Smoking-friendly holiday rentals in Key West

Private Ocean Oasis by Key West, Florida

Beautiful stilted two bedroom/two bathroom vacation home awaits your arrival. Break taking views of the Atlantic Ocean are picture worthy. This home hosts a 36' seawall on a wide canal. Dock equipped with fishing cleaning station, cleats, swim ladder, outdoor shower and bait freezer. King-, queen-, full- and twin-size mattresses provide comfortable sleeping accommodations for all guests. Extensive indoor and outdoor furniture allow for all to relax, recharge and enjoy their time in paradise!!

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.

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

Yacht Just Chillin': Anchored Out on the Ocean!

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.

Amazing houseboat with a sunset eco-trip included

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.

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

Stay on the Roxie!

Enjoy, peaceful, ocean-breezy, star-filled nights, on the water! Free parking and free round trip transport 1 to & 1 from Roxie per night’s stay! Roxie is anchored in a protected, shallow 3-4ft lagoon. We live on a boat a half-mile away should you need anything. 😊 Roxie has a Keurig, snacks like chips, breakfast muffins or donuts , Keurig pods, bread, peanut butter and jelly, and bottled waters. No cooking but you may bring to go food, drinks. 🛥️🌴

Beautiful 45ft sailboat. 1 mile from Duval St.

Escape to paradise aboard our 45’ GulfStar Sloop, anchored in turquoise waters off Key West. Recently refit, she offers 2 cozy cabins, 2 baths (one with full shower), a well-equipped galley, and full A/C. Sleeps 4 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.