Vacation rentals with a fire pit in Stock Island

The sailing catamaran Purpus is shown gliding over the water, featuring a sleek white hull and a large deck. A spacious area is visible at the bow with crew members actively adjusting the sail. The overall design emphasizes both function and elegance.

4.9 out of 5 average rating, 30 reviews

Amazing 4 Bdrm, 4 Bath Catamaran- Sleeps up to 8

Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom, a full kitchen with everything needed for on board meal prep, spacious living areas down below and above on the decks. The boat is in great condition and has been well maintained inside and out. Purpus is docked in a first class marina with access to free parking, restaurants, bars, ship store, pools, ice cream shop and laundry. Charter options available for additional fee.

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.

5 out of 5 average rating, 13 reviews

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.

A colorful array of lounge chairs in yellow, green, and blue is positioned by a shared pool area. A thatched-roof cabana is visible, providing shaded seating near the water's edge. The lush surroundings and bright blue sky complement the inviting atmosphere.

4.89 out of 5 average rating, 19 reviews

Oceanside home 109, dock,kayaks,bikes,pool,fishing

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

A light blue oceanfront home is set against a backdrop of palm trees and tropical landscaping. The building features a screened porch and a roof deck, offering expansive views. A sandy beach area leads to calm waters with a floating dock visible nearby.

4.75 out of 5 average rating, 4 reviews

Tropical Paradise

Oceanfront home with private pool, boat dock, kayaks, and private beach Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24' boat allowed) screened in porch for dining There are 2 king bedrooms, 3rd bedroom has a queen with trundle 2 1/2 bath. This home has an open floor plan and recently remodeled kitchen.

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

You'll have a great time at this comfortable place to stay. 1 Bedroom Cabin located at the Old Wooden Bridge Resort and Marina in Big Pine Key, FL. 1/2 of a Duplex, up on stilts. It has a shared deck with a beautiful view over the marina. Guests can utilize amenities offered at Old Wooden Bridge Resort and Marina. There is NO Swimming in the Marina Boat Basin. This is a marina with houseboats and rental boats in the slips. There is a pet fee of $15 plus tax per night, per pet.

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.

4.87 out of 5 average rating, 115 reviews

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!

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.

4.9 out of 5 average rating, 10 reviews

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

The houseboat features a modern design with a spacious upper deck, complete with a shaded area for relaxation. The exterior showcases sleek lines and a multi-toned color scheme, while nearby marina amenities are visible in the background, contributing to the vibrant atmosphere.

Key West Oasis:Charming Retreat

Escape to our charming Key West houseboat, a serene oasis docked in a vibrant marina. This cozy retreat sleeps 4, featuring a comfy queen bed, a pull-out sofa, and a modern bathroom. Enjoy a fully equipped kitchen, Wi-Fi, and AC. Sway gently on the water, soak in stunning sunsets, or explore nearby Duval Street, just a short trip away. Perfect for couples or small families seeking a unique island adventure. Relax on the deck in paradise. Your Key West dream awaits!

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.

4.91 out of 5 average rating, 116 reviews

*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.

Tiny home in Summerland Key

A well-lit sleeping area features a spacious bed with decorative pillows and a cozy throw. Light wood accents and modern furnishings complement the room. A kitchenette area includes a mini fridge and Keurig coffee maker, with curtains providing separation and natural light from the windows.

4.86 out of 5 average rating, 14 reviews

Bungalow

Pet-friendly glamping in The Keys. Camp in comfort on your next Key West escape in an air-conditioned bungalow. Close to our amenities. Featuring a living room (with sleeper sofa), bathroom with shower, and a king-size bed, this vacation rental getaway sleeps 4. Our bungalows also boast patio table seating for four, Smart streaming TV, Wi-Fi, microwave, mini fridge, Keurig coffee maker, blow dryers, charcoal grill, and steamers.

4.9 out of 5 average rating, 62 reviews

The main saloon features wooden paneling, providing a warm atmosphere. Two leather couches flank a central table, while decorative pillows add comfort. A flat-screen TV is mounted above the seating area. A basket of towels sits on the table, with a soft rug running along the floor.

