Key Amenities
About this property
This oceanfront condo is located in Tavernier Key, a community situated along the southern border to Key Largo. The grounds encompass over 60 acres and is situated in a tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise waters of the Florida Keys. From dawn to dusk ...
Property Type
Key Largo Condo
Featured review
Great location. Great unit. Great customer service. Will definitely go again! Everything we needed was there.
Key Amenities
About this property
See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler. You will escape ...
Property Type
Islamorada House
Key Amenities
About this property
Blue Shell is a delightful new canal front vacation home with a pool, just a minute to the ocean and open water and lots of fun amenities! It is also about 10 minutes from both Coco Plum Beach and Sombrero Beach. The dock is 50' and there is parking on the side of the house for truck and trailer. ...
Property Type
Marathon House
Key Amenities
About this property
"SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath attached Villa with neighborhood ocean front beach just down the street! It has a private pool that can be heated or chilled (for a fee), private dock (up to 35' boat), fish cleaning station, bait freezer and 4 new bikes! Additionally, ...
Property Type
Marathon Villa
Featured review
Meredith is prompt and helpful. Everything you could want at the beach or for your boat is provided. This is a big plus if flying in. Hope to return here. Highly recommend!
Key Amenities
About this property
This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms. ...
Property Type
Key West House
Distance to beach: 1 miles to Sombrero Beach
Key Amenities
About this property
Casa Del Sol is a 5 bedroom house with an optional 6th bedroom on the waterfront end of the garage. This is a beautiful little apartment called "The Fish Room", and is available at an additional $950 for the week. Only guests registered at the main house may use this space. Reservations cancelled ...
Property Type
Marathon House
Key Amenities
About this property
This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1. Located just 20 miles away from Key West. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill, Jacuzzi. Full WiFi. TVs in every ...
Property Type
Cudjoe Key House
Featured review
We had a great time, we will definitely be back! Fun in the sun! Close to restaurants and grocery store.
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 ...
Key Amenities
About this property
Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the ...
Property Type
Key West House
Featured review
Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the ...
Distance to beach: 1 miles to In the Key Colony Beach walking distance
Key Amenities
About this property
Hey there, fishing enthusiasts and families! Looking for the perfect Florida Keys getaway? Look no further! My beautiful waterfront home in Key Colony Beach is your dream vacation spot. Imagine this: You wake up to stunning sunrises over the open water, have coffee on the wrap-around porch, and ...
Property Type
Key Colony Beach Villa
Featured review
Stayed with a group of friends from around the country. The house was very clean and well provisioned Kitchen, bedrooms, bathrooms, outdoor cooking area. Met the host and hostess, who were very pleasant. ...
Key Amenities
About this property
This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented ...
Property Type
Key West House
$488
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
Mile Marker 75 – Bayside 4 bedroom 3 bath Palm Cottage South, is a charming, modern home directly on the canal with a heated, private pool, dockage, and access to the Port Antigua community sandy beach. Dockage for 24′ boat max on the lift pictured. Elevated for great breezes and ...
Property Type
Islamorada Villa
Featured review
Great house, pool, and area. Lots of attractions and wonderful restaurants. Also, great people to work with.
Distance to beach: 3 miles to Sombrero Beach
Key Amenities
About this property
The Cozy Conch is ideally located, just walking distance from the historic 7 mile bridge. Take a bike ride along Overseas Highway, enjoy the nearby beaches or have a cozy night by the fire pit at the dockside lounge and BBQ area or the hammock park. The lower levels offers a full-size kitchen, living/dining ...
Property Type
Marathon House
Featured review
This new rental is beautifully decorated with new furnishings. The upper deck overlooks the heated pool and just steps away from the elevated deck overlooking the Atlantic ocean. Appliances are new and ...
Key Amenities
About this property
Blue Turtle Villa at The Tides of Vaca Cut (Unit #4), is a brand new 5 bedroom 4 bath home with a private pool, boat slip, all the toys for the perfect vacation ~ paddle boards, kayak, giant Jenga, giant connect four, ping pong and more! Perfectly situated on the water with stunning views, sunrise and ...
Property Type
Marathon House
Featured review
The home is absolutely beautiful and in a great location, beautiful views and has all the amenities needed for a great family vacation!
