72,107 properties available

Located in Islamorada, Florida, United States. Flakey's B&B in the heart of Islamorada VR-284 A well established, extremely well maintained and family owned and operated vacation rental in the heart of Islamorada. 7 night min stay Saturday - Saturday rental Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Flakeys B&B (Beer & Bed) lol... we do not serve breakfast! In your rental there is a coupon for 2 FREE growler fills downstairs. Thats right, keep your fridge stocked with the freshest beer in the Florida Keys! Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.Walk downstairs and enjoy the freshest craft beer in the Keys, also a huge selection of w

Located in Islamorada, Florida, United States. Serene Sunsets from Your 2 Bedroom Villa Serene Sunsets from your villa! Sandy Pointe is located in prestigious Port Antigua on Lower Matecumbe. This condo is a comfortable two-bedroom one and a half bath, open dining and living room with bar seating to separate the kitchen. Step outside and relax on your private white natural sandy beach looking out into the bay. This beach is known for its unbelievable sunset views.If booking more than a year in advance current prices may not reflect annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. Please note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in

Located in Islamorada, Florida, United States. Best location 3BR house in Islamorada! Pool and beach; walk or bike everywhere. Beautiful updated house on dead-end road with pool and private beach access. Launch a kayak or paddleboard from the beach and explore the shallow, warm waters off the private beach just steps away. Three large bedrooms, each with en suite bath, chef's kitchen with high-end appliances, deck with bbq and ocean views, fully-fenced yard with large pool, tiki hut, and putting green. Located in the heart of Islamorada--walk or bike to all the best restaurants, breweries and shops.Well behaved pets welcome!Available as a furnished monthly rental, or longer lease for a discounted rate.

Located in Islamorada, Florida, United States. Isla Honeydew: 3 En-Suite Bedrooms! Waterfront Resort, Pool, Dock! Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🤝 24/7 Guest supportIsla Honeydew (Villa #1) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is fully furnished, and offers a private deck, and a top balcony with partial water view. This home is fully stocked with everything you need, and a full time Guest Experience Team to assist in making the most of your stay. The Space🛋️ Living Room: Open-concept living area that features ample seating

Located in Islamorada, Florida, United States. Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada 80ft Dock and Boat Lift very close to Islamorada Sandbar and Alligator Reef. Great fishing, diving, snorkeling and boating! 400lb Ice Maker on property to fill your coolers. Large home in upscale neighborhood, very quiet private and peaceful. Tropical views of palm trees and ocean from every window and outside decks. Master Suite takes up the whole third floor with veranda.

Located in Islamorada, Florida, United States. Waterfront Vacation Home w/Stunning Bay/Canal Views, Private Dock, Private Beach Casa KotoOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'With a location right between an attractive canal and a private beach, this stunning three-level, six-bedroom hacienda is exactly what you've been hoping to find for your next family reunion or get-together with friends! You'll have breathtaking vistas of White Marlin Beach from every level, and the two separate wings will afford your group all the space and privacy you deserve during a long and luxurious vacation. When you're not out walking along your private beach, stretch out on the second level's furnished balcony to savor a refreshing beverage while catching up with old friends. You'll have a gas grill for those fun hot-weather barbecues, and there is plenty of seating for everyone to savor the views in comfort. Inside, you'll find a modern and welcoming liv

Located in Islamorada, Florida, United States. Stunning 3 Bedroom Condo with Oceanviews Located in Lower Matecumbe Bay Harbour D-114 - Beautiful modern luxury unit with three bedrooms and two full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room with Wi-Fi also included. The Bay Harbour Complex comes complete with two tennis courts, weight room, pool, your own dedicated boat slip, a fish cleaning station, and Wi-Fi in the community club house. Near the complex is the small Anne's Beach. There are nature trails, boardwalks that lead to small lunch and BBQ areas, private sandy areas hidden in the mangroves and parking. The condo is also near Robbie's Marina (where they feed the Tarpon), Bud n' Mary's Marina and Caloosa Cove Marina. You won't have a problem finding a marina for boat rentals or a fishing guide (Deep Sea or Backcountry). Everything is really close! You are only minutes away from "Downtown Islamorada" where Worldwide Sportsman and the Islamorada Fish Company are located yet you ar

