58,368 properties available

Located in Islamorada, Florida, United States. Enjoy a Hassle-Free Stay! Free Parking, Onsite Pool, Near Anne's Beach Discover island adventures with us! Explore Islamorada’s beachfront, soak in Alligator Reef Lighthouse views, or dive into water sports. Enjoy nearby attractions like Anne's Beach, Theater of the Sea, and the History of Diving Museum.Experience a slice of paradise in this authentic room at our boutique beachfront resort! We offer a private lounge on the beach where you can relish the authentic island life experience. Enjoy a bike tour through the island, an outdoor pool, and a sun terrace with breathtaking views of Alligator Reef Lighthouse. Embark on boating excursions and dine at our delightful American restaurant. Relax, rejuvenate, and explore the serene beauty that awaits.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of $100/night/unit on the credit/debit card provi

Located in Islamorada, Florida, United States. Charming Beach Front Home in Lower Matecumbe 113 Sunset Drive - Come and stay in this adorable "beachy backyard" home located on the crystal-clear Atlantic Ocean! This home truly has an amazing water frontage. The home has plenty of room for your whole family to relax, having two bedrooms upstairs and two bedrooms downstairs! Near the house is the small Anne's Beach. There are nature trails, boardwalks to a small lunch and BBQ areas, private sandy areas hidden in the mangroves and parking. The home 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 close! You are only minutes away from "Downtown Islamorada" where Worldwide Sportsman and the Islamorada Fish Company are located yet you are in a quiet area of town. Islamorada Vacation Rental License Number- 24-0387 Per Islamorada's vacation rental ordinances for weekl

Located in Islamorada, Florida, United States. Port Antigua Canal Front Home & Private Beach Get away on Island Time to beautiful Islamorada. Our home is in a lovely quite subdivision with the most beautiful private beach in the FL Keys. Enjoy a screed in porch overlooking the back yard and canal. The screeded in porch has a 6-person dining table, lovely sitting area at the other end. Another open patio is ground level with lots of cozy seating & Grill. Each bedroom has its own access to the porch. A private boat ramp available to launch your boat with some of the best fishing in the Atlantic just minuets away. Plenty of great dinning and actives, many accessible by boat. Property does not come with use of boat lift, minimum space provided for your personal boat.

Located in Islamorada, Florida, United States. Opulent waterfront estate with dock, pool, hot tub & rooftop view - dog-friendly Waterfront WonderOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Swim right up to the edge of luxury at this ultra-private waterfront mansion. Located on one of the most prestigious streets in the Villages of Islamorada, this family-friendly property sits on a sizeable deep-water lagoon with protected boat dockage. Enjoy immaculate indoor/outdoor entertaining space, including wraparound screened balconies with alfresco dining, a heated pool, hot tub, and a fantastic rooftop -- all offering breathtaking vistas.The opulent interior boasts keystone walls, marble flooring, soaring ceilings, and two full kitchens. The chef’s kitchen adds to the grandeur and is fitted with custom cabinets, granite countertops, and stainless appliances like a Sub-Zero fridge and a six-burner gas stove. Sprawl out between three beautifully appo

Located in Islamorada, Florida, United States. Bay front 6BDr Private Beach Pickle-ball Ct Game room Sunset Views This absolutely spectacular bayside estate is available for rentals to the public for the first time. Recently upgraded this 6 - bedroom 5 bath estate will be your gateway to creating memories lasting a lifetime. Newly renovated bathrooms - state of the art kitchen - brand new floors - this is basically a new construction gorgeous estate - this amazing property is located just south of the iconic Robbie's Marina - nestled on 2 acres.*Game room*Ping pong table*Foose ball*Dart board*Poker table*Private pickle ball court*Basketball court*Beach volleyball court ***all courts have lights for night play****Charcoal BBQ*Propane BBQ*Smoker*Fishing off dock*The most memorable Sunset Views in the Florida Keys*Two Tiki huts* Paddleboards*Kayaks*Pools Toys*Wi-Fi*Multiple Big Screen TVs*Gym EquipmentWe offer additional amenities upon request including *Organizing fishing trips*Snorkeling trips**Leisure trips*Sunset boat tours*sandba

