Florida Keys Condos on the Bay / Gulf Side of the Island For Sale

This beautifully furnished, rental-ready condo offers stunning open water views and direct sightlines to the dock. Already an established vacation rental, generating approx. $40K/yr. thanks to the rare allowance for weekly rentals in this well-maintained condo community. Boaters will love the instant ocean and bay access, with Vaca Cut Channel just moments away. This pet-friendly community features dockage, a heated pool, elevated concrete buildings with newer metal roofs, and new hurricane impact windows and doors. This condo lives like a single-family home with two levels, two private wrap-around balconies, and designated covered parking for three vehicles. Inside, the open floor plan maximizes space and views, with a granite kitchen and sizable island plus a convenient half bath. Upstairs, enjoy two spacious bedrooms and baths, including a master suite with breathtaking Caribbean water views. Come embrace low maintenance living and the flexible lifestyle this condo will afford you!

Great location to all Key West has to offer on this waterfront 2 bedroom, 2.5 Bath Condo townhouse in Bay Villas. Great sunrise views from both first floor and second floor decks. Quiet, private location at the end of Hilton Haven Road. Enjoy the waterfront community pool and assigned parking just outside your front door. The first floor features the kitchen, half-bath and living area with wide open views of the water. Upstairs are the primary and guest bedrooms, each with private bathrooms. Impact windows and sliding doors.

Oceanfront Move-In Ready Home - Coastal Living Awaits! This beautifully updated, bright, and airy two-story townhome offers 2 spacious bedrooms and 2.5 baths, with breathtaking Gulf views from almost every room and on the wrap around balcony.The home is thoughtfully designed with soft coastal hues throughout and a smart, functional kitchen. Both bedrooms are located upstairs, ensuring maximum privacy and comfort. Additional features like impact-resistant glass windows and a durable metal roof offer peace of mind during storms.Enjoy the convenience of a two-car covered parking space and take advantage of being within walking or biking distance to local restaurants. Plus, owners are permitted to have two small pets, making this a truly versatile and desirable home.Located above the flood zone, this home is just steps from the sparkling community pool and private boat dock just off Vaca Cut Channel.Gulfpointe 2 allows short-term vacation rentals (7-day minimum), making it an ideal property for both personal enjoyment and rental income. If youre looking for a low-maintenance, secure, and private community, this is the perfect spot.Whether youre looking for a permanent residence, a vacation retreat, or an income-generating property, this townhome is a must-see. Dont miss out on this opportunity to own a piece of paradise!

Enjoy unparalleled flexibility and luxury with this transient-licensed 3-bedroom, 3-bathroom condo, an exceptional opportunity for a personal coastal escape or a versatile vacation rental. Fully furnished with modern decor, high-end appliances, and meticulous craftsmanship, this turnkey property is poised to impress from the moment you step in. Conveniently located at the entrance to the island of Key West, it offers seamless access to a wealth of shops, dining, entertainment, and recreation options, delivering convenience and enjoyment at every turn. With its streamlined rental setup, this condo is perfect for buyers seeking potential income or for those desiring an upscale island retreat all to themselves with all the amenities one could possibly ask for. Property has two restaurants, a bar, covered parking, mini marina dockage for boating while visiting and a fitness center all on site. Experience the best of refined island living!

Beautifully completely remodeled townhome in the Boaters paradise. 27 assigned boat slip in your backyard! Travertines floors throughout, new plumbing and electric, SieMatic kitchen cabinets and Liebherr refrigerator. There is nothing that needs to be done! Buttonwood features: on site marina with fuel, bait and tackle shop, 3 heated pools, 3 tennis and 6 pickle ball courts, 2 lots for boat railer storage, beach, new gym, library, club house, on site management and 24-hour manned security including manned security gate. Great location, in close proximity to all amenities but far enough to not be disturbed.