Located in Islamorada, Florida, United States. Isla Lychee: Labor Day Special! Little Basin Villas, Waterfront Boutique Resort, Walkable Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🤝 24/7 Guest supportIsla Key Lychee (Villa #6) is part of Little Basin Villas upscale community of nine luxury vacation villas, located in the heart of the Art District of Islamorada. Boasting a bayside boat dock and private community pool, our villa offers the perfect blend of relaxation and adventure. Enjoy breathtaking sunsets, waterfront views and island décor & foliage. It uniquely offers three bedrooms complete with their own ensuite bathroom, plus a half bath. It is fully furnished, and offers a private deck, and a top balcony with partial water view. This home is fully stocked with everything you need, and a full time Guest Experience Team to assist in making the most of your stay. The Space🛋️ Living Room: Open-concept living area tha

Located in Islamorada, Florida, United States. Coastal Retreat in the Heart of Islamorada Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experience for those looking for a luxurious and private getaway. Each spacious bedroom and en suite bathroom is inspired by modern coastal furnishings. Perfect for entertaining family and friends, including a fully equipped kitchen and an outdoor grilling area. Plus, enjoy the privacy of your own pool and patio that extend from the living area.Please note, this property may be booked for minimum of 28 nights. Currently taking weekly reservations starting November 2024. Please inquire to discuss.

Located in Islamorada, Florida, United States. Unique 2 Bedroom Bay Front Home with Roof Top Terrace 75130 Overseas Highway - Great house in Lower Matecumbe (south side of Islamorada) at the 75-mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. View beautiful sunsets from the screened porch that includes tables and chairs. The roof deck allows for you to see both sides of the island! The bedrooms are located on opposite sides of the house with the common areas in between. Amenities include flat screen tv in the living room, cable television, and Wi-Fi. Dockage is not available at this house.Near the house is Anne's Beach. There are nature trails, boardwalks to small lunch and BBQ areas, private sandy areas hidden in the mangroves and parking. VACATION RENTAL LICENSE: 24-0415 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if und

Located in Islamorada, Florida, United States. Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!! OSPREY BAY VILLA! Wonderful Bay front Home in the heart of Islamorada in the fabulous Florida Keys for rent by the week, or month; offering Incredible Panoramic Bay and Sunset Views. Heated pool & hot tub, sunning decks galore. Deep water dock & boat basin. Elegant, yet casual, spacious living room with coral rock fireplace, wet bar, open dining room, atrium garden,& gourmet kitchen. Sleeps 10-12 people comfortably. Private south wing offers 3 bedrooms; 1 with1 king bed, 1 with 1 queen bed, another 1 with 2 queen beds, and 1 full bathroom with bathtub & separate shower, double vanity sinks etc. Separate bedroom with two twin beds, tv, a/c, etc. adjacent to kitchen. Spacious second level master bedroom suite with king bed & it's own master bath & vanity room, fireplace & bay side veranda. Third full bathroom with vanity and shower downstairs has an entrance from the wet bar/living room area & also exits to

Located in Islamorada, Florida, United States. 3 Lux Ensuites Walk/Boat Island! Summary:Dive into the heart of Islamorada and COUPLES Imagine: THREE MASTER BEDROOMS, so no squabbles over only 1 Master! This 2017 townhome promises restful nights and lively marine filled mornings. From your balcony, salute serenity; Dockside bid sunsets a farewell or mingle with manatees and lobsters. A stroll away: world-class dining, boutiques, bars or a Paddleboard escapade. Welcome to bayside luxury with a splash of fun! Explore the community & nearby libations. Your tranquil Bayside haven awaits

Located in Islamorada, Florida, United States. 3200 square ft. Masterpiece Home Fishing Paradise Waterfront 4 / 3 Islamorada "Monthly rentals only, no split months, thank you."Day 1, of the month , to end of the month.Welcome, to GULFVIEW 150, ISLAMORADA, WHITE MARLIN BEACH"Sports Fishing Capital Of The World" 3200 sq ft. home5 minute walk to White Marlin Beach, from home ! Members only, private key entry, to access beach.Lower Matecumbe, White Marlin Beach, ISLAMORADA, Tri Level 4 Bedroom, 3 Bath home, sleeps 8 to 10You will enjoy the beautiful spacious 800sqf with 16.5 foot vaulted ceiling main room masterfully crafted by gifted carpenters with an open kitchen, new appliances , induction cooktop and *reverse osmosis drinking water filtration , complete with 70" TV internet, cable tv, a pool table, KMP L shape sofa, beautiful Tommy Bahama dining room table that expands to seat 8 - all opening up to 9'x50' back veranda with plenty of seating for your whole group! A wrap around walk way all on the 2nd level, of this beauti

