2 BR | 2 BA | Sleeps 4 | Quick View
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
This 5th floor condo did not disappoint. The double balcony offered great views of the bay, and a spiral staircase up to the private roof top was another great place to watch the spectacular sunsets. The ...
2 BR | 2 BA | Sleeps 5 | Quick View
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
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 ...
4 BR | 4 BA | Sleeps 10 | Quick View
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
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
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
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
4 BR | 4.5 BA | Sleeps 8 | Quick View
Distance to beach: 0.5 miles to White Marlin Beach
Key Amenities
About this property
Bring your boat and Jet SkisNestled 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
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 ...
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 0.5 miles to White Marlin Beach
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 DockVilla 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
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 ...
3 BR | 2.5 BA | Sleeps 6 | Quick View
Distance to beach: 2 miles to Anne's Beach State Park
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
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
The condo was lovely! Thoroughly furnished. Updated amenities. Beautiful grounds. On-site staff. Friendly and helpful. Highly recommended
3 BR | 3 BA | Sleeps 6 | Quick View
Distance to beach: 2 miles to Anne's Beach State Park
Key Amenities
About this property
This stunning top floor end unit in Bay Harbour has stunning ocean and harbor views from every room and includes a 50ft. boat slip and a 25,000# lift. BAY HARBOUR ALLOWS 7-DAY RENTALS. The interior design is spectacular. Coffered ceilings in the living area, top of the line Miele and Thermador appliances, ...
Property Type
Islamorada Condo
We have stayed at Bay Harbour before, but this was our first time renting this unit and it was absolutely perfect. The location and water views are wonderful, and the inside of the unit is beautifully decorated. ...
3 BR | 2.5 BA | Sleeps 8 | Quick View
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
5 BR | 5 BA | Sleeps 14 | Quick View
Key Amenities
About this property
Oceanfront Estate on 3.5 PRIVATE Acres in the Heart Of Islamorada. Features include: Private Boat Basin with 100 of feet of dockage for any size boat, private boat ramp and fishing pier. HUGE salt pool and hot tub, 3rd floor private master suite w/ office, master bathroom and private balcony. This huge ...
Property Type
Islamorada House
I can’t express enough how our month in this house was above expectations. It was my retirement party and over the month had friends, family and high school buddies. The house was huge and 5 couples were ...
3 BR | 2 BA | Sleeps 10 | Quick View
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
This was our 4th year on Tollgate and somehow it gets better. Tiff and Bill go above and beyond in accommodating us. The updates look fabulous, love the painting in the dining room. Our dog Max has made ...
3 BR | 2 BA | Sleeps 6 | Quick View
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
Well equipped condo with great sunrises. Our grandson enjoyed fishing from the dock. Convienent to Marathon and Islamorada restaurants. Can't wait to go back A hidden gem
3 BR | 2.5 BA | Sleeps 6 | Quick View
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
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 ...
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
2 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 100 feet to Front door
Key Amenities
About this property
MINIMUM STAY: 30 daysSpacious 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
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
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. ...
3 BR | 2 BA | Sleeps 6 | Quick View
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
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 ...
3 BR | 3 BA | Sleeps 6 | Quick View
Key Amenities
About this property
This home has a private beach entrance directly into the bay and is across from Sea Oats Beach. Enjoy a quick paddle board or kayak trip directly out of the back door. Dock and boat lift avialble for 30+ foot boat. Unmatched views of both the Atlantic Ocean, Gulf ocean or both from every window and ...
Property Type
Islamorada House
4 BR | 2 BA | Sleeps 12 | Quick View
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
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 ...
2 BR | 2 BA | Sleeps 8 | Quick View
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
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 ...
2 BR | 2 BA | Sleeps 4 | Quick View
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
Couldn't have been any better. Perfect location, comfortable beds, great views! The deck right out the door was our favorite place to be. Highly recommend the Nest
3 BR | 2 BA | Sleeps 10 | Quick View
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
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 ...
3 BR | 2 BA | Sleeps 6 | Quick View
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
3 BR | 3 BA | Sleeps 6 | Quick View
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
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 2 miles to Anne's Beach State Park
Key Amenities
About this property
This updated Port Antigua home with 85 ft. of concrete dock is ready for a new family to enjoy. The open floor plan and vaulted ceilings make this house feel so welcoming! French doors with side lights let in the natural light and open to the lanai where you can enjoy your morning coffee or a cocktail ...
Property Type
Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
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
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
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
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 ...
1 BR | 1 BA | Sleeps 4 | Quick View
Distance to beach: 0.3 miles to Anne's Beach
Key Amenities
About this property
Enjoy this modern lagoon front ground level one bedroom condo/apartment with exclusive use of the 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 Ocean side. Dockage available ...
Property Type
Islamorada Condo
After staying in St. Pete Beach for a month, we decided to go south and visit the Florida keys. We found Bill and Carolyn's place on Florida Rentals and decided to give it a go. What a wonderful experience!The ...
6 BR | 4 BA | Sleeps 12 | Quick View
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
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 ...
6 BR | 5 BA | Sleeps 14 | Quick View
Key Amenities
About this property
Welcome to Caribee Beach House!This estate is the perfect mix of old school Islamorada combined with present-day, stylish luxuries. This hidden gem is a special slice of heaven, nestled in downtown Islamorada, boasting with 200 feet of exclusive water frontage, 100’ dock, and fabulous views ...
Property Type
Islamorada House
Key Amenities
About this property
Facing due west this property takes full advantage of the spectacular sunset view over the bay. GreenFlash has a bayside infinity pool and dockage to help you take full advantage of the myriad of water activities available in Islamorada, the 'Sport Fishing Capital of the World.' The two story ...
Property Type
Islamorada House
4 BR | 2 BA | Sleeps 8 | Quick View
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
3 BR | 2 BA | Sleeps 6 | Quick View
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
The condo was very spacious, meticulously clean and well supplied with cooking utensils and supplies. This was probably one of the nicest places we have stayed in the many years we have been going to the ...
2 BR | 2.5 BA | Sleeps 6 | Quick View
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
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 ...
2 BR | 1 BA | Sleeps 5 | Quick View
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
4 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
About this property
This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast. ...
Property Type
Islamorada House
This was a great house! Our whole family enjoyed the stay very much. It was quiet and the layout of the home is perfect for multiple families to stay. The pool area was very nice and the dock is a perfect ...
3 BR | 2 BA | Sleeps 6 | Quick View
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
Perfect location. Everything is close by. Even trips south and even to Key West are no big deal we drove in from North Carolina and we went everywhere. What a great property too our guests who wanted to ...
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
4 BR | 2.5 BA | Sleeps 11 | Quick View
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
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 ...
4 BR | 3 BA | Sleeps 8 | Quick View
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
3 BR | 2.5 BA | Sleeps 6 | Quick View
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
My family and I stayed in this house and everything was absolutely perfect. The house was very clean and the backyard is very spacious for tanning and enjoying the warm sunny weather. I will definitely ...
1 BR | 1 BA | Sleeps 2 | Quick View
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
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!
Key Amenities
About this property
Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated/chilled Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large ...
Property Type
Islamorada House
This was our first family trip to the FL keys and we had the most amazing time! Bridget was so helpful, especially since we booked prior to covid and decided to take our planned trip. She answered all my ...
3 BR | 3.5 BA | Sleeps 6 | Quick View
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
Key Amenities
About this property
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, ...
Property Type
Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends. ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove ...
Property Type
Islamorada Cottage
Key Amenities
About this property
Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking 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 Apartment
