Smoking friendly vacation rentals in Summerland Key

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Top-rated smoking friendly rentals in Summerland Key

Guests agree: these smoking friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

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

4.88 out of 5 average rating, 68 reviews

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.

Guest favorite

The exterior of the vacation home is framed by vibrant palm trees, providing a tropical feel. A white staircase leads to the covered front porch, which features a round glass door. Decorative stone landscaping complements the structure, enhancing its inviting appearance.

Home in Cudjoe Key

4.94 out of 5 average rating, 65 reviews

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!!

Guest favorite

The exterior of a two-story house is visible, featuring light-colored siding and a spacious front porch with white railings. A brick driveway leads to the covered parking area underneath. Tropical landscaping with palm trees surrounds the property, enhancing the serene environment.

Home in Marathon

5 out of 5 average rating, 22 reviews

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.

Guest favorite

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

4.91 out of 5 average rating, 200 reviews

Stay on Roxie with FREE anytime cancellation!

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. 🛥️🌴🎣

Guest favorite

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

4.71 out of 5 average rating, 120 reviews

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

Superhost

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

4.86 out of 5 average rating, 99 reviews

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

Superhost

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

4.82 out of 5 average rating, 22 reviews

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!

Superhost

An elevated two-story home is showcased, situated above a spacious patio area. The exterior is adorned with light-colored siding, and a fire pit encircled by stone is visible in the foreground. Lush palm trees add to the tropical ambiance, enhancing the outdoor space.

Home in Marathon

5 out of 5 average rating, 4 reviews

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.

Guest favorite

A spacious concrete dock extends into clear blue waters, featuring thatched-roof palapas for shade. Palm trees sway gently, while colorful buoys line the water. The sky is mostly sunny with a few clouds, enhancing the serene waterfront setting.

Campsite in Cudjoe Key

5 out of 5 average rating, 13 reviews

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.

Guest favorite

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.

Home in Marathon

4.97 out of 5 average rating, 59 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

Guest favorite

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

4.79 out of 5 average rating, 14 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

Superhost

An aerial view of the resort highlights a sparkling swimming pool surrounded by sun loungers and palm trees. A sandy beach area meets the water, with a relaxation gazebo nearby. The expansive ocean sparkles under the sunlight, creating an inviting atmosphere.

Holiday park in Cudjoe Key

"Pirate’s Playground" Venture Out

Welcome to Pirate's Playground at Cudjoe Key, a delightful RV Lot within the renowned Venture Out RV Resort. This gated community spans 69 acres of lush tropical paradise, offering a serene escape on Cudjoe Key, Florida. Just 20 miles from the vibrant Key West, this resort provides exceptional access to both the Atlantic Ocean and the Gulf of Mexico, making it an ideal destination for all your ocean adventures.