Located in Islamorada, Florida, United States. 7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks Spectacular property - two stories of true keys paradise in a relaxed basin-front setting. Newly renovated, the property has 7 bedrooms, 5 baths, 2living rooms, and a tiki cabana flanking the pool! The house sits on a beautiful basin with deep water that houses many manatees in the heart of the Village of Islamorada! This patch of paradise is less than one minute to open water of the Bayside of Islamorada. Super location – a 1 minute walk to many local restaurants. The island has so much to offer - amazing, galleries, shops, restaurants, aqua blue waters, incredible fishing and boating! Islamorada is an absolute paradise - we love the island and are happy to share the vacation house with guests looking to escape to a patch of heaven in the Keys. The property is exclusively offered as a vacation rental - it is exceptionally clean and easy to enjoy. Designed by award winning Hospitality designers, it has many features

Located in Islamorada, Florida, United States. GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS Contact owner for rates and availability at (305-431-2006).Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' Enjoy deep blue water or back country fishing. Dive, snorkel, and swim on a clear, white, sandy beach (rare in the Keys!). Walk/jog among beautiful waterfront homes. Sip wine while gazing at glorious sunsets while surrounded by coconut palms, Manatees, tarpon, mangrove snappers, and other native fish species. Swim the warm waters at our beach and fish off our dock. Beautiful tropical vegetation, shore birds, and other marine life are all around you. You will cherish the memories of your stay in this 'Island Paradise.' Islamorada Florida is known as 'The Purple Isle' and is located in the heart of the Florida Keys - midway between bustling Miami and laid-back Key West.This charming island home on a deep-water canal features high-beamed ceilings and a 'loft.' The walk-around deck, o

Located in Islamorada, Florida, United States. Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun Happy Tarpon - the best of the Florida Keys and the best of Islamorada! Enjoy privacy in our beautifully renovated home in the heart of Islamorada. It is furnished for easy tropical living inside and out. Swim in the heated pool after a day on the water. Boating, fishing, lobstering, sailboarding, skindiving or canoeing. We have it all. Your boat is right next to the house in our deep-water boat dock. Enjoy a cold drink while you watch the sun set across the Florida Bay. The boat dock holds up to a 28' foot boat in the deep water protected canal. Happy Tarpon is a great place to be between fishing trips or water sports. There is direct access to the Back country and world-class flats fishing or a short run to the Ocean for world-class deep sea fishing. The center-piece of our home is a heated private Pool directly outside of the living room and kitchen. There is a sunning deck/wading area built

Located in Islamorada, Florida, United States. BAYSIDE PARADISE ~ Heart of Islamorada ~ Private Boat Dockage Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle to every place in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and a half bathrooms, to comfortably accommodate up to 6 adults plus children. The bright living area fully opens up to a private patio, where you'll love to gather by the heated plunge pool with a view of the sunset over the bay. Truly in the heart of Islamorada, yet secluded within a protected cove among the mangroves. Less than a mile away from many of the best restaurants, bars and shops in town, including Lorelei, Morada Bay, Chef Michael's, Kaiyo Grill, Green Turtle Inn, Islamorada Beer Company, Florida Keys Brewery, Miss Monroe Boutique and Backcountry Cowboy. The Trading Post grocery store is located within 200 feet and open 365

Located in Islamorada, Florida, United States. Just a Few Friends - Ocean View and Bring your Boat! Experience all the Florida Keys has to offer in this stunning 2 bed/ 2 ½ bath condominium with an Ocean View, located in Bay Harbour, Islamorada Florida. This quiet gated community allows one to truly escape. Have the trip of a lifetime with Just a couple of friends & BRING YOUR BOAT too (up to 30')! Amenities include; Large heated/cool pool, jetted hot tub, fitness center, clubhouse, tennis courts, grills, covered parking + guest parking, and a private boat slip (Insurance required & trailers must be parked off-premises- we can make recommendations for that storage) with power & water giving easy access to both the Bay & Oceanside. The attention to detail in this unit is unmatched. Chic coastal decor, modern appliances, & ocean/pool views allow those staying to truly immerse themselves in the luxurious island life. Enjoy mornings on your private balcony watching the sunrise. Unwind in the evenings watching movies on your massive

