Holiday rentals with an EV charger in Stock Island

A spacious pool area is surrounded by lush tropical landscaping, featuring a large swimming pool adorned with colorful floaties. Comfortable lounge chairs are placed nearby under shaded umbrellas, offering a relaxing spot to enjoy the outdoors. The scene is framed by palm trees and greenery.

4.99 out of 5 average rating, 70 reviews

Cathouse Old Town Oasis Huge Heated Pool & Parking

Relax in a tropical 3-level townhouse in the heart of Key West hosted by Nautipussy! Perfect for up to 12 guests. This private, gated retreat features private balconies overlooking a stunning shared seasonally heated pool and tiki bars. Ideal for large families or groups, bachelor/bachelorette parties, it's just a short walk to Duval Street and the beach. Enjoy a lush garden oasis with unparalleled privacy and comfort in a vibrant neighborhood. As a guest favorite please read our 5 star reviews.

4.97 out of 5 average rating, 298 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

Tiny home in Big Pine Key

4.82 out of 5 average rating, 243 reviews

Tiny House | 35 min to KW + Free Parking & Pool

Discover a hidden gem in the Florida Keys with this charming Tiny House, surrounded by nature and the famous Key Deer. Located in the peaceful Breezy Pine RV Resort, it offers a cozy yet spacious layout for the whole family. Relax outdoors on the private patio with sofa and grill, perfect for enjoying the laid-back Keys lifestyle. With all the essentials for comfort and just a short drive to Key West, Bahia Honda beaches, shops and restaurants. This retreat is ideal for relaxation and fun.

4.78 out of 5 average rating, 23 reviews

A wooden bridge leads through a lush garden, framed by greenery and festive decorations. A stone wall is visible at the end of the path, flanked by potted plants. Light filters softly through the nearby trees, creating a serene and inviting entryway.

Townhouse in Key West

Hemingway First Floor Townhouse @ Suite Dreams Inn

Suite Dreams Inn is an intimate family-owned boutique Key West Bed & Breakfast in the tranquil upscale Casa Marina Old Town neighborhood, offering oversized suites with luxurious king & queen beds, kitchens, living rooms, 2 pools, 24/7 laundry, free parking, and relaxing outdoor spaces. We are LGTB & pet friendly & will accommodate well behaved children of any age, as well as private clothing optional & traditional guests. Close to the beach, Duval St, jet ski re

4.8 out of 5 average rating, 69 reviews

A serene view of the canal is presented, featuring calm emerald waters under a clear blue sky. Surrounding structures include residences and docks. A boat is visible on the water, along with two boats secured to the dock, highlighting the tranquil coastal setting.

Home in Cudjoe Key

Keys Cove-

Our Keys Cove is a high-rise home with magnificent ocean views. It is located in a fabulous resort community 23 miles from Key West. Our oversized "Parrots Perch" offers a stunning sunrise and sunset experience. Dock your boat on our 43-foot seawall equipped with padded posts and whips. Enjoy the resort amenities including pickleball tennis courts, a huge pool, hot tub, marina, tiki beach, kayaking, and more. Be sure to read our guidebook for the best places to see.

Boat in Key West

New place to stay

Key West • The Harbor House • Luxury Sea Charters

Harbor House Welcome to a completely different way to stay in Key West. This hybrid boat + house experience blends the comfort of a waterfront home with the unmistakable energy of being on the water. This isn’t a cruise. This isn’t a typical rental. This is dockside luxury. Set directly on the water and connected to the Luxury Sea Charters fleet, this is your dockside escape with the option to turn your stay into a full on-the-water experience.

An aerial view of Beachside Resort reveals spacious grounds set against the Gulf of Mexico. The property features multiple buildings arranged around a resort pool, surrounded by lush greenery and access to the marina, highlighting the serene waterfront location.

4.78 out of 5 average rating, 87 reviews

One Bedroom Suite | Beachside Resort

Experience luxury at Beachside Resort, set on seven acres of property overlooking the Gulf of Mexico. Unwind in the perfect blend of adventure and relaxation in sunny Key West. On property, you can find access to our resort pool, ocean marina, and the ability to book a sandbar or sunset cruise. Don’t miss out on fine dining at our award winning restaurant, Tavern N Town, or grab a delectable meal poolside at Chicken Walk.

An open-concept living area features light blue walls and large mirrors that enhance the natural light. Coastal-chic furniture includes a sectional sofa and a round dining table for four. Sliding glass doors open to a balcony, offering views of the surrounding landscape.