Discover your retreat in the Landings of Largo! This upgraded 2-bedroom, 2-bath townhouse boasts stunning Florida Bay views, where spectacular sunsets set the stage for unforgettable evenings. Included is a deeded 30-foot boat slip with a 12k lift, perfect for endless boating adventures.Inside, enjoy custom kitchen cabinetry, impact windows, and doors for comfort and peace of mind. Relax on the spacious screened patio or take in breathtaking water views from the pop-out balcony. Beneath the unit, find ample covered parking and additional storage for all your gear.Nestled in a gated community at Mile Marker 98, this property is a haven for families and boating enthusiasts alike. The Landings of Largo features two sparkling pools, a state-of-the-art marina, a private boat ramp, and beautifully maintained grounds that exude tropical charm. With an active community vibe, youll find endless opportunities to connect and enjoy events or peaceful solitude by the water. This pet-friendly sanctuary welcomes two pets of any size, so you can bring your furry friends along to share in the adventure. Whether youre exploring the nearby coral reefs, indulging in world-class fishing, or simply savoring the coastal lifestyle, Landings of Largo offers the perfect setting. Just moments from local dining, shopping, and entertainment, youll enjoy the best of Key Largo living.Your slice of paradise awaits at Landings of Largo--embrace the vibrant lifestyle and create memories to last a lifetime! This Townhouse is SOLD fully furnished~

Indigo Reef is one of Marathons hidden gem. Nestled in the heart of coastal charm, 23 Indigo Reef is a captivating residence that seamlessly blends luxury with the tranquility of a seaside escape. This immaculate property invites you to experience the epitome of refined coastal living, offering a perfect balance of elegance and comfort.Key Features:Prime Waterfront Location: Situated along the pristine shoreline, 23 Indigo Reef boasts unparalleled views of the azure waters that stretch as far as the eye can see. The gentle lapping of waves and breathtaking sunsets become a daily spectacle from the comfort of your own home.Architectural Splendor: This residence is a testament to architectural excellence. From the moment you enter, you are greeted by an open-concept design that maximizes natural light, seamlessly connecting indoor and outdoor living spaces. The thoughtful layout ensures every room enjoys panoramic views of the surrounding beauty.Coastal Interiors: Step into a world of tranquility. The kitchen is a chefs dream, equipped with top-of-the-line appliances, while the bedrooms offer a tranquil retreat with spacious layouts and breathtaking vistas.Private Outdoor Oasis: The allure of 23 Indigo Reef extends beyond its interiors. The meticulously landscaped grounds provide a private oasis for relaxation and entertainment. Lounge on the expansive terrace, take a dip in the sparkling pool, or unwind in the shade of swaying palm trees - this property is a haven for those seeking the perfect blend of privacy and outdoor enjoyment.Waterfront Lifestyle: Boating enthusiasts will appreciate the private dock, offering direct access to the open waters. Explore the nearby coves, embark on fishing adventures, or simply cruise along the coastline - the possibilities are as boundless as the ocean. BOAT DOCK SPACE SW 31 is slip 26.

Luxury Waterfront Living with Premier Boating Access at Seawatch Condominium. A beautiful 3-bedroom, 2-bathroom residence in this exclusive community. This beautifully appointed condo offers a spacious open floor plan, an upgraded kitchen with granite countertops, Primary bath is upgraded with two individual vanities and large walk in shower. Guest bathroom is upgraded with tile and granite countertops. A large screened-in porch totaling 400 sq ft perfect for enjoying the tropical breeze. For boating enthusiasts, this property is a dream come true. The unit includes a deeded 30-foot boat slip, providing incredibly easy access to both the Atlantic Ocean and the Gulf of Mexico through Vaca Cut channel. Whether youre heading offshore for world-class fishing or exploring the backcountry waters of the bay, navigating between the two is effortless from this prime location. Additionally, the community offers boat barn storage that can house your boat, trailer and other storage items for added convenience. Each unit is assigned a covered parking space. The gated community of Seawatch Condo sits on 17 acres and boasts resort-style amenities, including tennis and pickleball courts, workout room, large pool and spa, and an inviting veranda room for social gatherings. The meticulously maintained grounds create a serene, private atmosphere, making this a perfect retreat for full-time residents or seasonal homeowners. Rental Restrictions: No rentals are allowed for the first two years of ownership; after that, a minimum rental period of 30 days applies. If youre seeking the ultimate Florida Keys lifestyle, complete with luxury, comfort, and unparalleled boating access, look no further. Schedule your private tour today!

