Smoking friendly vacation rentals in Big Pine Key

Paradise At Sunset

Paradise at Sunset is your ideal vacation get-away. Located near the 7-mile bridge where you can catch the sunset or the sunrise! A private pool to enjoy with family and friends, plenty of outdoor seating areas. If you’re looking for places to dine in, The Sunset Grille & Raw Barn is just a 3-minute walk. The Marketplace at Isla Bella is also a unique mix of goods where you can find gifts, coffee, pastries, beach/swim ware. 5 minute drive to Sombrero or Coco plum beach. 45 minutes to Key West.

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. 🛥️🌴🎣

Amazing Ocean views, 35’ Seawall, Kayaks, Bikes

Your perfect Keys getaway in Venture Out on peaceful Cudjoe Key! * Amazing Atlantic Ocean views * 30 Minutes to Key West & Marathon * 35’ seawall on deep water canal * Fish cleaning station & bait freezer * Kayaks, outdoor shower, bikes Keep your boat in the water at your house and be fishing or lobstering on the Atlantic or Gulf in minutes! Our guests get access to Venture Out’s huge pool, pickleball courts, hottub, boat launch, fuel dock and store. We fill up fast… book your dates now!

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

Sailfish Dream on Cudjoe Key-28 day minimum

Sailfish Dream is your keys getaway to indulge in the keys lifestyle. Located at MM 23. For boating enjoy deep channels, quick access to all waterways, Looe Key 20 min by boat. Explore islands bordering channel to Gulf. This 2nd floor home has lots of natural light, vaulted ceiling, plenty of parking, 75 ft of seawall, wrap around balcony, swim in canal, sleeps 6 people. This 2 bed/2 bath home is family friendly for wonderful memories to be made. We are working with a 28 day minimum.

Little Palm By The Sea- RV Site, Cudjoe Key Fl.

Canal front RV LOT 35' x 70' with a 35 ft. seawall for your boat, ocean views and direct access. Fits up to a 45 ft RV. Water, sewer and electric hook up . Beautiful landscaped waterfront site in Venture Out Cudjoe Key Fl., 25 miles to Key West. The site includes a concrete picnic table, boat slip and a swim ladder. Venture Out is a gated community with 24 hr. security on the shores of Cudjoe Key. PLEASE READ the details below for vehicle requirements. Only approved RVs are permitted.

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Garrison Bight Marina in 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 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Paradise Ocean Front 4/3Home Heated Pool

Paradise home only 4 houses from open ocean on the Atlantic side of Marathon with a Pool to soak in.This cozy home features 4/3 open floor plan style living room and kitchen and stainless steel appliances. There's a beautiful tiki hut to relax and cook your fresh catch on the BBQ while looking at the Atlantic ocean. 80 feet of dock space to park your boat or boats and a convenient fish cleaning station with t-top clean and prepare your fresh catch. RENTAL LICENSE ID # PLR2019-00144

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

Bring your own RV. Our lot your Camper B5 No Tents

MUST BRING YOUR OWN CAMPER! 50 amp and 30 amp new electric sewer and water, TAKE ADVANTAGE OF A GREAT LOT FOR YOUR CAMPER Twenty nine miles to key west 1/4 mile to water access. HAS POOL Boondocks Restaurant 1 mile and Bucktooth Rooster walking distance. Only Miniature golf in the keys 1 mile away. Key West 25 minute drive. OUR LOT BRING YOUR OWN CAMPER NO TENTS ALLOWED SORRY 2 ANIMAL MAX NO POP UPS /HOMEMADE CAMPERS/SCHOOL BUS REFUNDS ARE-BASED ON AIRBNB POLICY

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