4 out of 5 average rating, 4 reviews

Serenity by the Sea | La Brisa

Welcome to your island escape! This 2BR/2BA condo in the gated La Brisa complex is across from Smathers Beach and just a short ride to Duval Street. Enjoy an open-concept layout, coastal-chic décor, full kitchen, private balcony with salt pond views, and resort-style amenities including a 24-hr pool, hot tub, sauna, tennis, EV charging, and more. Perfect for beach days or exploring Key West—book your stay today!

A person is seen on the boat deck, raising a pirate flag. The background features calm waters and distant boats. Cushions and clothing are scattered on the deck, while the blue canopy provides shade from the sunlight.

Boat in Stock Island

AHOY & Welcome Aboard

VERY QUIET LOCATION AS YOU STAY ABOARD A SAIL BOAT- -SEA BREEZES, SOLITUDE, gentle waves or none mostly. as are Coco Row dead end & Iis way quiet here, how do I most of Key West --sounds will be from the zillions of stars, twinkeling & as Caribbean Sea gently rocks you asleep "SAILBOATS Docked@Key West! Amenities-RENT BOTH & KIDS & Adults close but seadults 2nd BOAT adjacent same dock--in OWN BO

Private room in Big Pine Key

Treehouse Private Village Barnacle Resort

Welcome to Barnacle Resort, your seaside sanctuary where luxury, comfort, and adventure blend perfectly. This beachfront retreat offers plush rooms with ocean views, a private beach. For those seeking adventure, complimentary kayaks and bicycles are at your disposal. Here, you'll wake up to the sound of waves, and explore the coastal beauty, feeling like a million bucks each day.

The modern building is designed with balconies overlooking a serene pool area. A turquoise pool is bordered by lounge chairs and palm trees, creating a refreshing outdoor space. The backdrop features a clear sky and a sandy waterfront, enhancing the tranquil ambiance.

4.92 out of 5 average rating, 39 reviews

Oceanfront Condo in Key West, FL

Key West Beach Club is a serene waterfront oasis located in an upscale gated community within walking or biking distance to the local’s finest spots, including restaurants, beaches, shopping centers, bars and the infamous Duval Street. This complex prides itself for being one of the very few on the island that sits directly on the water.

A cozy bedroom features a spacious bed dressed in white linens and decorative pillows. Natural light filters through a window adorned with wooden blinds. A mirror and wicker accents complement the tropical wall decor, while dark hardwood flooring adds warmth to the space.

4.96 out of 5 average rating, 127 reviews

Duval Street Suites full kitchen, free parking, he

Paradise Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic Old Town, Key West. Free parking available and the pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.

Popular amenities for EV charger rentals in Stock Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with an EV charging station

A light-filled living space features a teal sleeper sofa and a small dining table with two white chairs. A textured area rug adds warmth to the wood floor. Decorative wall art and a ceiling fan enhance the relaxed atmosphere.

4.93 out of 5 average rating, 135 reviews

Duval Street Suites full kitchen, free parking, &

A private courtyard is displayed, featuring a hot tub, two chairs, and a small table. The entrance to the suite is visible with elegant French doors that open to the interior. Lush greenery enhances the tranquil ambiance, with a striped awning offering partial shade.

4.92 out of 5 average rating, 317 reviews

Starr's Suite - 2 person K Suite w/Private Spa!

A spacious bedroom features a king bed topped with a vibrant floral duvet and decorative pillows. Light green walls complement wood accents. Two windows with blinds provide natural light, while bedside lamps add soft illumination. A rolled towel is neatly placed on the bed.

4.86 out of 5 average rating, 37 reviews

Historic Old Town Two Duval Street Suites w heated

The entrance to a charming village is marked by an archway adorned with colorful lettering and a distinctive emblem. Lush palm trees line the quiet street, which is paved with bricks, and features colorful buildings along either side.

4.92 out of 5 average rating, 167 reviews

Duval Street Suites with full kitchen heated pool,

A balcony is visible amongst lush green foliage, featuring wooden railings and an overhanging roof. Light filters through the leaves, creating a serene atmosphere that highlights the natural surroundings of the building.

4.55 out of 5 average rating, 11 reviews

Key West Treehouse Duplex Suite @ Suite Dreams Inn

A decorative wooden sign is mounted on a white post, featuring the text 'Center Court Historic Inn & Cottages' in bold letters. Lush tropical greenery surrounds the area, with palm trees and vibrant plants visible, creating a welcoming entrance to the property.

