Holiday rentals with a fire pit in Key West

4.98 out of 5 average rating, 50 reviews

Grouper Getaway @ Ocean Isles Fishing Village

Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautiful brand new fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic Ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.

5 out of 5 average rating, 13 reviews

An open-concept living area features wraparound seating in dark leather surrounding a polished wooden dining table. Abundant natural light filters through panoramic windows, reflecting off the rich wooden flooring. Tropical-themed wall decor and greenery enhance the inviting aesthetic. A well-equipped kitchen is visible in the background.

Boat in Key West

Sailboat Stay + Resort Amenities

Unplug and unwind aboard The Dream, your own sailboat in Key West, Florida! This is not your typical Airbnb — it's a floating escape on a beautiful 1-bedroom, 2-bathroom 42 foot sailboat docked at the exclusive Perry Hotel & Marina (just minutes from downtown!) Enjoy a queen bed in the spacious Captain’s suite, 2 full-sized paddle boards, snorkel gear, private Wi-Fi, and more. With tropical vibes, luxury touches, and the comforts of home, this is where island adventure meets peaceful retreat.

4.92 out of 5 average rating, 78 reviews

A spacious living area features a comfortable blue sofa and a white coffee table at its center. Modern appliances are visible in the adjacent kitchen, along with a dining area. Natural light flows in through sliding doors leading to the outdoor space.

Holiday home in Marathon

Perfect Paradise

Perfect paradise is located in the heart of marathon. Only 9 minutes away from sombrero beach. Restaurant, supermarkets, ice cream, aquarium, and much more less than 7 minutes away. Public boat ramp is 5 minutes away. The house has plenty of parking spaces in the front to park your boat and cars. The home is fully stocked with everything you will need during your stay. For specific dates please message me first before booking so I may accommodate you to the dates that you would like to book.

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.

4.95 out of 5 average rating, 21 reviews

Luxury Waterfront Oasis w Heated Pool and 50' Dock

Have the Florida Keys vacation of your dreams at the luxurious 4Bed 4Bath tropical oasis immersed in a tranquil, friendly oceanfront neighborhood in Marathon, FL. It offers a relaxing getaway minutes from local shops, restaurants, beaches, attractions, landmarks. This lovely Three-floor waterfront Marathon home was designed with relaxation and comfort in mind. With no expenses spared, Vista Del Mar, a luxury waterfront estate, was custom-built for ultimate relaxation in a tropical paradise.

4.99 out of 5 average rating, 108 reviews

A backyard area features white sand, surrounding palm trees, and a tall American flag. The A-frame house is visible in the background, complemented by a wooden dock leading to the water. Lounge chairs are arranged neatly, enhancing the outdoor space's appeal.

Home in Key Colony Beach

ABeachBungalow-60’dock w/ access to pool and beach

"A Beach Bungalow" A-frame has everything you need for a relaxing vacation. 2 bedroom, 2 bath Key Colony Beach rental home with easy ocean access. Fully equipped kitchen with all new appliances. Living room with dining area, flat screen tv, wifi, cable, bbq and beautiful views of the water. Master bedroom with king bed and bathroom with large shower. 2nd bedroom (loft) with 2 twin beds and closet. Tackle room to store gear with extra refrigerator. Boat trailer parking on site.

The spacious canal-front home is showcased from an aerial view, highlighting its private pool and lush palm trees. A dock with boat access extends into the water, while comfortable outdoor seating is positioned nearby, creating a relaxed atmosphere for guests.

5 out of 5 average rating, 28 reviews

Spacious lux home, private pool/spa, 80' dock

Sunchasers Paradise has everything you are looking for and more in a spacious canal-front home. It's the perfect place to have your next company or couples retreat or reconnect with extended family. Play and relax in the private pool or spa under the palms swaying in the costal breeze. Sunchasers Paradise is the ideal spot for fishing, watersports, and beach lovers. Enjoy this luxury home with endless amenities, nearby dining, and day trip adventures. Unforgettable moments await!