Located in Islamorada, Florida, United States. 1 BR Condo Oceanfront Resort and Marina Experience the inviting comfort of our 1-bedroom, 2-bathroom suite, designed as a serene sanctuary for guests. Relax in the bedroom with two queen beds, an ensuite bathroom, and a private balcony. The living area exudes warmth, featuring a snug queen sofa bed, a functional kitchenette, and an additional balcony. While our property enjoys a prime oceanfront location, not all units guarantee direct ocean views.At Caloosa Cove Resort, enjoy breathtaking vistas, a heated swimming pool, a serene beachfront, a convenient General Store, boat slips, and exciting boat charters. With a variety of activities nearby, it's the perfect destination to unwind and fully immerse yourself in the captivating ambiance of Islamorada. Our onsite marina offers boat slip rentals and charters for adventurous guests. Additionally, a private beach and large, heated pool provide relaxation options.

Located in Islamorada, Florida, United States. Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new flat screen HD TVs in living room, master and queen guest! Gourmet kitchen has granite countertops, stainless steel appliances and a great selection of cookware and utensils. Open floor plan with wet bar and formal dining room. Enjoy your morning coffee or afternoon cocktail with the gentle ocean breeze on the wonderful screened in water front balcony. This unit is the model for all of Bay Harbour and is professionally decorated and furnished.The condo includes all linens and is equipped with a full washer and dryer. Also included is the use of a 50-foot boat slip in a protected harbor with four-foot control depth. The large screened in balcony looks

Located in Islamorada, Florida, United States. Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing getaway, look no further. Relax with the family in this cozy Island retreat. Completely remodeled! Come enjoy the community heated pool and a morning bike run. Enjoy the Florida Keys with your own private backyard and private parking.

Located in Islamorada, Florida, United States. DELUXE ISLAMORADA PENTHOUSE CONDO WITH 50' BOAT SLIP AND 25,000# LIFT This stunning top floor end unit in Bay Harbour with ocean and harbor views also includes a 50' boat slip with Boat Lift! The interior design is spectacular. Coffered ceilings in the living area, top of the line Miele and Thermador appliances, custom kitchen cabinetry, intricate tilework in the baths exceptional views from all common areas and primary bedroom. The Bay Harbour complex amenities include a pool, spa, gym, tennis courts and a clubhouse for friendly gatherings. Covered parking and a ground level storage unit are also included.

Located in Islamorada, Florida, United States. Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Family Compound. This Beautifully renovated Compound / Property Comes With A recently completed Magnificent Landscape Oasis , That Begins With Coral Stones And Fire Bowl Entrance To A Large Golf Putting Green For Everyone In The Family To Enjoy ⛳️, Plenty Of Shaded Areas With Palm Trees 🌴 , A Fire Pit and Hammock area With Confortable Sittings that’s just perfect For Family Gatherings and fishing stories , (including the one that got away) and/or just total relaxation . and Much More . Truly The Perfect Vacation Home For Any Size Family. .Has 3 distinct Sleeping Quarters ,one in the Upper Floor Home ( This Spacious And Accommodating 2nd Floor Suite have its Own Entrance ,King Size Bed , Small Fridge/ Microwave Oven , Nespreso Coffee Maker , Sitting Vanity With Mirror , A 65 In TV And A Large Confortable Scenic And Relaxing Wrap - Around Balcony ). On Ground Floor and With Access from the Swimming Pool Area ,you’ll find Entra

Located in Islamorada, Florida, United States. Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK Plaza Del SolOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to the Keys for a serene stay at this family-friendly home, sitting waterfront right on a canal and boasting its own dock. Wake up with a sunrise coffee on the wraparound deck each morning, then slip into the provided kayak for a quiet paddle. Or, spend the day deep-sea fishing - a private boat ramp and watercraft floating ramp are just a short drive away. Beach bums will love having access to a one-half-mile-long private, white-sand beach, but if you’d rather stay dry, all the shops, restaurants, beach bars, and amenities of Islamorada are just a short drive away. The world-famous Seven Mile Bridge is around 28 miles further down the Overseas Highway. At home, you’ll find a bright, open living space on the main level, featuring coastal decor, high ceil