Distance to beach: 3 miles to Anne's Beach State Park
Key Amenities
About this property
This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your ...
Property Type
Islamorada House
Featured review
All I can say is that this place never fails to impress! The views from every inch of the property are the best in all of the keys! Great communication with Rich and his office. Would recommend every ...
Distance to beach: 2 miles to Founders Park
Key Amenities
About this property
Welcome to your dream getaway in Islamorada! This 3-bedroom, 2.5-bath paradise boasts a gourmet kitchen with a Viking gas stove, a spacious dining area, and Internet-ready TVs for game days or movie nights. On the first floor, you will find two bedrooms, a full bathroom and a large entertainment area ...
Property Type
Islamorada House
Featured review
We had a wonderful time here. The location is perfect. Close to restaurants, shops, and attractions. We spent a lot of time floating and frolicking in the canal. The house was spotless. The kitchen was ...
Key Amenities
About this property
''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house ...
Property Type
Islamorada House
Featured review
By far and away, this was the best rental property we have ever stayed! We have been visiting Islamorada for nearly 20 years and have stayed almost everywhere you can imagine, and we have now struck gold ...
Distance to beach: 0.5 miles to White Marlin Beach
Key Amenities
About this property
Bring your boat and Jet Skis Nestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, double jet ski lift, and two floors facing ...
Property Type
Islamorada House
Featured review
We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has ...
$489
avg/night
Key Amenities
About this property
This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.
Property Type
Islamorada Condo
Key Amenities
About this property
Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...
Property Type
Islamorada Condo
Featured review
I highly recommend this vacation spot. Not only is the condo very nice the whole property is set up for your every need. The owner and property manager are very nice and accommodating. I was amazed by the ...
Key Amenities
About this property
ALERT: BRAND NEW POOL JUST COMPLETED AND INSTALLED.... DOWNSTAIRS IS AVAILABLE TO RENT BUT IS NOT INCLUDED IN THE PRICE feel free to ask about downstairs pricing and availability. Downstairs is an additional 3br and 2ba so the upstairs and downstairs would be a total of 7br & 4ba.... THIS LISTING ...
Property Type
Islamorada House
Featured review
My wife and I spent the month of Dec. 2022 at this property in Islamorada (HEAVEN) in the Keys. The property has a pool, a canal and a boat dock that can handle any boat. Let me start of saying that ...
Distance to beach: 1 miles to Anne's Beach State Park
Key Amenities
About this property
This Condo sleeps 4 and comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key, Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks. Newly refurnished and refurbished, ...
Property Type
Islamorada Condo
Featured review
This two bedroom apartment in the beautiful Bay Harbour condominium was special. The views of the ocean and the apartment complexes marina were exceptional. The apartment was well stocked with all the cooking ...
Distance to beach: 2 miles to Founders Park
Key Amenities
About this property
This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios ...
Property Type
Islamorada House
Featured review
If you’re looking for a well kept beautiful home, right on the water positioned right between the Gulf and Atlantic, great pool and hot tub YOU FOUND IT. Communication is great and owner is so helpful. ...
Key Amenities
About this property
Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking ...
Property Type
Islamorada Townhome
Key Amenities
About this property
The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assigned boat slip in private marina just around the corner. All new kitchen, baths, porcelain tile flooring, fully furniture and LOTS more. Three bedrooms, two bath home on a peaceful plugged ...
Property Type
Islamorada House
Key Amenities
About this property
1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community ...
Property Type
Islamorada House
Featured review
Here is the review I am trying to post via for our March 2024 stay. Wonderful! Fantastic! Amazing! Wonderful Hosts!!! Jay and Sharon are so welcoming and supportive! We felt at home before we ...
Key Amenities
About this property
Welcome to Mother Ocean! This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room ...
Property Type
Islamorada Condo
Key Amenities
About this property
Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys. Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance. 2 ...
Property Type
Islamorada Condo
Featured review
Plantation by the Sea is an older condo complex that is beautifully maintained. The condo is located at MM 87.5 just off of U.S. 1 in the heart of Islamorada. Restaurants of various types can be found within ...
Key Amenities
About this property
Welcome to your private slice of paradise in the heart of the Indian Waterways! This newly constructed Coastal Contemporary Caribbean-style home, with 165 feet of waterfront, invites you to experience the ultimate blend of luxury and tranquility. Unwind in Style: From the moment you step into the ...
Property Type
Islamorada House
Key Amenities
About this property
Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada ...
Property Type
Islamorada House
Featured review
A well maintained home in a perfect quiet setting. The owner Patrick was outstanding to work with and made sure that all was in order. He is an excellent communicator. Welcome bottles of wine greeted us. ...
Key Amenities
About this property
Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...
Property Type
Islamorada Condo
Key Amenities
About this property
A beautiful piece of serenity and paradise can be yours, available for seasonal rental from January through April. Islamorada the fishing dream of all sport and causal fishing enthusiast. But if you don't fish (that is a shame) you can enjoy the wonderful dining, the historic parks, diving and ...
