the Atlantic or Gulf in minutes. Near Key West, this updated Keys getaway includes resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, especially lobster season in August, so book now!

Seas the Day

7-NIGHT MINIMUM, per Key Colony Beach Ordinance Two bed/two bath half-duplex in Key Colony Beach, known as the "Gem of the Florida Keys." Awesome location! Rental includes free access to Cabana Club, a private club with swimming pool, beach, lounge chairs and ordering options for food and drink. Unit is a 10 min walk to Sunset Pk Beach, great views, no swimming, and nearby restaurants, golf course, tennis courts and playground. Dockage for boats up to 60ft and beautiful water

Just Chillin' Out on the Ocean: 1/2 Off Charters!

Live your dream of sleeping out on on the ocean in a deluxe cabin cruiser yacht. Yacht "Just Chillin" features two state rooms each with comfy queen beds, two full bathrooms, A/C, hot water, high speed internet, covered patio, full dining , kitchen, living rooms and more! The yacht is anchored out on the ocean: see unbelievable waterfront sunsets and wildlife right from the boat! Enjoy this unique experience! All guests receive HALF OFF excursions! Welcome Aboard!

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

Beautiful 42ft Catamaran 1 mile from Duval St.

Escape to paradise aboard our 420 Lagoon, 42' catamaran anchored in turquoise waters off Key West. Recently refit, she offers 3 cozy cabins, 3 baths (two full shower), a well-equipped galley, and full A/C. Sleeps 6 with space to relax inside or on deck under the stars. Sway with gentle waves, watch dolphins swim by, and let island breezes and sunsets make this your private floating getaway in the Keys.

Soothing Nest

Take a break and unwind at this peaceful oasis. Experience Florida's clear blue water and wildlife firsthand while staying in a beautiful home right by the ocean.Resting in peaceful environment that help with sleeping improvement, lowering stress levels and improving general health and welfare is what is offered in this beautiful home.

KW Beach house with heated pool, dock, accessible

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!

Grand Arenas /120'Dock/Mini Golf/HtPool /Game Room

Come stay with us! Here you’ll find it all: a fully renovated home just minutes from the beach, a 124-foot canal ready for your yacht, a heated pool, private mini golf, and a game room full of fun. Sun, sea, and unforgettable memories are waiting for you. Book your stay and start living the Key Colony Beach dream!