Located in Islamorada, Florida, United States. A True Islamorada Oasis with Breathtaking Bay Views Little Bay Compound - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. The Upper & Lower Duplex are each 1,500 sq ft units, each with two bedrooms, two full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the bay. Each unit accommodates 6 people (upper master bedroom: king and twin murphy, Guest bedroom: two twins, sofa sleeper) (lower master bedroom: queen and twin murphy, guest bedroom: two twins, sofa sleeper)The Cottage is a bright and airy 1,250 sq ft unit with a huge master bedroom (king & sofa bed), 2nd sunroom with sofa bed and twin murphy bed, two full baths, laundry room, and combined family room, kitchen, & great room. The Cottage accommodates 6 people. All units come equi

Located in Islamorada, Florida, United States. Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and Wi-Fi. The condo boasts some amazing views of the Clear Blue waters of the Atlantic Ocean looking over Sea Oats Beach. Relax on your own private roof top patio and enjoy a beautiful sunrise of the glow of a famous Florida Keys Sunset. NOTE: Onsite trailer parking is not allowed at Bay Harbour community. VACATION RENTAL LICENSE: 24-0309 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.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 proceedi

Located in Islamorada, Florida, United States. Feel the breeze of the keys **HOUSE HAS BEEN RENOVATED AND PICTURES TO COME**Perfect Vacation Home in Islamorada, the center of the Keys Island. The house is ideal for a large family get away, or a small intimate escape. It is perfectly situated between canals providing guests with an unforgettable keys breeze. You are conveniently located near supermarkets, restaurants, and fun activities, like Theatre of the Sea. Take a walk to the community private beach which is only accessible through key access. The house is equipped with 75 total dock space with approximately 35 feet of that dock space to accommodate your boat. It has been updated with a new pool and resort style yard for your enjoyment. Beautiful open views and quick access to ocean. The house is located in one of the most well known fishing areas, Islamorada, renowned for the best fishing areas.

Located in Islamorada, Florida, United States. Your Key to Unforgettable Island Moments! 2 Relaxing Units with Balcony! Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of the guest rooms and suites in our three-bedroom house is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual elegance of the tropics with our resort amenities. Guests have access to all the amenities they might possibly need right on the premises, including a restaurant, bar, swimming pool, and slips for those visiting with boats. But if you want to venture offsite, we have a shuttle service that can take you around.PLEASE NOTE:- These are TWO separate rooms. Rooms are individually unique and may not be adjoining or adjacent, allocated based on availability upon arrival. The price is for all rooms.- The property requires a damage deposit of USD 100/ni

Located in Islamorada, Florida, United States. 1 bedroom unit with a nice view of the Florida bay. PROPERTY NAME: The Palms #31779901 Overseas Highway, Islamorada, FLLOCATION: Bayside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful sunshine. This one bedroom unit has partial views of the ocean and a good view of the Florida Bay. It is perfectly proportioned - large living area and large bedroom and dressing area with separate linen closet and walk-in closet. The kitchen and baths have been updated. You'll be glad you chose this unit for your holiday in the Keys. Bedding is king and queen sleeper sofa. This property is professionally managed by Keys Holiday Rentals.Sleeping Arrangements: Sle

Located in Islamorada, Florida, United States. The Villa by the Bay, Islamorada FL Take your heart, family & fishing gear to the blissful Villa by the Bay! Quaint gated 8 homes; Coral Cove is centrally located in Islamorada. The best deep-sea fishing awaits! Ocean access, heated private saltwater plunge pool with wonderful waterfalls. Balcony allows the beautiful sunset & wonderful breezes. Enjoy walking distance to the best restaurants & bars. Community pool & dock. Beautiful sunsets await overlooking the bay. Private dockage (Upon request/fee) Ready set book! Initial supplies provided such as coffee, paper towels, toiletries for each guest. Thereafter we ask additional usage supplies needed are responsibility of guest

Located in Islamorada, Florida, United States. Zesty Lower Matecumbe Condo with Private Beach & Dockage It's not every day that you come across a rental like this. This delightful and fun 2 bedroom, 1.5 located in Lower Matecumbe offers a private beach, dockage, and enough charm as you can squeeze in. The main living space, located on the second floor, has a great open layout making it the perfect space to both entertain and unwind after a long day on the water. With wall-to-wall windows, peekaboo bay views, lively and fun décor, charming wood accents this condo is the perfect home away from home. The third floor offers a guest bedroom with two twin beds, bathroom, and master bedroom with a cozy reading nook and windows with the perfect bay view. The laid-back yet eclectic vibe of this home is gratifying to all and must be experienced.Enjoy your own little slice of paradise from the beach. One of the very few beaches in the Florida Keys, Sandy Pointe offers soft sand, crystal clear waters, and the best sunsets on the island. Feelin

