91 properties available

Located in Big Pine Key, Florida, United States. New listing 3bd/2bt Sleeps 8 "Sunset Paradise Villa" on canal Big Pine Key *BIMINI TOPS or Fold down T-tops boats ONLY DUE TO WATSON ST BRIDGE. Sunset Paradise Villa is a 3 Bedroom/2 Bath canal/water front tropical villa that sleeps 8+ located in beautiful Tropical Bay Estates on Big Pine Key in the Florida Keys. This remodeled and newly furnished villa with Sunset views from screen patio that is loaded with amenities including its own canal for your boat (Bimini Tops only due to Watson St bridge) fishing, swimming, kayaking and quick access to explore the Backcountry, Gulf and Atlantic Ocean. Outside you'll find a gated property with manicured landscaping featuring dozens of tropical plants and trees. Coconut, Banana, and numerous varieties of palm trees can be found on the property. Key Deer can be frequently spotted nearby. Inside you'll find an "open concept" spacious living room dining/kitchen area featuring a new 65 inch Samsung Smart-TV, full wi-fi/internet access, large

Located in Big Pine Key, Florida, United States. Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters Welcome to Prime Time 2 – Your Charming Waterfront Getaway on Big Pine Key! This delightful waterfront duplex on Big Pine Key offers the perfect setting for quick and easy access to open waters, setting the stage for a relaxing and adventure-filled environment. With ample seawall space, docking your boat is a breeze, and it's just a short ride to enjoy world-class fishing opportunities. Kick back and unwind in the screened porch, where you can immerse yourself in a good book or savor your favorite beverage while taking in the serene surroundings. The Keys lifestyle beckons with numerous activities at your doorstep, and you're just a 40-minute drive from the vibrant charm of Key West and 20 minutes from the attractions of Marathon. Should you require additional space, explore our listing for 'Prime Time,' as both sides of this duplex may be available to ensure a comfortable and memorable

Located in Big Pine Key, Florida, United States. Big Pine Bungalow: Serene Backyard Oasis, Pool/Spa, Expansive Canal-Facing Deck & Pet-Friendly Bliss Welcome to Big Pine Bungalow, a beautifully updated waterfront home where you can immerse yourself in the quintessential Florida Keys lifestyle. Situated on a plugged canal, offering no boating access, this haven provides plenty of opportunities for fishing, kayaking, paddle boarding, and snorkeling right in your backyard. Cool off with a refreshing dip in your private pool or unwind on the back porch, where you can start your day with a morning coffee or savor your favorite cocktail as the sun sets. Big Pine Bungalow creates the perfect setting for relaxation and rejuvenation, allowing you to escape from the everyday hustle and bustle. While there's an abundance of entertainment right at your doorstep, this oasis also serves as a fantastic launchpad for your Keys adventures. Within moments, you'll discover excellent restaurants to satisfy your culinary desires. The vibrant charm of Key

Located in Big Pine Key, Florida, United States. Easy access to beautiful Keys water & a short drive to Key West fun! Easy access to Lower Keys Paradise. Conveniently located on Big Pine Key - close to the bait shop, dive shop. local restaurants, grocery, and a short drive to Key West or Marathon. Our clear, 18' deep, 40' wide canal gives you easy access to the Gulf or Atlantic. The home has a 75' concrete sea wall, fish cleaning station, water & electric, bait freezer and storage available for your fishing convenience. Atter a day on the water, relax under the tiki hut or on the lanai. With 3 bedrooms and 2 full baths, there's room for everyone. Bedroom 1 has a king bed, en suite bath with shower and double sink, and direct access to the lanai. Bedroom 2 also has a king bed. Bedroom 3 has two twin beds and a queen size Murphy bed. Bedroom 2 & 3 share a full bath with shower/tub. Each bedroom has its own tv.The kitchen is stocked with everything you need from a blender to a potato masher. All new appliances include a gas ran

