Holiday rentals with a fire pit in Islamorada

Houseboat in Islamorada Tavernier

4.89 out of 5 average rating, 247 reviews

Florida Keys Dockside Paradise, Luxury Houseboat

Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers a unique blend of comfort, adventure, and waterfront living. Wake up to breathtaking sunrises, sip your morning coffee with all the marine life, and fall asleep to the gentle movement of the boat. Whether your celebrating something special or simply want a one of a kind getaway-it's the perfect home base for Keys adventures or peaceful retreats. An amazing experience Free park

A bright living area features a light wood floor and various seating options, including a wicker chair and a sofa adorned with colorful cushions. A coffee table is placed at the center, complemented by decorative wall art and a potted plant nearby.

4.94 out of 5 average rating, 109 reviews

Sugar Cane - Florida Keys tropical retreat

We have just completely renovated this condo at Ocean Pointe Resort and it's Insta-worthy. Every detail has been designed and considered. Sugar Cane is conveniently located near the best of the Florida Keys - close to Islamorada and Key Largo. The property boasts a large outdoor pool with a pool bar, hot tub, oceanfront beach and boardwalk, boat ramp, marina, tennis courts and children's play area. We manage Sugar Cane ourselves and live nearby so we have local knowledge and are very responsive

4.87 out of 5 average rating, 153 reviews

A serene sunset view showcases a circle of white Adirondack chairs positioned around a fire pit. The calm waters reflect vibrant hues of orange and purple from the sky, creating a peaceful atmosphere.

Townhouse in Key Largo

Sunrise Escape - Ocean Front Villa - Sleeps 10

Enjoy the sunrise while sitting on one of two terraces and sipping your morning coffee in the exclusive part of Kawama Yacht Club overlooking the Marina and Ocean. Enjoy the many choices for the day: Kayaking/paddle boarding just 20 steps from your door, walking to the south beach just 100 yards away, or walking to the beach jetty just across the marina. Or take a swim/snorkel in our swimmable lagoon or one of our two pools. Then bring a glass of wine to watch the breathtaking sunsets from our o

An open-concept living area features a comfortable sofa and loveseat, designed for relaxation. A stylish dining table accommodates four. A wall-mounted TV and electric fireplace add modern touches, while large sliding glass doors offer natural light and views of the surrounding landscape.

4.94 out of 5 average rating, 157 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

A private beach area is revealed, featuring rows of blue lounge chairs set on soft, sandy ground. Lush greenery borders the beach, while a wooden pier extends into the calm, turquoise water. A thatched gazebo provides shade, and scattered palm trees complete the coastal scene.

4.94 out of 5 average rating, 112 reviews

Your Happy Place - Oceanfront

Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside. Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay.

4.89 out of 5 average rating, 170 reviews

Apartment in Key Largo

Tropical Getaway

This light, airy two bedroom condo is located in the community of Kawama. Overlooks a small lake, where people swim, kayak and paddleboard. The condo community features two pools, tennis courts, playground, fishing, beach and marina. A long jetty extends out in the ocean where you can watch the beautiful sunrises or sunsets in the afternoons. Centrally located in Key Largo near restaurants, shopping and attractions. Come down and enjoy the peaceful atmosphere of our tropical area.

An aerial view of a blue, two-story house surrounded by greenery. The backyard features a swimming pool, red umbrellas, and seating areas. A patio leads to the pool, and the front yard is landscaped with grass. The neighborhood shows a quiet street with nearby houses.

4.98 out of 5 average rating, 120 reviews

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.

✨Bring the whole family to this great located house with a nice pool with spa, combo game table and lots of room for fun, and enjoy the beach, restaurants and entertainments around the area. ✨5BRs with smart TVs and comfortable mattresses and pillows. 3BR upstairs/2BR downstairs. ✨3 bathrooms, 1BR downstairs/2BR upstairs. ✨2 kitchens fully equipped with everything you may need. ✨Nice and quite neighborhood. ✨Sunsets are amazing at The Florida Keys. ✨Guest are always our priority.

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.

4.9 out of 5 average rating, 109 reviews

NEW! CASA PALMA - Golf Cart, 2 Kings, Pool, Kayaks

Welcome to your Key Largo vacation rental. This oceanside villa is family friendly and filled with amenities, including a private golf cart, one adult kayak and three kids kayaks, pickleball and tennis courts, multiple pools, and a unique swimming lagoon. Spend your days kayaking, fishing, boating, snorkeling, or visit the nearby beach at John Pennekamp State Park. Our villa has earned hundreds of 5-star reviews and Superhost status on all major platforms. No Hidden Fees!

A bright living space features a comfortable gray sofa and a recliner, complemented by a white coffee table adorned with decorative items. The dining area, with a white table and several chairs, extends into the modern kitchen equipped with stainless steel appliances and a breakfast bar with stools.

