Smoking-friendly holiday rentals in Key West

4.75 out of 5 average rating, 128 reviews

An empty gravel lot is showcased, surrounded by lush greenery and palm trees. A picnic table is positioned to one side, providing a space for outdoor dining. The open area suggests ample room for a camper and additional parking.

Campsite in Big Pine Key

Bring Your Own RV! Our Lot Your RV B6 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 ALLOWED2 ANIMAL MAX NO POP UPS / HOMEMADE CAMPERS/SCHOOLBUS OUR BASED ON AIR BNY POLICY AND THEY DO NOT ALLOW ME TO CHANGE THAT

4.87 out of 5 average rating, 82 reviews

A well-maintained community pool is surrounded by lush tropical landscaping, featuring lounge chairs with blue umbrellas. The clear water reflects the bright blue sky and palm trees, creating a relaxing atmosphere for guests to enjoy.

Home 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.

4.9 out of 5 average rating, 227 reviews

A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.

Boat in 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. 🛥️🌴🎣

4.72 out of 5 average rating, 128 reviews

A spacious heated pool is set amidst lush tropical landscaping, featuring palm trees and vibrant greenery. Several lounge chairs line the pool area, and a thatched-roof hut provides additional shade. The scene is enhanced by bright blue skies with scattered clouds.

Townhouse in 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

4.87 out of 5 average rating, 106 reviews

A modern kitchen features stainless steel appliances and white cabinetry, complemented by a light countertop. A dining area and living space are visible in the background, along with a staircase leading to the upper level. Large sliding doors provide access to an outdoor view.

Condo in Duck Key

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

4.71 out of 5 average rating, 14 reviews

Boat in Key West

Resort chic on the water!

Enjoy the sights and sounds of nature while you stay on this 42' roomy sailboat. The cockpit has a small table and is very spacious. There is 6' 8" headroom and lots of light down below. The boat is docked at the Perry Hotel, one of the finest resort locations in the world. There are 2 pools, 3 restaurants and a 24 hour gym on sight. The concierge can arrange trips for you, and a shuttle will take you to downtown every hour until 10:30 pm. The lobby is a great place to relax and mingle.

4.95 out of 5 average rating, 80 reviews

Home in Cudjoe Key

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!

Top Guest favourite

A spacious pool area is surrounded by patio tiles, featuring two green lounge chairs and multiple seating options for relaxation. Palm trees and a canal are visible in the background, enhancing the outdoor ambiance. The clear blue sky reflects a pleasant atmosphere.

4.97 out of 5 average rating, 64 reviews

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

Top Guest favourite

A wooden dock extends into a calm canal, surrounded by clear water. Post lights are visible along the dock, and palm trees line the opposite bank. The sky above is partly cloudy, enhancing the tranquil setting.

Home in Key Colony Beach

4.86 out of 5 average rating, 21 reviews

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

4.94 out of 5 average rating, 161 reviews

A spacious living area features a comfortable futon adorned with a decorative pillow. Large windows provide views of the tranquil water, allowing natural light to brighten the space. The walls are designed in a soft, neutral tone, enhancing the overall welcoming feel.

Houseboat in Key West

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.

4.78 out of 5 average rating, 36 reviews

The yacht 'Just Chillin' is illuminated at night, showcasing its sleek design and multiple levels. Soft light emanates from the upper deck, highlighting the covered patio. Reflections of the boat shimmer on the water, creating a serene nighttime setting.

Boat in Key West

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!

Top Guest favourite

A cozy sleeping area featuring a quilted bedspread in various patterns. A kitchenette with modern appliances is visible, complemented by cabinetry. Two refrigerators are nestled in the corner, and a large mirror reflects the space. Ambient lighting and decorative touches add character.

Houseboat in Marathon

4.93 out of 5 average rating, 45 reviews

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

Popular amenities for Key West Smoke-Friendly Accommodation

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Smoking-friendly apartment rentals

The exterior of Coconut Mallory Resort and Marina is showcased, featuring lush greenery and palm trees. A weathered boat is set in a landscaped area surrounded by stones. A sign displays the name of the resort, adding an inviting touch to the natural surroundings.