Property Type
Islamorada Condo
Key Amenities
About this property
This condo is located in one of Islamorada's most prestigious condo complexes. PROPERTY NAME: Beacon Reef #407 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 83.2 DETAILS: ...
Property Type
Islamorada Condo
Key Amenities
About this property
This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished. Upstairs ...
Property Type
Islamorada House
Featured review
This was a perfect house! Easy and quick access to ocean and gulf, docked 35’ boat right at the house, large pool with hot tub, plenty of parking for vehicles and trailers, very clean, well stocked, tiki ...
Key Amenities
About this property
This condo is located in one of Islamorada's most prestigious condo complexes. PROPERTY NAME: Beacon Reef #414 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 83.2 DETAILS: ...
Property Type
Islamorada Condo
Key Amenities
About this property
This Condo is located on Lower Matecumbe Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Bay Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a second floor location make it easy to enjoy your stunning view ...
Property Type
Islamorada Condo
Featured review
We have rented a condo at Bay Harbour for many years now. We love the location and the complex amenities. I fish a lot so my husband is happy with the workout room, pool, safe bike paths, hot tub and ...
Distance to beach: 100 feet to Front door
Key Amenities
About this property
MINIMUM STAY: 30 days Spacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip. Walk out your front door and go boating. You’ll ...
Property Type
Islamorada Condo
Featured review
Priceless view of the ocean. Nice marina. Workout room is great with a view. The condo is clean and spacious. Every thing you need is here. Very easy to maintain. During my 3 month stay from May to August ...
Key Amenities
About this property
Beautiful views from this condo! Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL. We are new owners of this condo that has never been in the rental pool. (that is why few reviews) Complete remodel with no expense spared! The location is quiet with the most beautiful ...
Property Type
Islamorada Condo
Distance to beach: 0.5 miles to White Marlin Beach
$643
avg/night
Key Amenities
About this property
House, 3 Bedrooms, 2 Baths, Sleeps 6 Pure High End Luxury with all the Bells and Whistles Boat Friendly Vacation Rental with Dock Villa Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. ...
Property Type
Islamorada House
Featured review
This was a spectacular vacation! The house was clean and comfortable, and the location was quiet and the setting perfect. I could write a novel about the host and the house, but in a few words the host ...
Distance to beach: 50 yards to Private sunning beaches at Anglers
Key Amenities
About this property
SAVE VRBO's $500-600 Booking fee!! Welcome to Anglers Reef, a very special community of vacation homes. And to Anglers Reef 140's OceanFRONT location with its unique UNOBSTRUCTED OCEAN VIEWS FROM EVERY ROOM and spacious wraparound decks! Boat slip is optionally available for $375/wk, Christmas ...
Property Type
Islamorada House
Distance to beach: 5 miles to Anne's Beach
Key Amenities
About this property
The "Nest" villa (one of 7 privately owned condo residences) sits on a 1 acre lot located on Islamorda's beautiful Florida Bay. Stunning water views and unforgettable sunsets are guarenteed. The property is filled with mature tropical landscaping along a tree lined private gravel driveway ...
Property Type
Islamorada Villa
Featured review
My 18 yr old son and I stayed here at the end of September and it was a fantastic trip! We have been going to the keys for 14 years several times a year. This unit is the cleanest we have ever seen! ...
Key Amenities
About this property
Welcome to Caribee Beach House! Discover the enchanting charm of Caribee Beach House, where the timeless allure of old-school Islamorada beautifully melds with stylish comforts. Tucked away in the heart of downtown Islamorada, this hidden gem offers an extraordinary retreat with 200 feet of private ...
Property Type
Islamorada House
Distance to beach: 0.5 miles to Port Antigua Private Beach
Key Amenities
About this property
This recently renovated property enjoys 6 bedrooms, 4 bathrooms and separate kitchens, living rooms and laundry facilities. It shares an ocean facing veranda with 2 dual gas grills and multiple seating and lounging areas. It has ample offstreet parking for vehicles and trailers. The Admiral on the Cove ...
Property Type
Islamorada Townhome
Featured review
We enjoyed our stay at this beautifully furnished and well stocked house. George and Bonnie responded quickly to any questions that we had. The separate living areas allowed us to enjoy family and friends ...
Key Amenities
About this property
The apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape. ...
Property Type
Islamorada Apartment
Featured review
This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under ...
Key Amenities
About this property
Welcome to Paradise Palms! Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-bath home serves as an excellent setting for your tropical getaway. Ideally located in Islamorada on Lower Matecumbe Key, you will have convenient access ...
Property Type
Islamorada House
Distance to beach: 0.3 miles to Anne's Beach
Key Amenities
About this property
Enjoy this modern lagoon front ground-level one-bedroom apartment in a single-family home with exclusive use of backyard, pool, dock, and carport. Located on the Gulf side of Lower Matecumbe (Islamorada MM 73.5), minutes from the Channel 2 and Channel 5 Bridges, offering immediate access to the Oceanside. ...
Property Type
Islamorada House
Featured review
this property was great for us as an older couple....park under cover steps from the front door..beautiful pool and canal front and a quiet location. the home is clean and easy to care for and the owner ...
Key Amenities
About this property
Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located ...
