72,107 properties available

Located in Big Pine Key, Florida, United States. Keys 3 Bedroom Corner Home near Beach & Key West Spacious very private home only 3 miles from beach and 25 miles from Key West. Home is only 1 mile from boat ramp and close to one of the USA's Best fishing spots and many sand bars to enjoy what the keys have to offer. House offers an open concept layout allowing guests to enjoy large family gatherings, and make new memories with your loved ones.

Located in Big Pine Key, Florida, United States. Newly Remodeled Corner House on the Water There’s no better place to experience the laid-back calm of the Florida Keys than this bright and newly-remodeled two-bedroom getaway! Step inside to find an open-concept layout boasting a new kitchen, new beautiful floors, and comfortable furniture. The remodel includes newly renovated bathrooms, a new AC unit, new kitchen appliances, new washer/dryer, and new TVs. The full kitchen is equipped with stainless steel appliances, ample counter space, and a prep peninsula to help you prepare a fantastic meal. You can enjoy your creations from the dining table while the kids chatter away from the breakfast bar stools or outside on the furnished deck as an al-fresco meal. Don’t forget to use the central AC to keep everything nice and cool while you post your best selfies to your social media via the free WiFi.Possible Activities:- Enjoy some salt water fishing downstairs while surrounded by local wildlife including Key Deer- Take in the Key West suns

Located in Big Pine Key, Florida, United States. Keys To The Kingdom! Private Oceanfront Retreat with Beach and Pool There's no better place to experience the magic of the Florida Keys than this bright and remodeled three-bedroom getaway! Step inside to find a spacious open-concept layout boasting an ocean view, beautiful floors and comfortable and attractive furniture. After spending an afternoon on the water, come home to kick back and relax in the large, heated swimming pool (39'x14') or watch a good movie on the TV. The full kitchen is equipped with stainless steel appliances, ample counter space, and a center prep island to help you prepare a fantastic meal and you can enjoy your creations from the furnished balcony for an alfresco meal. You'll love taking advantage of the home's private beach during your stay and the private washer/dryer will wash away all the salt when you're done. Don't forget to use the central air-conditioning to keep everything nice and cool while enjoying the free WiFi. Rest assured that the power will al

Located in Big Pine Key, Florida, United States. Newly renovated cozy and spacious beach house with breathtaking ocean front Spectacular ocean front home awaits you in Big Pine Key. Cozy family getaway with breathtaking ocean view and over 450 foot dock you will feel as floating on water. Enjoy this 2 bedroom/ 2 bath fully furnished and upgraded home to meet all your expectations and needs. Property also included a 1 bedroom/1 bath guest house with a full kitchen and living room.

Located in Big Pine Key, Florida, United States. Spacious 5 bedroom with quick boating access to both the Gulf & Atlantic Ocean Located in a prime area of Big Pine Key, this Gorgeous 5 bedroom house is only 400 ft from the open Ocean. Pine Channel is just outside the mouth of our canal making for super easy & convenient boating access to the Gulf or Atlantic Oceans. This concrete home is a one of a kind with cathedral ceilings over a large open living/kitchen area. Plenty of room for a big crowd & family. The Kitchen is a cooks dream with a large island and over 25 ft of Sile Stone counter tops and beautiful Kitchenmaid wooden cabinets. The master bedroom is large with a nice sitting area and 2 man bathtub in the room. Owned & built by a local conch, this house is full of cheerful vibrant colors and has that Key'sie atmosphere. It is a Google home which includes 6 speakers throughout the house and a LCD display in the Kitchen. Handmade driftwood furniture, life size Shark Sculptures and various art work by Artist Mark Rackley

Located in Big Pine Key, Florida, United States. New Listing! Beautiful Canal front , Key Deer and jacuzzi. -Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property.- Dock and fish cleaning station.-Excellent access to Atlantic and Gulf, minutes to the best lower keys fishing in country.-Nice Jacuzzi to enjoy the sunset.- 15 minutes from Bahia Honda State Park with a beautiful beach.-The Key where the deer live . -Tiki bar to relax watching the canal.-Full kitchen-TV in every room.-Directv and internet provider

Located in Big Pine Key, Florida, United States. Luxury and Lovely Water Front House If you're looking for a low-key vacation, Big Pine Key is the place for you. In Big Pine Key, about 100 miles south of Miami and 30 miles north of Key West, you'll find relaxing, water-borne activities such as boating, fishing, scuba diving and snorkeling. Fishing, of course, means seafood, and you'll find some of the nation’s best seafood restaurants in Big Pine Key and on nearby keys. Don't miss the beautiful white sand beaches at Bahia Honda State Park. At the National Key Deer Refuge, you can see the tiny and very cute wild deer known as Key deer, about the size of a large dog. The kids will love it, and so will you.

