91 properties available

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 Big Pine Key, Florida, United States. Slice of Paradise: Captivating Open Water Views, Deep Canal, Dockage, Heated Pool, and Pet-Friendly! Escape to 'Slice of Paradise' – a tropical waterfront haven nestled on the picturesque Big Pine Key. This stunning retreat showcases awe-inspiring open water views and provides a generous 60 feet of canal seawall, ensuring a perfect docking spot for your boat. With swift access to both the Atlantic and Gulf waters, you're perfectly positioned to relish the exceptional fishing and diving adventures that the Lower Keys are celebrated for. Gather your nearest and dearest to savor the good life – whether it's sipping your favorite cocktail on the screened porch while watching boats sail by, or watching the kids revel in poolside fun. 'Slice of Paradise' promises a world of relaxation and enjoyment. While this slice of heaven offers endless entertainment, should you yearn to explore the Keys, Key West is just a 40-minute drive away, and Marathon is a mere 25 minutes by car. Unlock the door t

Located in Big Pine Key, Florida, United States. Boater's Paradise with Boat Dock / Quick Open Water Access Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with a boat dock. Steps away from ocean water. Located in one of the best fishing spots in the Florida keys. Large canal with quick Gulf & Ocean access to explore the Florida Keys by sea. Newly remodeled and nicely appointed 2 bedroom / 2 bath canalfront home. Everything you need for your time in paradise! There is a king size bed in the master and queen size bed in the 2nd bedroom.Good-sized closets. Flat screen TV in the living room and both bedrooms.Gas grill and outside table downstairs.Concrete dock.Set on a canal right off Bogie Channel, the water access doesn't get any better than this.

Located in Big Pine Key, Florida, United States. See the ocean from every room. September rate only 2,520.00. Stay 1 week or 4! You have found it. So quiet. So beautiful. On Bogie Channel. One mile from No Name Pub. Only 30 miles from Key West! FUN IS EVERYWHERE. With ocean views from EVERY room in the home, this unique property boasts two completely separate units with an amazing one-bedroom, one-bath, and full kitchen, living, and dining area upstairs and a two-bedroom unit with a full bath, kitchen, living room, and dining area downstairs. There is plenty of outdoor space on your private oceanfront beach with a HOT TUB. This rental is perfect for two couples, two families, or multigenerational families. The neighborhood is quiet and the property is located on a dead-end street located on Doctor’s Arm on Big Pine Key. If you are looking for the perfect, quiet, oasis in the Florida Keys, this is your vacation home! With sunrise views over the open ocean and sunset views looking out over the canal with your private boat ramp, you ca

Located in Big Pine Key, Florida, United States. Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut with ice maker, 50" TV, refridgerator, fire pit area, and beach with floating dock for your boat! We also have kayaks, SUP's, and bikes for your outdoor fun. You will not want to go inside, but when you do, you will find a very "Keysey" living space with plenty of water views and gallery of underwater pics you can purchase and take home with you. Only 9 miles from Bahia Honda State Park one of top 25 beaches in the US. We are also famous for key deer only found on Big Pine Key. They are friendly and everywhere. You can also walk to No Name Pub a famous eatery.

Located in Big Pine Key, Florida, United States. Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel, Pool & Dockage! Introducing Castaway On The Keys, your luxurious open water sanctuary awaits! Nestled in the esteemed Doctor's Arm subdivision of Big Pine Key, near the renowned No Name Pub, this exceptional retreat offers a blend of opulence and natural beauty. Start your days with awe-inspiring open water views of Bogie Channel from your deck, savoring the tranquility over morning coffee or afternoon cocktails. While you soak up the sun, family and friends can cool off in the inviting pool. Embark on aquatic adventures by boat, as you turn left for the renowned backcountry fishing or serene sandbars, or turn right for exciting Atlantic escapades, including reef and deep-sea fishing. Beyond the indulgent offerings of the house, and the allure of Big Pine Key, the vibrant allure of Key West is merely 45 minutes away, while the captivating charm of Marathon beckons within 25 minutes. Unveil the epitome of F