Located in Big Pine Key, Florida, United States. Escape to the Florida Keys to this tropical canal-front home with boat dockage. Escape to a tropical sanctuary at this beautifully remodeled, fully furnished ground level island home located in the Florida Keys. Situated on a quiet street, this home features a bright, open interior with 3 bedrooms, 2 bathrooms. The yard is a tranquil oasis overlooking the canal with a private dock. The canal is on the north side of Big Pine Key which grants access to both the Gulf and Atlantic Ocean. The backyard offers a sense of peace and tropical delight. Immerse yourself in the spa/ hot tub, outdoor shower or just relax under the tiki hut. This home is walking distance to the community park offering tennis courts, skate park, playground, walking trail, basketball courts, baseball field, bocce ball and pavilions along the water. Whether you enjoy boating, fishing, biking or just relaxing in the hot tub, this Florida Keys home can be just the getaway you are looking for. Enjoy all that Big Pine Key

Located in Big Pine Key, Florida, United States. Beautiful Open-Water Property This well-appointed 3-bedroom x 3 full-bathrooms seaside property is on a corner lot with water on two sides. The house faces the open sea (

Located in Big Pine Key, Florida, United States. Excellent boating location-65 ft frontage on deep canal Excellent location 2 bedroom 2 bath home with a 65 ft sea wall on wide canal in Big Pine Key. This is a perfect location for boaters. A marina with fuel docks is located at the end of the canal. Hopefully you won’t need it, but Boat U.S. is across the canal. The canal is the very easy to navigate and less than a 5 minute cruise to the channel. A tackle store is at the end of the street. Outdoor amenities include a locked downstairs storage room, large bait freezer, fish cleaning table and more! Also included are a brand new gas grill, a charcoal grill, 3 kayaks, 2 paddleboards, 3 bicycles and water toys. There is plenty of parking for vehicles and a boat trailer. The location is very convenient with a fuel dock at the end of the and a tackle store just a few houses down from the house. Shopping and restaurants are a short bike ride away.The interior has many windows for views of the canal and is freshly painted. The open floo

Located in Big Pine Key, Florida, United States. Lower Keys Retreat..... This beautiful home located in Eden Pines subdivision on Big Pine Key has the best of everything. Furnished with the finest tropical decor, flat screen TV's, wireless internet and roomy kitchen. Quiet setting, with landscaped yard & Heated PoolThe large living area is spacious and cheery with tall cathedral ceilings. The kitchen is perfect for the group to gather for impromptu celebrations and planning for all the great adventures for the day. The master bedroom on the living area floor has an en-suite bath. Along with a 2nd bedroom and full bath. 3rd bedroom/ living area downstairs has Refrigerator & Coffeemaker, microwave, & Full Bath. The large rear deck overlooks the pool and crystal clear canal. The location is an anglers DREAM, accommodating boats with the 35 feet of dockage, fish cleaning station and large Tiki Hut. Our Retreat will make an ideal vacation spot for the whole family! Only 3-canals to Big Pine channel, no bridges.Additional amenities inclu

Located in Big Pine Key, Florida, United States. Perfect getaway keys Beautifully furnished two bedroom two bath canal home located in Big Pine Key. Fully equipped kitchen with granite counters and stainless appliances, washer & dryer. Master bedroom with king bed, second bedroom has a queen size bed. Sofa in living room converts to another queen bed if needed. There is a nice screened porch overlooking the canal where you can enjoy morning coffee or evening cocktails. Big screen TV and WIFI provided. Bicycles available for you to explore the nice quiet neighborhood and nearby Key Deer Refuge and a kayak and snorkeling gear to enjoy on nearby waters. Lots to do in Key West about 30 minutes west and Marathon about 20 minutes east. Plenty of good restaurants and shopping nearby. Only eight miles to Bahia Honda State Park with beautiful beaches and trails. Bring your boat or rent one. Easy Ocean and Gulf access just down the canal. Fish cleaning station right at the back door and a bait freezer and large capacity ice machine o