4.87 out of 5 average rating, 116 reviews

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

Home in Cudjoe Key

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

4.9 out of 5 average rating, 10 reviews

A 40-foot catamaran is anchored in clear turquoise waters. Two individuals are enjoying the ocean; one is swimming while another relaxes on the deck. The yacht features a modern design with a spacious deck for sunbathing and enjoying the surrounding scenery.

Boat in Key West

Luxurious 40' Sailing Yacht!

Enjoy exclusive use of this 40-foot yacht all to yourselves, with the opportunity to get close to ocean life. This yacht is docked at the Perry Hotel & Marina, with free access to two stunning waterfront swimming pools, live music, three restaurants, complimentary shuttle service, & more. Come and go on the yacht anytime, day or night. Participating in an ocean excursion on this yacht is mandatory & comes at an extra charge. Inquire here about our other yachts in our fleet

A dining area is set with a wooden table surrounded by white chairs. The table is adorned with light blue dishware and a white decorative centerpiece. A vibrant mural featuring tropical plants and ocean themes spans the wall, enhancing the space's relaxed atmosphere.

4.92 out of 5 average rating, 65 reviews

The Hideaway~Pool~Pickleball~Putt-Putt~Kayaks!

Welcome to The Keys Hideaway! 🌴🍍 The ✨ONLY✨ house in Marathon with its own private Pickleball Court and 4-Hole Putt-Putt Course!! Live your dream getaway in this Gorgeous 3BR Paradise in the heart of the Florida Keys. Sip a cold drink by your private pool 🍹, play Pickleball🎾, enjoy Putt-Putt ⛳, paddle out on a Kayak 🌅, or play Ping-Pong 🏓, end the day with a family cookout🔥. At The Hideaway, you’ll have it all, adventure, relaxation, and unforgettable memories!✨

4.97 out of 5 average rating, 122 reviews

A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.

Cottage in Islamorada

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

A tranquil pool is surrounded by lush palm trees, offering a serene atmosphere. The water reflects sunlight, while seating options are provided by the poolside. The design features a curved edge and a spa section, creating an inviting outdoor retreat.

5 out of 5 average rating, 8 reviews

The Roseate House at Grassy Key

Make The Roseate House at Grassy Key your next get away. Relax, fish, swim and explore at your own personal resort. The home is perfect for couples, family or girls retreat. Families return year after year to create their memories. Honeymooners appreciate the privacy as well as the attention to detail. Come live among the treetops in this vintage conch Key West style cottage situated half way between Key Largo and Key West.

4.9 out of 5 average rating, 117 reviews

A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.

Home in Cudjoe Key

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Popular amenities for Key West Holiday Accommodation with Fire Pit

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fire pit

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5 out of 5 average rating, 52 reviews

Marathon Keys Getaway • Pool • Hot Tub • NearBeach

5 out of 5 average rating, 18 reviews

Waterfront 2-bedroom Home w/Pool and Spa

A private dock is seen along a deep water canal, with a boat and jet ski moored nearby. Lush palm trees frame the waterfront space, while a two-story residence with a balcony stands in the background under a clear blue sky.

4.97 out of 5 average rating, 39 reviews

Waterfront home with direct Atlantic Ocean access

An open-concept living area is featured with light wood flooring and large windows allowing natural light. A modern dining table is set for four, while a cozy seating area includes a sofa and decorative wall art. Nautical elements enhance the coastal ambiance.

5 out of 5 average rating, 14 reviews

Marathon Paradise

The modern living area features a stylish glass-top coffee table made from natural wood pieces, surrounded by four bar stools at a sleek kitchen island. Soft lighting from the blue LED lights adds a subtle glow, while a fan and entertainment center contribute to the functional space.

4.9 out of 5 average rating, 78 reviews

Dream Vacation KCB Marathon with private pool !

A private pool with crystal-clear water reflects sunlight, featuring a large inflatable flamingo floating serenely. The surrounding area is bright and spacious, with a view of a light-colored house and tropical greenery in the background.

4.98 out of 5 average rating, 65 reviews

Casa Blue Flamingo

A sandy area by the waterfront features a stone fire pit surrounded by colorful Adirondack chairs. The calm Gulf of Mexico waters reflect a clear blue sky, with lush greenery visible in the background and a wooden dock extending into the water.

