Smoking friendly holiday rentals in Summerland Key

4.87 out of 5 average rating, 83 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, 235 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. 🛥️🌴🎣

4.87 out of 5 average rating, 108 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.

Apartment 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

4.95 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 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, 22 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

Camper van/Motorhome in Big Pine Key

A gravel pathway leads through lush greenery, with tall palm trees flanking the entrance. The lot is bordered by a variety of tropical plants, creating a secluded atmosphere. The clear blue sky provides a bright backdrop to the natural setting.

4.58 out of 5 average rating, 24 reviews

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

4.81 out of 5 average rating, 43 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

4.95 out of 5 average rating, 57 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

4.85 out of 5 average rating, 34 reviews

Boat in Key West

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.

An outdoor area features a fenced pool surrounded by colorful chairs. Palm trees provide shade, and the spacious deck above is visible. The setting reflects a relaxed atmosphere with nearby greenery enhancing the tranquil environment.

4.85 out of 5 average rating, 26 reviews

Soothing Nest

Take a break and unwind at this peaceful oasis. Experience Florida's clear blue water and wildlife firsthand while staying in a beautiful home right by the ocean.Resting in peaceful environment that help with sleeping improvement, lowering stress levels and improving general health and welfare is what is offered in this beautiful home.

4.85 out of 5 average rating, 13 reviews

Home in Key West

KW Beach house with heated pool, dock, accessible

This is a minimum 28 night minimum rental. Welcome to your dream getaway, just 13 miles from downtown Key West! This charming two-level beach home offers the perfect blend of relaxation, adventure, and luxury. With accommodations for up to 10 guests, bring the entire family, friends, and even your fur babies, and don’t forget your boat!

An aerial view captures the waterfront property with a heated pool and outdoor seating areas, surrounded by lush palm trees. The private canal is visible, along with neighboring homes. Blue skies enhance the tropical setting, creating a serene atmosphere perfect for relaxation.

4.92 out of 5 average rating, 25 reviews

Grand Arenas/120'Dock/Mini Golf/HtPool/Game Room

Come stay with us! Here you’ll find it all: a fully renovated home just minutes from the beach, a 124-foot canal ready for your yacht, a heated pool, private mini golf, and a game room full of fun. Sun, sea, and unforgettable memories are waiting for you. Book your stay and start living the Key Colony Beach dream!

Popular amenities for smoke-friendly rentals in Summerland Key

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Smoke-friendly flat 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.

Flat 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.

Flat 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.

Flat in Big Pine Key

Sir David Waterfront

Private room in Big Pine Key

4.67 out of 5 average rating, 18 reviews

Star Room At Barnacle Resort

Flat in Key West

Coconut Mallory 2 BD Condo-221

Smoke-friendly house rentals

4.94 out of 5 average rating, 31 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

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

4.86 out of 5 average rating, 7 reviews

Blue Paradise Call for Weekend ONLY rates

Top guest favourite

The tranquil scene features a waterfront property with multiple levels, complemented by a wooden dock. An American flag gently flutters in the breeze. Sun loungers and colorful kayaks are visible along the shoreline, with clear blue skies reflecting on calm waters.

4.96 out of 5 average rating, 25 reviews

Luxury Waterfront Oasis w Heated Pool and 50' Dock

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

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

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.

5 out of 5 average rating, 11 reviews

Mermaid Manor ~ Waterfront Haven w/ Hot Tub & Dock

Smoke-friendly apartment rentals

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.

Apartment 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.

5 out of 5 average rating, 3 reviews

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.

4.58 out of 5 average rating, 12 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.