Located in Big Pine Key, Florida, United States. Reel Paradise | Fabulous sunsets from this canalfront 2 bed/2 bath on Big Pine Key Cozy 2 bed/2 bath canalfront monthly rental nestled in the natural beauty of the Big Pine Key. Located in the quiet Eden Pines subdivision, boaters will love Reel Paradise's concrete dock and easy access to ocean and backcountry via Pine Channel.All the comforts of home in this light and bright space with canal views on one side and unobstructed wetland and channel views on the other. Gas grill. Inside, the dining table seats 4. Breakfast bar seats 2. Primary bedroom features queen bed, TV and en-suite with shower. 2nd bedroom has 1 double bed and 1 twin bed. Washer and dryer on main level. There are two Roku-enabled TVs set up with YouTube TV live streaming service.Covered porch with outdoor dining for 6. Lockable storage with refrigerator. Room to park one car under the house. Owner's car will be parked under the house during your stay, but there's still plenty of room for your other vehicle, boat trai

Located in Big Pine Key, Florida, United States. Lookout On Long Beach: Discover Serenity at Your Private Waterfront Sanctuary, Amazing Sunset Views! Escape to paradise at Lookout On Long Beach, this secluded waterfront haven, nestled on Big Pine Key, beckons with 100 feet of seawall dockage, inviting you to bring your boat and embark on aquatic adventures. Gather friends and family on the spacious back porch, sipping your favorite cocktails while savoring the picturesque water views and breathtaking sunsets. At Lookout On Long Beach, there's no shortage of activities to enjoy, whether it's swimming, fishing, or simply relaxing by the water. Should you wish to explore beyond this idyllic retreat, you're just a short 15-minute drive from the vibrant offerings of Marathon and a scenic 45-minute journey from the captivating allure of Key West. Your dream Florida Keys getaway begins here at Lookout On Long Beach!At Lookout On Long Beach, we're pleased to offer the option of bringing along your canine companion, allowing you to share your

Located in Big Pine Key, Florida, United States. Manatee Watch | Gorgeous pool, 5 bedrooms, easy ocean access on Big Pine Key Discover your dream waterfront getaway on Big Pine Key! This impeccably updated 5-bedroom, 4-bathroom boating home offers unparalleled luxury and convenience, just seconds away from Pine Channel on the oceanside of Big Pine Key.Nestled just four houses in from Pine Channel, this stunning property features a breathtaking custom pool and spa, perfect for unwinding after a day of exploring the pristine waters. With a 60-foot concrete dock equipped with large piles with fenders, accommodating your big boat has never been easier. Convenient steps lead down into the deep water 70-foot wide canal, providing effortless access for swimming, kayaking, or paddleboarding. And keep your eyes peeled for endangered manatees, frequent visitors to the clear, deep canal.Boasting 2,400 square feet of meticulously designed living space, this isn't your average Keys rental! The main floor features a king en suite with walk-in clos

Located in Big Pine Key, Florida, United States. Sea-Esta | Gorgeous pool home & fantastic boating on Big Pine Key Fantastic boating from this 3 bedroom, 2.5 bathroom canalfront pool home in one of the Lower Keys' best boating neighborhoods, Pine Channel Estates. On a clear, deep canal just a few minutes from the channel, this house gives you easy access to the ocean or backcountry.You'll enjoy a quiet and cool vacation inside this solid concrete home just 30 miles from Key West. It's a light and bright space with warm bamboo floors, high ceilings and large rooms. The primary suite has a large walk-in closet, desk, flat-screen TV, large shower and double sinks. The large second and third bedrooms are separated by a shared full bathroom with shower and double sinks. There's also a half bath and separate laundry room. High-speed Internet and flat-screen TVs available for your streaming pleasure -- no cable TV.Large covered & screened porch with dining and seating areas right outside the main living area's sliding glass doors. Downstair