Located in Big Pine Key, Florida, United States. Awesome Open Water View at Blue Heron Estate 15 Acre Open Water Estate. Four bedrooms each with their own private bathroom. Large pool. Breathtaking views of the sunrise and historic Bahia Honda Bridge. Secluded location at the end of the road. Less than 2 miles to the Atlantic and around 3 miles to the Back Country. Check out the satellite view of the property and see for yourself. No doubt, it is one of the best boating locations in the Lower Keys. With a 100' long dock adjacent to the property. Affordable pricing. The Blue Heron Estate is perfect for your next family get together. Up to $1000 damage protection will be charged if damage and/or excessive cleaning is reported.

Located in Big Pine Key, Florida, United States. Big Pine Waterfront Getaway Welcome to our charming canal-front bungalow in the Florida Keys! This delightful rental offers an unforgettable experience for your coastal getaway. With 3 bedrooms and 2 bathrooms, our bungalow comfortably accommodates up to 8 guests, making it perfect for families or groups of friends.Please note that Monroe County requires a minimum rental period of 28 days for this property. Thus, all bookings must be compliant with this rule. We cannot agree to any rentals for less than 28 days.Nestled along the canal, this property provides easy access to the open water, just a quick 5-minute boat ride away. Whether you're an avid boater or simply looking to explore the mesmerizing seascape, you'll appreciate the convenience and adventure that awaits you. Enjoy the convenience of two docks and a fish cleaning station for guests to use.Prepare to be captivated by the stunning sunsets that grace our little slice of paradise most evenings. Witness the sky ablaze with hue

Located in Big Pine Key, Florida, United States. Florida Keys Water Front Vacation Home with Pool Beautiful 3-BR waterfront house with pool that is located directly on an ocean canal with easy access to the Gulf of Mexico or Atlantic Ocean. Private outside shower. 75-ft dock for boat. Home of the Key Deer and Blue Hole (the deer walk past house daily).After a day on the ocean, sit in backyard under the tiki hut with a cold drink and grill your fresh catch of the day! This house is a great place to host a group dinner or have a romantic evening. The house is located 25 miles north of Key West, and 20 miles south of Marathon. The house is located in a quiet neighborhood and it's the perfect place for a vacation getaway. It's also close to local restaurants, bars, grocery store and a miniature golf course. Available for month-long bookings in Spring 2024.

Located in Big Pine Key, Florida, United States. Mariner's Manor - Private Canal-Front Oasis on Big Pine Key 3/2 Discover your perfect getaway on Big Pine Key with this exceptional three-bedroom, two-bathroom canal-front home. Fully gated and offering complete privacy, this home provides direct access to the bay and is just a short boat ride to open water fishing. Experience world-class fishing, snorkeling, and diving from this prime location with Looe Key Coral Reef just around the corner and some of the Lower Florida Key's finest sandbars ready to receive you. The home's serene setting ensures a peaceful retreat, while the convenience of nearby aquatic adventures awaits. Relax in the comfort of this well-appointed vacation rental, and create unforgettable memories in the stunning Florida Keys. Book your stay today and enjoy the ultimate private oasis on Big Pine Key!This is a 28-night minimum rental per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 years of age or ol

Located in Big Pine Key, Florida, United States. Tarpon Tales | Pet-friendly home with fantastic boating access on Big Pine Key An angler's dream! Comfy 2 bedroom / 2 bathroom home on a large and lush canalfront property just minutes from the channel. Lots of relaxing outdoor living space. Fully fenced and very private. Close to the community park. Fully outfitted kitchen. Each bedroom has a king bed. Plenty of dockage. Excellent fishing retreat, just minutes from the channel.Well-behaved dogs (max 2) considered with manager's prior approval and $250/per dog nonrefundable fee.This home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 4 people, and all guests need to be registered with the property manager. No smoking. There's a cap on electric ($250) and water/sewer ($150).