Apartment in Key West

Coconut Mallory 2 BD Condo-112

A charming resort building is nestled among palm trees, featuring a light-colored exterior and a welcoming porch. The path is lined with neatly trimmed bushes, leading to the entrance. A sign is visible, indicating a specific unit number.

Apartment in Key West

3.67 out of 5 average rating, 3 reviews

Coconut Mallory 1 BR Condo-404

A comfortable living area features a plush sofa and a small white coffee table. Shelves filled with books stand against the wall, while natural light streams in through large glass doors. Soft lighting is provided by a lamp on the side table.

Apartment in Big Pine Key

Sir David Waterfront

Private room in Big Pine Key

4.6 out of 5 average rating, 15 reviews

Star Room At Barnacle Resort

Apartment in Key West

Coconut Mallory 2 BD Condo-221

Smoke-Friendly Holiday Houses

4.93 out of 5 average rating, 30 reviews

A scenic view of a wide canal is presented, lined with palm trees and residential properties. Boating vessels are seen docked along the sides, with clear blue skies and scattered clouds above, reflecting the relaxed atmosphere of the area.

Home in Key Colony Beach

3/2 Waterfront/Private dock/Beach & Pool Access

Beach House in Marathon with Amazing Backyard!

An aerial view showcases a heated saltwater pool surrounded by lush tropical landscaping. Lounge chairs and a shaded dining area are positioned nearby, while a grill is visible on the patio. The vibrant blues of the pool contrast with the greenery, enhancing the outdoor retreat feel.

Dragonfly Lite

Cozy Beach House in Marathon

4.75 out of 5 average rating, 4 reviews

Blue Paradise Call for Weekend ONLY rates

An outdoor area features a hot tub set among palm trees and a thatched-roof gazebo. Nearby, a round table with a vibrant orange top and metal chairs provide seating. The space is surrounded by scenic water and additional lounge chairs, creating a relaxed environment.

4.93 out of 5 average rating, 14 reviews

Best deals in Duck Key Dream House Jewel!

The exterior of a two-story home is framed by tall palm trees, with shaded parking underneath. A picnic table and a grill are positioned on the ground level, while a balcony overlooks the lush surroundings.

Home in Cudjoe Key

4.71 out of 5 average rating, 83 reviews

Tree Top Paradise

A well-appointed deck overlooks a serene canal, featuring a heated pool and lounge chairs. Lush greenery surrounds the pool area, creating a relaxing atmosphere. Palm trees sway gently in the breeze, with clear skies above, enhancing the tranquil outdoor space.

4.79 out of 5 average rating, 67 reviews

Spacious Marathon FL Pool, Canal front, w/ Kayaks

Smoke-Friendly Holiday Condos

A serene waterfront scene is depicted, showcasing a tranquil bay filled with boats at anchor. Lush palm trees frame the foreground, while several pilings are visible along the water's edge. The clear blue water reflects the sky, contributing to a peaceful atmosphere.

Condo in Marathon

4.56 out of 5 average rating, 9 reviews

OCEAN FRONT /W Pool/Balconies/golf, dock ramp

A view from the balcony showcases a serene ocean scene with gentle waves lapping against the shore. Palm trees sway in the breeze, enhancing the tropical atmosphere. The white railing offers a clear line of sight to the pier extending into the water.

Fabulous Coconut Beach Key West

A resort area is surrounded by palm trees, featuring a large swimming pool and seating areas. Lush greenery and tropical landscaping are visible around the poolside, with lounge chairs positioned under shade. Sunny blue skies create a bright backdrop for the tranquil setting.

Coconut Beach Resort Key West

An entrance to Coconut Mallory Resort and Marina is depicted, featuring a weathered boat partially submerged in lush greenery. The surrounding landscape includes various tropical plants and a sign indicating the resort's name. A multi-story building is visible in the background, surrounded by palm trees.

4.38 out of 5 average rating, 8 reviews

Wahoo Watch Two-Bedroom Condo

A spacious private balcony is visible, featuring a round table with four chairs and several lounge chairs arranged on the concrete surface. The Atlantic Ocean can be seen beyond, framed by palm trees and a clear blue sky with scattered clouds.