Houseboat in Key West

The simple life on Seaplicity!

Come stay on our beautiful & Super Comfy 38 ft Hunter Sailboat at the Perry Hotel & Marina! Start your morning with a fresh cup of coffee on board & "SIMPLIFY" your vacation with unrestricted access to all resort amenities! Two heated salt water pools, gym, laundry, and bathrooms and try one of the great restaurants onsite. Shuttle service takes you to old town Key West, leaving every hour from the hotel lobby.

An inviting cabin interior showcases warm wooden finishes and natural light. A small dining table is positioned near a couch and lounge area. A compact kitchen area features essential appliances and utensils, while steps lead to the outside deck, enhancing the boat living experience.

4.6 out of 5 average rating, 5 reviews

Anchored Escape: Sailboat Oasis!

Stay aboard a classic 35' Catalina sailboat in a peaceful marina. Enjoy cozy cabin accommodations with waterfront views, just steps from marina amenities including pools, restaurants, showers, and lounge. A unique Airbnb experience perfect for couples or solo travelers looking to relax, unwind, and soak up the coastal vibe. Minutes from local dining, beaches, and shops. Ideal for a memorable stay on the water!

Popular amenities for Stock Island fire pit rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a fire pit

4.86 out of 5 average rating, 7 reviews

A serene scene is captured featuring a sparkling blue pool surrounded by white lounge chairs. A tall palm tree sways gently in the background, with clear water visible beyond the pool, creating a relaxing atmosphere by the water’s edge.

Home in Key West

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Home in Marathon

Ocean Breeze Oceanfront

Home in Ramrod Key

Paradise in the Lower Keys

5 out of 5 average rating, 5 reviews

A community pool area is surrounded by tropical landscaping. Lounge chairs are positioned around the pool, with a large striped umbrella providing shade. Pool steps lead into the water, and a textured stone surface allows for easy movement. The atmosphere is relaxed and inviting.

Home in Marathon

Stunning* New* Home Pool in Ocean Breeze Marathon

Home in Key West

New place to stay

Gem of Key West

A spacious outdoor area features a well-maintained pool surrounded by a wooden deck and seating. A set of stairs leads to the upper level of the property. Lounge chairs are positioned near the water, with a patio umbrella providing shade.

Home in Big Pine Key

4.92 out of 5 average rating, 13 reviews

Turtle Cove

A person stands on a balcony, with views of nearby tropical palm trees and colorful homes. Sunlight filters through the space, providing a bright and open feel. The balcony features a wooden deck, with a railing that offers a glimpse of the surrounding area.

Home in Marathon

Number 44 Ocean Breeze

An open-concept living space is highlighted by a large kitchen island with a marble finish. A cozy seating area is visible, featuring a green sofa and various decorative elements. Artwork and a large wall-mounted TV add character to the room, which benefits from ample natural light.

Home in Key West

4.45 out of 5 average rating, 42 reviews

3-Bed Oasis in Midtown Key West

Apartment rentals with a fire pit

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.

Waterfront Sunset Harbor Club Resort+Amenites. 1BR

Apartment in Marathon

New place to stay

Marathon 2BR Villa on Lovely Waterfront Resort

Apartment in Big Pine Key

New place to stay

Key West Classic Gem

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

Apartment in Big Pine Key

A bedroom features two full-size beds, both adorned with colorful quilts in blue and green patterns. A wooden dresser with a lamp is positioned between the beds, and natural light enters through a nearby window, illuminating the space.

4.38 out of 5 average rating, 102 reviews

1 Bedroom Cabin Half/Duplex Unit A up on Stilts

Kayaks in vibrant green are positioned on a sandy beach, with paddleboards nearby. A dock extends over still water, bordered by pilings and a shaded umbrella, creating an inviting space for water activities.

Beach House Resort+Amenites, 2BR

A serene sunset scene is captured through palm trees, featuring the sun setting over the water. Silhouettes of sailboats can be seen in the distance, creating a calming visual along the horizon. The warm colors of the sky blend with the tranquil landscape.

Best Location in Key West

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

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.