Located in Big Pine Key, Florida, United States. Relaxing Florida Keys canal front home in nature preserve Welcome to Kokomo Palms!This relaxing getaway is a single family, canal front home located on Big Pine Key. It offers two bedrooms and one bathroom. Four guests maximum. Situated on a key deer nature preserve, you can watch the sunset view from your front porch every evening. With a large concrete dock it offers plenty of room for your boat. Quick access to back country or ocean side. There is a large, spacious yard with an updated, comfortable interior. You are located 10 minutes from the local grocery store, 20 minutes to Marathon and 40 minutes to Key West! Come embrace the Key’s lifestyle and all is has to offer!No pets or smoking allowed on property. No parties or large groups as this is a quiet neighborhood. Maximum sleeping capacity is 4. County zoning requires a minimum rental period of 28 nights. No exceptions!Bedroom #1- Master- King bed- Dresser- Two night stands with 2 lamps- 40 inch flatscreen Smart TV with access

Located in Big Pine Key, Florida, United States. 4/2 Fully Furnished Canal Home 4/2 furnished Seasonal Rental Gorgeous 4/2 stilt home on a canal. Master bath has a jetted, roman tub. Queen beds with linens in each bedroom. Vaulted wood ceilings in the living areas of the home. High end kitchen with stainless steel appliances and kitchen island. Back bedroom has full view of the canal and it's own private balcony area. Lots of deck space in the back yard and side area of the home. Outdoor shower is located on the back deck. Located on a quiet street that dead ends. Centrally located to local shopping, schools and grocery stores. Owner is a FL Licensed Real Estate Broker.Paradise found! Bring your bathing suit and the key is in the conch shell. This beautiful home is centrally located to shopping and activities. Approximately 15 minutes to Marathon, FL and 30 minutes to Key West. Come visit Blue Hole and see the nature Big Pine Key has to offer. View Key Deer in their habitat and visit Bahia Honda State Park that are only minutes a

Located in Big Pine Key, Florida, United States. Beautiful Family Big Pine Retreat! Short drive to Key West! Big Pine Key offers the most peace & tranquility of the FL Keys! This home offers plenty of space and parking along side with waterfront dockage space. A private jacuzzi and a wonderful open-layout home perfect for entertaining. You have plenty of space to enjoy an amazing time with your guest. Next time your thinking of disconnecting from city life consider booking our gorgeous Big Pine Retreat!

Located in Big Pine Key, Florida, United States. Beautiful Keys Getaway! Located on deep water canal for quick access to This is a 2 bedroom, 2 bathroom concrete block house. It is located on a clean swimming canal right off Pine Channel. This Big Pine Key home has an open floor plan with updated kitchen, dinning room and living/TV room. The master bedroom has a King size bed with its own en suite. The second bedroom has a Queen size bed and a twin bed. Each bedroom has a TV. The living room has a queen sofa sleeper for when guests visit. This home sleeps 6 comfortably. The lower keys is known for world class fishing, boating, snorkeling and diving. This house comes with a kayak for use for those who would like to take a leisure tour of the area as well as 2 cruiser bikes. The home has a 75' seawall with a step down dock and fish cleaning table. This home also has a 40' lap pool for cooling off after a day of fishing or just to lay around and catch some Rays. Dolphin Marina/Ramp is located minutes away on Little Torch K

Located in Big Pine Key, Florida, United States. New Beach House-Boat & Dog Friendly 30 mins Key West Brand new! Pet friendly, quiet and clean beach house. located on Big Pine Key. Only minutes from boat ramps and white sand turquoise beaches at Bahia Honda State Park. Plenty of tiki bars within close proximity, or if you like to cook, the new kitchen is equipped with all brand new utensils and an oversized stainless-steel fridge. The home offers all you need to relax in comfort with a cloud couch, TVs, outdoor balcony seating and fire pit under the covered terrace. Down the street is a brand-new state of the art waterfront park with tennis courts, skate park, bocce courts, shuffleboard, and playground. Just 30 mins to downtown Key West if your looking to check out the famous Duval St. If you are looking for a quiet, remote, clean, and relaxing home look no further!

Located in Cudjoe Key, Florida, United States. Cottage with swimming pool and dockage, just minutes to Key West! Cottage #3 - Quaint, clean, comfortable cottage just 20 miles from Key West. Located on the oceanfront. Cottage offers a full kitchen, screened patio, a single bedroom with a queen bed. This cottage is only steps away from our pool. The dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Cottages to be your Home Away From Home.