Located in Islamorada, Florida, United States. Beautiful Oceanfront Oasis with Pool Sea Ranch - Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in the beachside pool. The front home sits waterfront with two bedrooms and two bathrooms. The cottage sits back on the property with two bedrooms and one bathroom. Entertain in the pool room with pool table, wet bar, poker table and more. The ocean front paradise is also a 'Destination/Wedding Location!' $8,000/week & $24,000.00/month. The viewing dock is just that, it is too shallow for boats, so boats are prohibited. 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 re

Located in Islamorada, Florida, United States. Picturesque 2 Bedroom Condo with Fabulous Ocean Views. PROPERTY NAME: The Palms #40479901 Overseas Highway, Islamorada, FLLOCATION: Bayside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: This is an exceptional 2 bedroom and 2 bath condo located in one of the most popular Islamorada condo complexes - The Palms of Islamorada. The balcony is large enough to dine or recline and offers fabulous open water views. While sipping coffee in the morning you can watch the fishing charters and dive boats go out for a day's adventure. Later in the day enjoy the view as they return. Gazing at the Atlantic Ocean and Alligator Reef Lighthouse will provide hours of relaxation. Inside, you'll love the comfortable furnishings and convenient floorplan of this condo. The master suite offers sliding doors to the balcony, king bed, walk-in closet and an ensuite bath. The second bedroom features twin beds and large closet. T

Located in Islamorada, Florida, United States. Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access! Welcome to the "Keys Life Cottage!"This beautifully updated and spacious two bedroom, one bath home is tucked away on a large landscaped lot in the heart of Islamorada and within walking or biking distance to Islamorada's famed Arts and Cultural district and to some of the most renowned restaurants, breweries, marinas and boutiques in the Florida Keys. Between the high vaulted ceilings, open floor plan, fully equipped kitchen, gorgeous bathroom, inside laundry, BBQ, cable and internet, it’s easy to make yourself right at home! The primary bedroom is equipped with a queen size bed, the second bedroom has a twin bed and there is also a queen sleeper sofa in the living room for additional guests. Included in your stay is access to a private members only club (only 1.5 miles away!) that offers a peaceful, secluded sanctuary complete with a heated and chilled pool, tiki bar, and tournament rated fishing captains available fo

Located in Islamorada, Florida, United States. Isla Key Acaí: Waterfront Boutique Resort, Htd Pool, Dock, Walkable Short Description🏡 Community amenities: heated pool, boat dock, BBQ📍Walk to shops, grocery store, parks, restaurants🛏️ All bedrooms feature ensuite bathroom 🐶 Dog friendly 🤝 24/7 Guest support teamIsla Acai (Villa #8) 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 featur

Located in Islamorada, Florida, United States. Beachfront Cottage - Islamorada! Immerse yourself in the tranquil beauty of this fully updated beachfront cottage in the heart of Islamorada. Enjoy the chef's kitchen, appointed with Wolf stove and subzero refrigerations. Soak up warm hundred-year-old reclaimed teak floors, and relish the ocean views from every room. All new furnishings, including a sofa sleeper with gel infused memory foam for maximum comfort. Embrace water activities including snorkeling off your own beach, and beach games, paddleboard, and kayak included plus bicycles. Just be aware that construction noise may occur from time to time from the neighboring property, though the impact windows and doors ensure a peaceful interior. Access the retreat through the private estate gate at 209 Carroll Street.

Located in Islamorada, Florida, United States. Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated. Escape to paradise in the heart of Islamorada, the fishing capital of the world! This stunning 4 bedroom home sleeps 8 and offers a tranquil retreat in a quiet, secluded, private community. Enjoy the heated community pool, boat dock, and private boat ramp. This home has plenty of parking and its own commercial ice machine, and is a boaters dream. Indulge in great shopping and restaurants nearby, and don’t miss the chance to snorkel or paddle board in the natural aquarium just off the dock. Unwind on one of the beautiful porches surrounded by nature and watch the birds dance across the sky. Your island paradise awaits!

