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 2/2 1/2- Parking, Bikes, WI-FI, Big Pool

Very clean and spacious, including parking, bikes, wifi, pool and close to many restaurants Luxury 2 /2 1/2 condo sleeping 6 *1100 sq. ft *FREE Covered Parking *7 Bikes FREE - included *Queen bed each room with private bath *FREE wifi *All linens/bath/beach towels included *Huge heated pool *Clubhouse/fitness ctr *Queen sleeper sofa with 5" thick memory foam mattress (very comfortable) *AC *Near many eateries *Coolers *Gas Grill *42" SONY TV -Fire Stick- no cable Maximum 6 person occupancy

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

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 charter guests receive 2-for-1 water shuttles for their stay! Welcome Aboard!

Mermaid Manor ~ Waterfront Haven w/ Hot Tub & Dock

Discover waterfront luxury at Mermaid Manor, a stunning 4BR retreat in Marathon. Built in 2019, this elevated home features power-adjustable Tempur-Pedic beds, 6-person LED-lit spa, and a new 50ft dock with deep water access. Enjoy the outdoor kitchen, cantina bar, paddleboards, and multiple entertainment areas. Perfect for boating enthusiasts with quick access to both Atlantic and Gulf waters. Modern amenities include 500Mbps WiFi, smart TVs, and gourmet kitchen with specialty cookware.

Ocean~View*Pool*Dock*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!

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

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers 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 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.

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.