Located in Summerland Key, Florida, United States. HIDDEN HAMMOCK RESORT Palm cottage The Palm Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently renovated. The kitchen, bathroom tile and furniture are new. ACCOMODATIONS:Each unit comes with TV, AC & WIFI. UNIT #1 has full kitchen and UNIT #2 has efficiency kitchen with refrigerator and microwave oven. Enjoy the communal outdoor pool and covered patio that has a gas grill and picnic area. ACTIVITIES: Fishing adventures, bird watching, water sports or some down time relaxing in nature and the beauty of the most desired key in Florida.We’re twenty-five miles to Key West for dinner and nightlife or walk down the block to the local tiki bar, Tonio’s.We have plenty of space for your boat and trailer. There is a boat ramp just down the block at Tonio's that can handle flat boats 21' or smaller and the boat ramps at Cudjoe Gardens Marina (477 Drost Ave.) and Little Torch Key (SR 4A & County Road) can handle larger boats for a minim

Located in Summerland Key, Florida, United States. Kelly's Kabin - Adorable Private Summerland Key Cottage Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors. There is ample parking for multiple vehicles and your boat. The property is fully licensed for nightly, weekly, or monthly rentals.Summerland Key is located at mile marker 24, which allows you to enjoy short drives north to Big Pine Key, Bahia Honda National Park, and Marathon Key. The major attractions of Key West are only 35 minutes to the south. Public transportation is conveniently accessible immediately adjacent to the cottage. No need to drive or find parking! Looe Key, with its phenomenal snorkeling and diving, is accessible through a variety of local charters. Kayaks, paddleboards and bicycles can be rented nearby. Fishing options include back country fishing, ocean fishing or bridge fishing. A lovely bike path is located at the back of the property. This property is close to favorite local r

Located in Summerland Key, Florida, United States. Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home, Dockage & Dog-Friendly Welcome to Key Blessing, your gateway to experiencing the quintessential Keys Life! This charming 3-bedroom canal front home, nestled on Ramrod Key, offers the perfect blend of relaxation and adventure. As you arrive, you'll appreciate the convenience of docking your boat along the sea wall, allowing you to indulge in fantastic fishing just moments from your doorstep. The sea and its bounty are at your fingertips, promising memorable angling experiences. Start your mornings on the screened porch, sipping your coffee or favorite cocktail as you watch boats lazily drift by. The serene atmosphere and gentle sea breeze create an ideal setting for unwinding and taking in the picturesque views. While there's plenty to keep you entertained right at this house, the Florida Keys beckon with their allure. If you're in the mood for exploration, you'll find a treasure trove of restaurants just minu

Located in Summerland Key, Florida, United States. Mad Mahi Canal with pool This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atlantic. Sea Wall has room for (1) 24' boat. This home can sleep 7 adults and 2 small children. There are 4 bedrooms and 4-1/2 bath. Fully stocked modern kitchen, great out door space and a separate apartment for privacy. Swimming pool recently installed and complete.There are 3 Kayaks and 4 bikes included as well as a ping pong table.Your property manager lives nearby and is available if you have any requests during your stayQuite Residential NeighborhoodYou will be provided with check in instructions prior to your arrivalThe perfect home for a family gathering. With a total of 6 sleeping areas, you can spread out and have a space for your own private time.This home is located on a canal with boat dockage and has a tropical pool for cooling offUber, Lyft and Taxis area available as well as Public Bus transportation. It is recommended that

Located in Summerland Key, Florida, United States. Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83) Pet-friendly glamping in The Keys. Camp in comfort on your next Key West escape in an air-conditioned bungalow. Featuring a living room (with a sleeper sofa), a bathroom with a 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, a microwave, a mini-fridge, and a Keurig coffee maker.Find paradise at Sun Outdoors Sugarloaf Key, located along a seven-acre saltwater lake and surrounded by state parks and mangroves. Our unique luxury resort embraces the essence of Key West living. Enjoy a cool beverage at the peninsula tiki bar. Stroll the lakefront boardwalk. Or cruise the lake on a paddleboard, paddleboat, or kayak. Outdoor pool too!Note: No smoking is permitted in the bungalows. Bed and bath linens are provided.Pets - allowedSmoking - not allowed

Located in Cudjoe Key, Florida, United States. Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West Cottage #14 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound with 2 swimming pools. Spacious cottage offers a full kitchen, screened patio, two queen bedrooms. The pool, dock and seawall are all available to our guests. A coin laundry is also available on site. Whether you come to the Florida Keys to escape the winters, or enjoy the calm waters and great fishing and diving of the summers, you will find Cudjoe Oceanside Cottage to be your Home Away From Home.