Located in Big Pine Key, Florida, United States. Tarpon Time | Spacious 4 bed/3.5 bath retreat with pool & boating on Big Pine Key Escape to paradise at Tarpon Time, a stunning brand-new monthly rental nestled in the heart of the Florida Keys. This 4-bedroom, 3 1/2-bath home offers an idyllic retreat with breathtaking views of Bogie Channel and No Name Key. With 2,500 square feet under air, this spacious haven provides ample room for the entire family.The house shares a 90-foot dock right on the channel with two other properties, so total boat length is limited to 28 feet.The expansive living area boasts comfortable seating and a Smart TV, creating the perfect space for relaxation and entertainment. The well-appointed kitchen, complete with a pantry and bar seating for 4, offers scenic views of the bridge to No Name Key. The adjacent dining area accommodates 8 guests.The bedroom layout is thoughtfully crafted for comfort and privacy. The primary suite features a King bed, large flat-screen TV, a spacious shower, double vanities and a

Located in Big Pine Key, Florida, United States. Peaceful island home on canal with quick access to Bogie Channel. Peaceful island home located in Big Pine Key's wonderful Doctor's Arm neighborhood. Perfect for chance to relax, fish, and commune with nature.This Fisherman's paradise is located right off Bogie Channel and has a covered fishing station, bait freezer, and enclosed outdoor shower. Enjoy the evenings grilling on the upper deck or walking to the famous No Name Pub.

Located in Big Pine Key, Florida, United States. Fishing, swimming and relaxing on the porch in Big Pine Key Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Keys. Its located in Tropical Estates, a quiet upper scale community with water access throughout. A perfect location if you are looking for a tranquil island setting but close to the fun as Key West is just 25 miles south. This home has 3 large bedrooms, 2 with 1 queen bed, 2 double beds. 2 with adjoining full baths!, The baths are roomy, one with a walk in shower and the other has a tub if you feel like relaxing. Both have views of palm trees and the sunset! The master bedroom has access to the screened in porch and the views of Palms thru the windows give it a perfect tropical feel. The screened in porch runs the length of the house over looking the canal. With plentiful seating for relaxing and tables for outside dining. Manatees, sharks and barracudas can be seen on occasion as well as parrot fish, snapper and colorful coral. The living room ha

Located in Big Pine Key, Florida, United States. POOL! STUNNING NEW OCEANFRONT 4 Bedroom 3+ Acre Private Estate Absolutely stunning, OCEANFRONT, dream home with panoramic views like none other. Truly one-of-a-kind property. BRAND NEW POOL just completed.This brand new, beautiful 4 bedroom, 3.5 bath OCEANFRONT home is situated on a 3+ acre private peninsula in Big Pine Key offering 2,500+ square feet of spacious, new living space, plus an additional 800 sqft of covered oceanfront decks/porches/balconies. Our dream kitchen features an 8-seat, 9’ x 5’ quartz island with ocean views abounding. Our great room includes (2) 8’ sliders that pour open to covered deck space featuring one-of-a-kind panoramic ocean views. Gaze at the water from every room in the house. (2) Master bedrooms offer ample space for you and your family. The upstairs master features a private balcony and a luxury soaker tub. Two additional bedrooms feature queen beds, ocean views and large windows.Enjoy over 3 acres of private, professionally landscaped oceanfront prop

Located in Big Pine Key, Florida, United States. Private water front property with ocean access Beautiful 15,000 sq ft water front property. Steps away from the famous No Name Pub. Steps away from the no name bridge which is great for fishing. Also in walking distance from boat rentals and kayak rentals although we have kayaks to use at our place during your stay. 30 minutes from key west and 10 minutes to the beautiful beaches and Bahia Honda state park. Also have over 30 ft of docking for your boat needs. Great Location over all ! You will fall in love with our rental.