4.88 out of 5 average rating, 162 reviews

Reel Large END Unit in Ocean Point Suites

Sept - Nov. building improvements will take place and our rates have been heavily discounted for the inconvenience. No work will take place during the Weekends or Holiday's. The amenities are not affected. Paradise awaits you in this large END unit, 2 BR/2BA in the highly desirable community of Ocean Pointe Suites! Newly renovated Modern Beach decor unit with breathtaking views from our Private beach and Marina are just a few highlights of this island retreat.

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!

4.94 out of 5 average rating, 110 reviews

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

Popular amenities for rentals with a firepit in Islamorada

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a firepit

A serene view is presented from the pool area, featuring gentle waves lapping at the shore and numerous sailboats anchored in the harbor. Two palm trees provide shade, and a well-maintained lawn borders the pool, enhancing the coastal ambiance.

5 out of 5 average rating, 10 reviews

Sandbox

4.98 out of 5 average rating, 50 reviews

Grouper Getaway @ Ocean Isles Fishing Village

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, 53 reviews

Marathon Keys Getaway • Pool • Hot Tub • NearBeach

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, 9 reviews

The Roseate House at Grassy Key

Aerial view of a waterfront community featuring multiple homes surrounded by lush greenery. Two circular pools are visible in the foreground, with docks extending into the water. A sailboat is seen on the horizon, showcasing the serene setting.

4.95 out of 5 average rating, 104 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

An aerial view captures a winding pool surrounded by lush palm trees and beach loungers. The pool's turquoise waters reflect the surrounding greenery and the bright sun. White buildings with large windows are visible in the background, enhancing the inviting atmosphere.

5 out of 5 average rating, 13 reviews

New! 4-Story Villa w/ Rooftop & 3 Private Suites

The outdoor area features a sandy patio surrounded by palm trees, with several blue Adirondack chairs facing a shaded seating area under a white gazebo. The spacious home stands in the background, showcasing multiple balconies and a light-colored exterior.

4.89 out of 5 average rating, 74 reviews

Gorgeous Ocean View Home!

5 out of 5 average rating, 10 reviews

Remodeled July 2025 2/2 Townhouse

Apartment rentals with a firepit

5 out of 5 average rating, 17 reviews

A bright living area features a light-colored sofa adorned with decorative pillows, complemented by a glass coffee table. Large windows invite natural light, revealing views of the lush landscape outside. A mounted television and coastal artwork complete the serene environment.

Flat in Tavernier

Unbeatable Views from Lux Oceanfront Suite

5 out of 5 average rating, 7 reviews

A bright living area features large windows, allowing natural light to fill the space. Soft blue walls complement the light-colored furnishings, including a spacious curved sofa and a distinctive wooden coffee table. A ceiling fan circulates air, while a decorative plant adds a touch of greenery.

Flat in Tavernier

New Coastal Escape 2BR/2BA Oceanfront Condo

A view of the marina is captured, showcasing several boats docked along wooden piers. The scene features sandy beach areas with colorful chairs and kayaks scattered along the shoreline, framed by palm trees and under a clear blue sky with scattered clouds.

5 out of 5 average rating, 13 reviews

Waterfront Condo on Blackwater Sound + 25’ Slip

A spacious living area features large windows that offer views of the marina and ocean. Comfortable seating arrangements include two leather sofas and a stylish coffee table. Natural light brightens the space, while wood paneling adds a modern touch to the decor.

4.88 out of 5 average rating, 33 reviews

Overlooking Marina/Ocean view & FREE GOLF CART

The room features tile flooring and a spacious bed with nautical-themed bedding, complemented by a nightstand. A private entrance is visible, along with an air conditioning unit mounted on the wall. Natural light enters through a nearby window, enhancing the comfortable ambiance.

4.67 out of 5 average rating, 245 reviews

Motel Room #1, Private Entrance, Beach and Marina

4.94 out of 5 average rating, 34 reviews

A relaxing outdoor area features a sparkling pool surrounded by lounge chairs and vibrant blankets draped over the edge. Lush greenery and palm trees provide natural shade, creating an inviting space for leisure and family gatherings.

Flat in Islamorada

La Casa HMH

A sandy beachfront area is presented, featuring several white Adirondack chairs arranged around a small table. Soft clouds drift overhead, and the ocean extends into the horizon. Decorative string lights are visible above, enhancing the outdoor setting.

5 out of 5 average rating, 8 reviews

Kawama New Listing!

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.

Flat in Marathon

#1 Island Hideaway 89 - OCEAN FRONT

Cabin rentals with a firepit

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, 90 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.

4.59 out of 5 average rating, 29 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.