Located in Islamorada, Florida, United States. Charming Condo in Paradise! Take a break & unwind at this charming Islamorada gem! Let this 1/1 bright & homey condo be your needed getaway to paradise. Take advantage of Islamorada’s breath taking waterways with access to the private boat ramp & dock with cleaning stations, water, electric, & trailer parking at first come/serve for a boat up to 25 ft in length. 300k liability insurance required for boat docking. Nothing beats bringing your fresh catch home to cook in the full kitchen! Enjoy the community amenities including the pool, pickle ball/tennis court, shuffle board, sitting area, & tic tac toe. Feel free to do laundry in our private in condo 2-in-1 washer/dryer. Condo is located on the 3rd floor with stairs on each end of the building. Condo equipped with coffee station, filtered drinking water spout, dining table for four, large fridge, smart tv, pull out couch, memory foam king bed, walk in closet, & private balcony with sitting area. At MM76 The location of this condo is ev

Located in Islamorada, Florida, United States. Harbor Hideaway | Island style beach house with pool, dockage & bay views! Introducing “Harbor Hideaway!”This charming, island style beach house on Lower Matecumbe Key is the perfect spot for your next Florida Keys vacation. This home can sleep up to 11 guests, with 4 bedrooms and 2 1/2 baths. The main living space features a fully equipped kitchen and an open floor plan with vaulted ceilings, tons of natural light and water views. This home is also equipped with high speed WIFI and 4 Smart TV’s offering Xfinity cable, Netflix, Amazon Video, Disney + and YouTube TV. The oversized wrap around porch has been freshly painted and offers a gas grill, lounge seating, stunning sunset views, and an additional dining table to enjoy meals or cocktails “Al Fresco.” The main level features three bedrooms and two full baths that were fully renovated in late 2021 and feature luxury fixtures and finishes. The master bathroom features double sinks, an oversized shower with dual shower heads and a free

Located in Islamorada, Florida, United States. Best Location! Beachfront Property with Outdoor Pool, Pets are Welcome! Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential

Located in Islamorada, Florida, United States. Islamorada | Maison Residences Welcome to Maison Residences, your exclusive 4-bedroom, 4.5-bathroom haven for the perfect oceanside holiday retreat. This residence boasts an open floor plan with a grand room and expansive living terraces, inviting you to embrace the laid-back elegance of seaside living.After soaking up the outdoor delights, retreat to your private elevator, whisking you away to an airy oasis with oversized windows framing breathtaking views of the ocean and pool. The gourmet kitchen, equipped with top-of-the-line Sub-Zero and Wolf Gas appliances, beckons for culinary adventures. The casual island seamlessly connects the kitchen to the dining area, fostering a convivial atmosphere for gatherings.Entertainment takes center stage in the grand room with 9-foot stacked sliders leading to expansive terraces. Here, multiple seating areas, a large flatscreen TV, a fireplace, and an infrared/gas grill set the stage for unforgettable moments.

Located in Islamorada, Florida, United States. Unity & Autonomy 2 sides a Beach Duplex & 70' DOCK Summary:This is for BOTH upstairs sides of the duplex the whole upstairs of the house can be rented through here so that you can Enjoy the keys life in style living in this beautifully furnished 4 Bedroom (2 on each side), 2 Bath (1 on each side) , 2 kitchens (1 on each side), canal front retreat w/room for boats at the private 70' large concrete dock with attached fish cleaning station which is an obvious necessity in the Keys & easy access to the bayside or oceanside. The boats are available to rentThe Space:property is currently receiving a pool installation to be completed by end of September 2020This listing is for BOTH upstairs sides of the duplex. Downstairs is available as an add-on should you need an additional three bedrooms one bathroom Downstairs (link below). Upstairs Each side of this luxury duplex you will have peekaboo views of the ocean and comfortably accommodates with two queen beds and one queen convertible sofa on

Located in Islamorada, Florida, United States. Casa Del Pirata | 3 bed / 2 ba Canal Home in Islamorada Welcome to Casa Del Pirata! Located in the heart of Port Antigua, this canal front home boasts tropical vibes and can accommodate up to 6 guests to experience the “island life style.” Inside you will find an open living space permitting endless entertaining, a fully stocked kitchen with everything you need for home cooked meals, dining area for four, living room with an oversized sectional sofa, smart TV with cable and wifi, laundry room with a full-size washer/dryer, three bedrooms (one king, two queens) and two full bathrooms. Step outside to the large screened-in back porch and sip your morning coffee while watching the boats go by, or grill your catch of the day while the sun sets and lights up the sky in hues of orange, pink and purple. Biscayne Blvd is one of the few streets that backs up against our protected mangroves and provides extra privacy that other canal front homes can’t offer. The spacious downstairs area offers a