Located in Big Pine Key, Florida, United States. Gulf-front Big Pine home w/dock Welcome to Tiki Beach House, your exclusive 4-bedroom, 3-bathroom retreat nestled on the Gulf side of the enchanting Big Pine Key in the Lower Keys. Situated on an expansive acre and a half, this newly built haven boasts 150 feet of open water frontage, a private dock, a refreshing pool, and panoramic views that showcase awe-inspiring sunrises over Spanish Harbor and the historic Bahia Honda railroad bridge.The Home:The main level of Tiki Beach House spans 1550 square feet, with an additional 560 square feet in two lofts, providing ample space for relaxation and recreation. The center of the home is the open living room/kitchen space. To each side of the common area are two bedrooms and a bath, along with the third bathroom directly off the common area and a laundry room. The kitchen is well equipped with a large island to bring everyone together for an evening meal or coffee chat for breakfast. Sliding glass doors lead out to the back deck where you

Located in Big Pine Key, Florida, United States. Banana Republics - Located in Paradise Quaint 577 s.f. (1) Bed home on concrete piers. Built in 2015 and also has a balcony and deck. Located on Big Pine Key you are only minutes to the ocean, Key West, and other Florida Keys destinations.

Located in Big Pine Key, Florida, United States. Nature's Paradise - Inground Pool - GREAT MONTHLY RENTAL RATE Contemporary home with cathedral ceilings on corner canal, featuring a 40-foot boat dock with powered davits and 31 foot in ground pool with 8-foot ledge lounger. This home has two levels, featuring the primary bedroom with an en suite and laundry on the first floor, and 2 bedrooms with bathroom on second floor with sliders going out to a deck. Sleeps 8 people. The custom windows highlight the great open floor plan on the first level kitchen/living area. Please note that the Daily rates are for the 28-day min stay. This property is the perfect location for the boater/fisherperson. Head right down the canal and you will be in the Gulf shortly. Come back from a day of boating, if you were fishing there is a cleaning station located on the dock, enjoy a shower in the outdoor shower and then relax in the NEWLY built 31ft pool with ledge lounger. There is a grill outside you can cook your fresh catch on. Enjoy a game of ping p

Located in Big Pine Key, Florida, United States. Cozy canal front home, large kitchen, WIFI, central AC Dream LandersOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to this beautiful waterfront oasis in the heart of the Key Deer Preserve in Big Pine Key, FL. This custom-built 2-bedroom, 2-bathroom house offers a unique opportunity to vacay on a piece of paradise surrounded by conservation land. With unobstructed views of the main canal and easy access to world-class backwater fishing, this home is a true gem in the Florida Keys.Inside, you'll find a well-appointed living space with modern amenities such as Netflix streaming, a fully equipped kitchen, and comfortable sleeping arrangements. Whether you're relaxing on the large terrace, or simply unwinding on the balcony with a view, this home offers something for everyone.Located just a short boat ride from open waters, where you can enjoy fishing for Tarpon, Permit, and Bonefish, this prope

Located in Big Pine Key, Florida, United States. Big Pine Key House 4/2 with 75’ dock and a stunning bay view. 2 stories house with 4 bedrooms and 2 full bathrooms. All amenities included. A 75’ dock and a terrace to a beautiful sunset. Winn Dixie and restaurants in the vicinity. Quiet street and great neighbors.

Located in Big Pine Key, Florida, United States. 2 Bedroom 2 bath Canal front home on Big Pine Key Welcome to 3638 Gulfstream St in beautiful Big Pine Key. This canal front home is turn key and ready for you to enjoy. Custom fully equipped kitchen with bar seating for 4 which leads in to the cozy living room. The spacious bedrooms feature the Master with a King size bed and the Guest Bedroom with a Queen size bed. The exterior features an open porch perfect for soaking in the sun. The downstairs features an outdoor kitchen area and covered seating area that leads to the concrete seawall ready for your water toys to enjoy the beautiful waters of the Florida Keys. Book your stay today you will not be disappointed!!