Fall in love with the breathtaking bayfront views and stunning sunsets from this beautifully remodeled 2-bedroom, 2-bath condo in prestigious Buttonwood Bay! This direct bayfront unit comes with an assigned 36-ft boat slip (36 x 12.75) and offers the ultimate Florida Keys lifestyle with spacious open-concept living and oversized bedrooms. Step inside to enjoy unobstructed bay views the moment you walk through the door, or dine alfresco on your expansive private balcony overlooking crystal-clear waters. The kitchen boasts granite countertops and stainless steel appliances, making it perfect for entertaining. This condo also features a brand-new A/C unit installed in 2025, ensuring year-round comfort in paradise. Buttonwood Bay is renowned for its luxury, five-star resort amenities, including a newly updated clubhouse with a heated pool, state-of-the-art fitness center overlooking the bay, full-service marina with ethanol-free fuel, and a marine store. Additional amenities include three heated pools, a private beach with a floating dock, six pickleball courts, five tennis courts, a basketball court, a childrens library and play area, a boat ramp, trailer storage, and convenient fish-cleaning stations. This condo comes with an assigned parking space conveniently located near the elevator and seven designated guest parking spots for the X Building. The building has a new roof, and a brand-new elevator will be installed soon, offering even more convenience and peace of mind. Situated in the heart of the Upper Keys, Buttonwood Bay provides quick access to nearby restaurants, shops, and Miami, making it the perfect location for your next home or getaway. Bring your golf cart and start living the Keys life today!

OPEN WATER VIEWS and BREATHTAKING SUNSETS from this Gulfpointe townhome! Enjoy happy hour on the balcony and look for the green flash! Located in a tucked-away community directly of the Gulf of Mexico. Open the impact sliding glass doors on two sides of this corner unit and feel the sea breezes. Move in ready! This spacious two bedroom, two and a half bath condo has new air conditioning, new dishwasher, new bait chest freezer, and granite countertops. The common area amenities include a beautiful pool with a new heater and chiller! Newer impact windows, sliders and front door, metal roof and exterior paint. The community dock can accommodate boats up to 36 feet. Dockage is on a first come, first serve basis with owners having priority. Covered designated parking for three vehicles. Wrap-around balconies on both the main floor and upper floor with stunning Gulf views and the Vaca Cut Channel. The condo complex recently passed State of Florida certification requirements. Spalling repairs completed and no pending assessments. Weekly rental option.

KEY WEST mid town open water 2/2 gem boasting an open floor plan offered turnkey with new furnishings and a deeded 12 X 24 gulf side boat dock. Hilton Haven is a unique neighborhood located mid island on a strip of land that offers a mixed use of waterfront properties on each side. This 8 unit condominium complex is at the end enjoying peace and quiet and also has its own private white sand beach and waterfront pool. Many extras to be enjoyed including tile floors throughout, 2 balconies offer both waterfront and sunset views and an abundance of closet space plus a designated generous storage room for all of your beach/water toys. Property was recently enrolled in a professional monthly vacation rental program. All of this within the city limits of Key West where you will find both nightlife, easy airport access and all of your shopping needs a bike ride or short drive away.

Tranquility and stunning Bay views await! Welcome to Tranquility Bay Resort, located in the heart of Marathon, offering resort-style amenities and outstanding rental capabilities. A rare opportunity for a corner unit, this 3-bedroom, 2.5-bath gulf front townhome is uniquely situated at the quiet, northern end of the resort, yet convenient to all of the fabulous amenities. A perfect blend of luxury and investment with no rental restrictions and a strong rental history.Step inside and be greeted by stunning open bay views from your private porch! Enjoy the extra light from additional windows afforded by the end location. This home comes fully equipped with dishes, linens, furniture, and more, making it truly turnkey. The inviting main level features a spacious living and dining area, a fully equipped kitchen, a half bath, and a balcony that leads directly to the water. Upstairs, the primary suite includes an en-suite bath and a large porch with breathtaking water views, while two additional guest bedrooms, a full bath, and a laundry area complete the second floor.Resort amenities include two pools, a sandy beach, watersports, top rated Butterfly Cafe restaurant, a Tiki Bar, and putting greens, making Tranquility Bay a top destination for visitors. Centrally located in the heart of the Florida Keys, this property is a strong income producer, recognized with multiple TripAdvisor awards.Dont let the sun set on this exceptional investment and vacation home opportunity at one of the Florida Keys most successful & sought-after resorts!