Property Type
Islamorada Townhome
Featured review
Excellent couple to work with. Great communication. The rental was beautiful and clean. We had a problem with the rental and they communicated with us and together we solved the problem. They went over ...
Distance to beach: 100 yards to Port Antigua Private Beach
$351
avg/night
Key Amenities
About this property
Book Your Winter Getaway! This spectacular 3/Bed 2/Bath canal front home is located in Lower Matecumbe Key, a part of Islamorada island. Enjoy the exclusive neighborhood of Port Antigua—just a 5 minute walk to our private beach. The house is nautically designed, with a spacious and open floor ...
Property Type
Islamorada House
Distance to beach: 4 miles to Anne's Beach
Key Amenities
About this property
Enjoy the sunrise from the balcony or from in the condo through 50 ft of glass sliding doors. You can also see the sunset from our walkway on bayside. We have a full kitchen from dishwasher to microwave, washer/dryer, even beach towels. We have wifi, cable TV, and a Master Bath with whirlpool tub, ...
Property Type
Islamorada Condo
Featured review
We had a fabulous time at this condo. Spectacular views, great fishing. Close to EVERYTHING. The condo was spacious and VERY CLEAN. EVERYTHING you would need for a fun time was here.. will be back again ...
Key Amenities
About this property
4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family-friendly and a fisherman's dream. Our home sleeps 8 with every comfort you would want while on vacation in the keys...Large ...
Property Type
Islamorada House
Key Amenities
About this property
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 ...
Property Type
Islamorada Cottage
Key Amenities
About this property
This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers ...
Property Type
Islamorada Condo
Featured review
We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.
Key Amenities
About this property
1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo ...
Property Type
Islamorada Condo
Featured review
Perfect location! Our family had a great week and we will definitely come back. Condo is well furnished, clean and plenty of space. Kitchen is well stocked with essentials. Pool was very refreshing. The ...
$450
avg/night
Key Amenities
About this property
Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy! The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, ...
Property Type
Islamorada House
Featured review
2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights ...
Key Amenities
About this property
Welcome to “At The Sandbar!” This newly built oceanside villa in Islamorada is a wonderful choice for those seeking a serene retreat and an opportunity to immerse themselves in the relaxed nature of the Florida Keys. Situated within the Peaceful Palms community on Windley Key, this three-bedroom, ...
Property Type
Islamorada Villa
Key Amenities
About this property
Popular Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of the world, Islamorada. If you have never experienced summer in the Keys, you might be surprised! ...
Property Type
Islamorada Condo
Distance to beach: 5 miles to Anne's Beach
Key Amenities
About this property
Enjoy the sunrise from the balcony or from the condo through 50' of glass sliding doors. You can also view the sunset from our walkway on bayside. We have a full kitchen, dishwasher to microwave, washer/dryer, even beach towels. We have wifi,cable TV in living area and all bedrooms, master bath ...
Property Type
Islamorada Condo
Featured review
This condo is a great location for families to enjoy the water activities and the many great restaurants in the area. It has an awesome view of the ocean and local bridges. Condo has all the amenities ...
Key Amenities
About this property
Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, pickleball, heated pool, private beach, and dockage for ...
Property Type
Islamorada Condo
Featured review
Excellent stay. Owner is super nice and helpful. Great location, beautiful sunsets. Easy access to both the bay and the ocean. Place was very clean when we arrived. Would stay again.
Distance to beach: 0.5 miles to ANNE'S BEACH
Key Amenities
About this property
Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are ...
Property Type
Islamorada House
Key Amenities
About this property
Escape to paradise and experience the ultimate vacation getaway at our stunning 4-bedroom, 3-bathroom canal home in the heart of Islamorada. Nestled along the crystal-clear waters of the Florida Keys, this exceptional rental offers a perfect blend of comfort, convenience, and natural beauty. Key Features: Spacious ...
Property Type
Islamorada House
Key Amenities
About this property
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 ...
Property Type
Islamorada House
Featured review
We loved Harbor Hideaway for our month long getaway to Islamorada. The home is beautiful with gorgeous sunset views and huge private balconies. The newly renovated bathrooms are fantastic! The outdoor ...
Key Amenities
About this property
Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of ...
Property Type
Islamorada House
Featured review
We stayed here in the “Honu Hale” house in August 2024 during the Florida Lobster Season. The property is ideally laid out & set up for boaters, divers & fisherman. There’s plenty of dockage and a ...
Key Amenities
About this property
Islamorada waterfront gem located on Sandy Cove Basin with total renovations completed in 2024. New pool and spa, new deep water dock. Three en suite king bedrooms. Nicely appointed kitchen. Private gated and fenced yard with ample parking.
Property Type
Islamorada House
Distance to beach: 1 miles to Anne's Beach
Key Amenities
About this property
Secluded Waterfront Apartment with Tiki hut, dock, King bed, 1 Bath, Sleeps 2. Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this ...
Property Type
Islamorada Apartment
Featured review
We stayed two weeks in the beautiful apartment and it was the best vacation ever! Chris is a wonderful host, very friendly and a wealth of information about the area! We will be back next year!