4.95 out of 5 average rating, 348 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

A spacious resort pool is surrounded by palm trees, offering views of the beach in the distance. Lounge chairs are neatly arranged around the pool area, creating an inviting space for relaxation. Clear blue skies enhance the vibrant atmosphere.

4.49 out of 5 average rating, 63 reviews

Double Signature

A resort-style pool is framed by palm trees, with inviting lounge chairs arranged on either side. The clear water reflects the blue sky, while the beach and ocean can be seen in the background, providing a serene setting for relaxation.

4.62 out of 5 average rating, 316 reviews

Signature King

House rentals with an EV charging station

A serene pool area is surrounded by tropical plants and palm trees. Comfortable lounge chairs are positioned near the clear water of the pool. A shaded outdoor dining table with chairs sits on a wooden deck, enhancing the inviting atmosphere of this private space.

4.91 out of 5 average rating, 23 reviews

Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

4.95 out of 5 average rating, 383 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

A welcoming sign for Center Court is prominently displayed, surrounded by lush tropical foliage. The structure features white wooden details, with the sign's text clearly visible in a stylish font. The bright blue sky peeks through the greenery, enhancing the serene atmosphere.

4.96 out of 5 average rating, 242 reviews

Lennon's Lodge, Luxury Accommodations for up to 6!

A charming cottage entrance is framed by lush tropical vegetation, including palm leaves and colorful plants. A small heated jacuzzi is visible beside the brick pathway leading to a light blue door with white trim. Two rocking chairs sit on the welcoming porch.

4.78 out of 5 average rating, 67 reviews

Historic Key West - Cigar House - Sleeps 4

The exterior of the historic cottage is shown, featuring light blue shutters and a welcoming front door. Lush tropical plants and vibrant flowers enhance the front garden. A covered porch with decorative railing offers a charming touch, inviting visitors to enjoy the serene surroundings.

4.92 out of 5 average rating, 318 reviews

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

A wooden sign with the name 'Center Court' is prominently displayed, surrounded by lush tropical foliage. The sign features a decorative design and is mounted on a white post, indicating the location of the historic inn and cottages.

4.91 out of 5 average rating, 239 reviews

McCartney's Manor - Deluxe K Suite W/Pvt. Spa!

Apartment rentals with an EV charging station

A cozy room features mid-century style furnishings, including two blue velvet chairs adjacent to a small dining table. A queen murphy bed is visible in the background, alongside a television mounted on the wall. Natural light enters through the window, highlighting the vibrant yellow walls.

4.92 out of 5 average rating, 106 reviews

Duval Street Suites on Duval Free Parking and heat

A view of a serene waterfront area featuring a wooden dock that extends into the calm water. Lush palm trees frame the scene, while a sandy beach area is visible in the foreground. The clear blue sky complements the tranquil environment.

4.84 out of 5 average rating, 58 reviews

Ocean Front Suite | Beachside Resort

A serene waterfront view features the Gulf of Mexico under a colorful sunset, framed by palm trees. A dock stretches into the water, and lounge chairs line the shore, creating a calming atmosphere for relaxation.

4.86 out of 5 average rating, 22 reviews

Ocean Front Two Bedroom Residence

A private balcony features a view of the Gulf of Mexico, showcasing palm trees and a calm waterway. Boats can be seen in the distance, with a marina visible along the shoreline. The clear blue sky enhances the serene atmosphere.

4.67 out of 5 average rating, 106 reviews

Ocean Front Presidential Suite | Beachside Resort

A tranquil resort pool is framed by palm trees with lounge chairs positioned along its perimeter. The gentle waves of the Gulf of Mexico are visible in the background, complementing the vibrant sunset sky filled with soft pink and purple hues.

4.72 out of 5 average rating, 134 reviews

Two Bedroom Residence

A resort-style pool is surrounded by palm trees and lounge chairs, offering a tranquil atmosphere. The clear blue water reflects the sunny sky, leading to a view of the beachfront in the background. Umbrellas provide shade for relaxation beside the pool area.

4.57 out of 5 average rating, 23 reviews

Pool View Two Bedroom Residence

A private balcony overlooks the resort pool and lush palm trees, providing a serene outdoor space. Two lounge chairs are positioned for comfort, with a ceiling fan offering a gentle breeze under the clear sky.

4.72 out of 5 average rating, 163 reviews

Pool View 3BR Residence | Beachside Resort

A view of the resort pool area is framed by lush palm trees and greenery. Loungers are positioned around the pool, inviting relaxation. The scene is brightened by clear blue skies, creating an atmosphere of leisure and tranquility.