Welcome to a breathtaking beach house in Tranquility Bay Resort, where luxury meets profitability. This 3-bedroom, 3-bathroom waterfront townhome offers the perfect blend of a tropical escape and an income-producing investment.Nestled in an idyllic location just steps from the Gulf and pristine white sandy beaches, this stunning property boasts direct open-water views of the bay. The ground floor features a spacious living area, a convenient half bathroom, and a private porch perfect for relaxing or entertaining. Upstairs, the primary bedroom includes an en-suite bath and a large private porch with mesmerizing water views, while two additional guest bedrooms, a full bathroom, and a laundry area complete the second floor.Tranquility Bay Resort offers an array of amenities, including two resort-style pools, a sandy beach, a tiki bar for sipping cocktails while enjoying stunning sunsets, a fitness center, a Jack Nicklaus putting green, and the award-winning Butterfly Cafe. With beautifully landscaped grounds and endless opportunities for watersports, this is the ultimate destination for relaxation and recreation.As one of the top income-producing properties in the Middle Keys, Tranquility Bay Beach Homes have earned multiple TripAdvisor awards and are a favorite among guests. Owners can enjoy up to 35 days annually for personal use while generating rental income. On-site management handles all operations, providing effortless ownership and peace of mind.This turnkey property is more than a home--its your opportunity to balance personal enjoyment with smart investment potential. Experience the Florida Keys lifestyle, where relaxation and returns meet. Dont wait--your slice of paradise awaits at Tranquility Bay Resort!

VERY RARE CORNER UNIT, Freshly painted inside and out & READY TO ENJOY the Ultimate Keys Lifestyle ! Located in INDIGO REEF, a luxurious town-house style community located directly on the Gulf of Mexico just minutes from the heart of Marathon, yet quiet & tucked away from it all. Situated on over 10 Acres of private land and gated, Villa 25 boasts tons of natural light as an end/corner unit, Incredible OPEN WATER views, vaulted ceilings, quick and easy ocean access through the Vaca cut and an OPEN concept floor plan along with a BONUS room with added square footage on the main level. This OVERSIZED 3 bed/2.5 bath, 1690 Sqft. townhome comes with a deeded 35 ft boat slip located just steps away from the unit. Indigo Reef community offers a spacious HEATED resort style pool with plenty of cushioned lounge chairs, Ice machine, Kayak storage, professional GYM room and ample owners storage located in the temperature controlled HOA building with room for bikes and fishing gear. This home also comes with its own covered parking spot just steps from the front HOA building where more parking can be found along with additional storage on top. This unit comes fully furnished and is a successful weekly vacation rental. Enjoy nightly sunsets while sipping a Key lime margarita from your GULF VIEW unit! You will LOVE sitting under your covered porch while you gaze over the gorgeous BLUE tones of the Gulf & relax after a successful day out on the water. This villa was recently modernized and freshly painted inside and out. Other features include, tile flooring throughout, Large bonus room that could be converted into a 4th bedroom if desired, GRANITE counter tops & STAINLESS steel appliances. SOLD FURNISHED & TURN KEY, ready for you to rent, relax & enjoy the Keys life style all year long. Call today to make this oversized & rare corner/end unit your island dream home!

Bay Harbour condos, located at MM 74.5 on Lower Matecumbe is a very desirable community. BAY HARBOUR ALLOWS 7-DAY RENTALS. Transient Rental License can be obtained from the Village of Islamorada that allows weekly rentals which are restricted in most communities in Islamorada and indeed all of Monroe County. This 2,000 sq. ft three-bedroom, two and a half bathrooms has a view of the sunrise on the Atlantic Ocean. A 30 boat slip is included which allows quick access to Florida Bay and a short ride will bring you to the ocean through channel 2 or channel 5. This gated community boasts a fantastic pool and hot tub along with a gym, clubhouse and tennis courts. Landscaping and maintenance of the property is professionally directed by the on-site property manager. This unit is equipped with propane gas range. Floor plan dimensions in photos are very close estimates. Buyer to verify.