4.93 out of 5 average rating, 30 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

4.9 out of 5 average rating, 42 reviews

A private pool glistens under the sun, surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. In the background, a tiki palapa with a thatched roof offers shaded seating, complemented by lush tropical foliage and a distant pink house.

Home in Summerland Key

Pelico Palms Sunset Suites

Apartment rentals with a fire pit

Apartment in Key West

New place to stay

Fantasy Fest Huge 2 Story Townhouse Oldtown

Apartment in Key West

New place to stay

Key West Classic Gem

Apartment in Big Pine Key

An aerial view captures the expansive ocean and its varying shades of blue, framed by a sandy shoreline and a marina. A large pool is visible amid well-maintained grounds, alongside a collection of white-roofed condos, palm trees, and recreational areas.

Apartment in Marathon

Ocean Isles Yellowtail Row

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.

Sir David Waterfront

5 out of 5 average rating, 21 reviews

A scenic outdoor area features a thatched-roof gazebo overlooking the ocean. Palm trees sway gently in the breeze, and a paved pathway leads to the waterfront. The blue waters reflect the sky, creating a tranquil coastal atmosphere.

Apartment in Marathon

#1 Island Hideaway 89 - OCEAN FRONT

The exterior of a charming beachfront resort showcases three stories of pastel-colored buildings, framed by palm trees. A private marina with docks is visible in the foreground, while clear skies and vibrant greenery enhance the tropical setting.

Apartment in Key West

Waterfront Sunset Harbor Club Resort+Amenites. 1BR

4.87 out of 5 average rating, 55 reviews

A waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.

Apartment in Marathon

Little Venice in Marathon (in the Beautiful Keys)

The heated pool is surrounded by palm trees, offering a refreshing view of the ocean beyond. Lounge chairs are placed along the pool deck, which is paved with light-colored stones. Stairways lead to the building's upper levels, providing access to additional outdoor areas.

Apartment in Layton

4.71 out of 5 average rating, 7 reviews

Lovely Oceanfront Townhouse with pool & boat slip.

Cabin rentals with a fire pit

A bright living area features a comfortable sofa, a wooden entertainment unit with a TV, and a dining table with white chairs. Natural light enters through two windows, illuminating the space, which is decorated with framed photos on the walls.

4.61 out of 5 average rating, 89 reviews

2 Bedroom Pink Cabin Half/Duplex # 11

4.64 out of 5 average rating, 25 reviews

An outdoor area features a large chessboard with oversized pieces set up on a sandy surface. Colorful lounge chairs and palm trees are visible in the background, alongside a glimpse of the ocean. Additional games can be seen in the vicinity, enhancing the recreational space.

Private room in Marathon

Viamarhe Cabin-Private beach, Kayak, yard games

A welcoming living space features a cozy blue sofa with striped cushions and a dining area. Light-colored tiled flooring extends throughout the area, complemented by the refreshing green walls. Wooden cabinetry in the kitchen area provides ample storage, and a ceiling fan enhances airflow.

4.57 out of 5 average rating, 28 reviews

1 Bedroom Cabin Half/Duplex Unit B up on Stilts

A vibrant pink cabin is surrounded by tropical greenery and swaying palm trees. A white roof contrasts with the bright exterior, while a gravel pathway leads to the entrance. The landscape includes natural elements, creating a relaxed coastal environment.

4.29 out of 5 average rating, 14 reviews

2 Bedroom Pink Cabin Half/Duplex # 10

A bright yellow cabin is framed by lush greenery and shrubs. Large windows allow natural light to fill the interior, creating an airy feel. The surrounding landscape features a sandy area, adding to the cabin's appeal within the marina setting.

4.69 out of 5 average rating, 103 reviews

2 Bedroom Yellow Cabin

A bright kitchen area features teal cabinetry and a white refrigerator, complemented by a ceiling fan and a wall-mounted TV. A cozy blue sofa and a dining table with chairs are positioned nearby, with large windows allowing natural light to fill the space.