Located in Big Pine Key, Florida, United States. Waterfront home with screened lanai, patio, central AC, & washer/dryer The Nautical NimbusOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Let your worries drift away as you drift into a seaside reverie at this peaceful Big Pine Key retreat. Sure to be a favorite for anglers and idlers alike, this private home comes primed for classic Conch living, with highlights including waterfront views of Pine Channel and an ideal location close to dive shops, snorkel tours, and fishing charters. Big Pine is home to the 9,200-acre National Key Deer Refuge, and on the north end of the key, you can find some great opportunities for wildlife sightings at Blue Hole or the Fred C. Manillo Trail. After your hike, quench your thirst with a cold drink at the world-famous No Name Pub. Key West is less than 30 miles from your front door. The home also makes an ideal basecamp for Lobster Season.At home, relax on the screen

Located in Big Pine Key, Florida, United States. Tiny House, 30 min from Key West, free parking and pool Adorable cottage, with close proximity to everything. Just 35 min from Key West, nested in the famouse Deer key, Big Pine key, very quite RV community. The house features 500 SQ ft of space (50 SQ meters), amazing backyard. It accommodates up to 4 guests! patio are has rattan chairs and sofa with coffee table and grill.

Located in Big Pine Key, Florida, United States. Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friendly Accommodations! Discover the epitome of Keys living at "Rising Sun," a captivating waterfront home nestled on the serene shores of Big Pine Key. This charming abode offers an authentic experience of the vibrant Keys Life, immersing you in the essence of island living. With a private boat dock along the seawall, you can effortlessly moor your vessel and embark on a swift journey down the inviting canal to Pine Channel. Whether you choose to navigate left to the expansive Atlantic or turn right to explore the tranquil backcountry, the possibilities are boundless. Indulge in moments of tranquility on the inviting porches and patios that grace the property. Start your day with the gentle embrace of a morning coffee or unwind with your favorite cocktail in hand, all while watching the gentle parade of boats meander by. This unique round home offers a plethora of activities to engage in, ensuring you're never

Located in Big Pine Key, Florida, United States. 300’ Private Beach, Pool & Rooftop w Panoramic Ocean Views Looking for the perfect estate to host an exclusive beach wedding? The Minty Mermaid is undoubtedly the most unique, serene, and picture-perfect property you will ever come across. Located in an environmentally protected sanctuary, this 4 bedroom 4 bath authentic Keys Villa is unlike any other home you will ever see. Watch baby sea turtles hatch on the beach in your backyard during late summer, or catch a glimpse of the world famous Key Deer roaming throughout the salt ponds. Did you know Big Pine Key is the only place in the world these tiny deer are found?If you’re looking for an “off the grid” home with enough amenities to make you want to stay forever, you’ve come to the right place. Pour yourself a drink at the poolside tiki hut, while you indulge in the salty island breeze blowing through your hair. At sunset, take a long walk on your very own private beach or paddle board by the mangroves, along the shoreline, while bird

Located in Big Pine Key, Florida, United States. Upscale ocean front home & easy canal boat access to Gulf or Atlantic THE ADVENTURER'S RETREAT - BIG PINE KEY BUNGALOW IS YOUR HOME AWAY FROM HOME WHERE YOU CAN RELAX AND ENJOY THE CENTRALIZED LOCATION TO ALL THE BEST ADVENTURES THE FLORIDA KEYS HAVE TO OFFER. ALL ROOMS HAVE AN OCEAN AND/OR CANAL VIEW!-Location- The Big Pine Key Bungalow is located on the East side of Big Pine Key. The living room and kitchen area opens up to three large sliding glass door windows giving an expansive view of the Bogie Chanel and No Name Key. Within a 5 minute drive (or less), you get to nearly all the essential items on the island. The supermarket, WinnDixie, is a 5 minute drive and offers home deliveries of your groceries. You will also find many restaurants nearby as there are several in the same complex as the WinnDixie. Grabbing some drinks at the drive through liquor store, Coconuts, is always an interesting experience! Big Pine also has a Walgreens, CVS, ACE Hardware, UPS, and many fishing stores