Ideal location in the desirable Bay Harbour community. Convenient access to Florida Bay and the Atlantic Ocean. Community amenities include a pool, hot tub, gym, and clubhouse. Perfect for year-round living or as a vacation rental as Bay Harbour allows 7-day rentals with a Village Vacation Rental License. This condo has a 16,000# boat lift in the designated boat slip.

Paradise awaits you at this beautifully appointed, nautical decor, turn key 3/2.5 townhouse. This Gulfside Villa located at Indigo Reef offers spectacular sunsets right from your back porch and balcony creating a serene and relaxing atmosphere! The 1st floor features the kitchen, dining room, living room and a half bathroom. The 2nd floor will have your 3 bedrooms and 2 baths. The fully equipped kitchen features stainless steel appliances and granite counter tops. The spacious master bedroom has a king sized bed, en-suite bathroom with a double vanity, Glassed in shower and a tub. There is a large balcony show casing endless waterfront views with a brand new trellis. The guest rooms have a queen in one and two twins in the other. The guest bathroom has a tub/shower combo. Your deeded Boat slip which is located straight out from your back porch, can accommodate a vessel up to 31ft in total length. You have fish cleaning stations throughout the new dock area that was completed in 2022. Indigo Reef is a gated community that offers a lush, tropical Florida Keys landscape as soon as you enter the property. Some of the amenities at Indigo Reef include a large pool, a fitness room, a spacious air-conditioned storage area as well as an outside storage area above your carport assigned parking space. This unit is currently in the vacation rentals with a property management company and has existing rentals. If you are looking for an investment property, look no further! All decks and railings are brand new, adding a fresh touch.

Closest living to OLD TOWN with a boat slip!! Peace and quiet and a boaters delight! This small condo complex located in the beautiful Meadows neighborhood has an ordinance against vacation rentals which ensures consistent tranquility with a virtually private pool. One of the only properties close to Old Town where you can keep your boat in the water with an assigned boat slip. With the rising cost of boat slips and marina rates, the slip can save you upwards of a $1000 per month. This third floor 2BR/2BA unit allows for panoramic views of the marina and Key West. The property has had many upgrades during this ownership including new decorative floors with a coastal feel, an upgraded bathroom, new AC, washer and dryer, and some appliances. Enjoy entering a cool car with the covered parking, a rare find in The Meadows. Large private exterior storage space is included. The views are a must see!

Florida Keys Dream! Open Bay Views, Sunsets and Great Ocean/Bay Boating Access ... all in Islamorada! This Futura Yacht Club 2/2.5 townhome includes a 39 ft. deeded boat slip with electric and water just steps outside your door. Futura is truly the Swiss Army knife of Keys communities because it offers one of everything you need, including an onsite boat ramp, onsite boat and trailer storage, spacious pool, two tennis and pickle ball courts, basketball court, shady green space for picnics, and lots of open space for walks and bike rides. The townhomes also allow two pets any size AND the HOA allows weekly rentals. The beach area has a fish cleaning station, kayak and stand-up paddle racks, and owners can now put boat lifts in their slips. If great boating in Islamorada is your Keys dream, its time to wake up in Futura Yacht Club!

Beautiful, comfortable, spacious condominium in historic Delancey Hall. Located on a premier Old Town street a few short blocks from the Key West Seaport and Duval Street (and in the X-flood zone), this condo offers the historic features youd expect from a pedigreed Key West house -- Dade County Pine, crown molding, shutters, wide front porch -- combined with the modern features you need, seamlessly integrated to give you the quintessential Key West experience. Whip up a tasty breakfast in the light-filled kitchen and enjoy it on your large private deck leading to your outdoor shower and the shared pool, or take an easy stroll to Harpoon Harrys or Sarabeths for a little morning pampering. With ample storage and even the option for a one-bedroom lockout, this home serves as the perfect retreat or vacation rental investment property. Its Key West living at its best -- make it yours!