Key Amenities
About this property
Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional ...
Property Type
Marathon House
Featured review
I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would ...
Distance to beach: 3 miles to Sombrero Beach
Key Amenities
About this property
Welcome to DragonFly Lite our home in Marathon, FL in the heart of the beautiful Florida Keys, the house has 2 bedrooms a Queen in the master and 2 twins in the guest room, one bathroom + our outdoor shower, all the towels you will need for the pool or beach (please leave the sand outside). It’s ...
Property Type
Marathon House
Featured review
Though Dragonfly Lite would be a marvelous place to vacation anytime, it proved especially so in a global pandemic. We had everything we needed right there on property. The pool is pristine, the home was ...
Key Amenities
About this property
Our waterfront, single-family home, affectionately named “Turtle Cove”, offers 3 bedrooms, 2 baths, and an 80 ft seawall with quick ocean access! This tastefully furnished Keys home is located on a quiet side street in a residential neighborhood on the Atlantic side of the Island, just 5 houses ...
Property Type
Marathon House
Featured review
House was clean, pool area great, any small issues we encountered dealt with promptly. Close to everything needed.
Distance to beach: 4 miles to Sombrero Beach
Key Amenities
About this property
Come stay with us! Why? Because we have 64 FIVE STAR reviews!! The highest number of reviews for ALL properties listed here on this site!!! Welcome to the luxurious “Yellowtail” Villa, where luxury meets the Gulf of Mexico! The only problem with this vacation rental is you won't ...
Property Type
Marathon Villa
Featured review
I'm not sure where to start with the compliments!!! This villa has a Gorgeous waterfront view and 4 stories of amenities to enjoy. The villa is decorated with an awesome island vibe, super clean; the kitchen ...
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
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
Tropically furnished condominium with amazing views of the Gulf of Mexico, located at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. Enjoy your morning coffee, watching the boats go out. Relax, ...
Property Type
Islamorada Condo
Featured review
Fantastic host. fantastic location, fatastic accomodations! Looking forward to returning in 2022. Thank you Susan
Distance to beach: 175 yards to K Building
$209
avg/night
Key Amenities
About this property
This beautiful end unit is nestled in the most charming area of the best condominium complex in Key Largo. As you walk up to the front of the unit, you will be pleased by the inviting seating area and the paved walkway. It is close to the community beach and near the inlet. Your end unit allows you the ...
Property Type
Key Largo Condo
Key Amenities
About this property
Beautiful house in Big Pine Key, Fl on the water. Bring your boat and have it in the water in the back of the house. Comes with everything needed for your amazing stay. There is an ice maker for your use as well. Also you are only 30 miles away from the world famous Key West.
Property Type
Big Pine Key House
Key Amenities
About this property
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most ...
Property Type
Key Largo Villa
Featured review
We have been spending time here for 11 years now. Love our summer stay at your cozy home. Thank you for letting us make great memories here
Key Amenities
About this property
Our home is a unique tropical paradise in Key Largo. Our kids named it Manatee Corner for the friendly visiting Manatees. It’s a three-story duplex, open concept with a wrap around balcony. We are blessed with a canal that opens to the Atlantic Ocean providing direct access to the most incredible ...
Property Type
Key Largo House
Featured review
I have been renting in Key Largo for 10 years The unit I had rented became unavailable. This unit had all items needed and if there was something else I need the owner took care of it right away. The ...
Key Amenities
About this property
The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views. The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge. Fishing and diving just steps outside your door. Then at night, Key West is ...
Property Type
Key West House
Featured review
My family booked Seaview Estates for our 25th Anniversary trip! We rented both houses so we had the property to ourselves. Upon arrival, Carol met us at the gate and began our tour of the property. The ...
Key Amenities
About this property
This 3 bedroom, 2.5 bath single-family modern home is great for entertaining! Enjoy the outdoor area with a pool and a separate hot tub or catch a game of pool on the main floor. This home is located on the 63rd Street canal and being ocean-side, it's just a quick trip out to sea where you'll ...
Property Type
Marathon House
Featured review
The house is absolutely beautiful! It was very comfortable for our family of 4 plus a dog. The kitchen included everything we were looking for. The pool was a great benefit! We used it everyday. The ...
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
The Blue Turtle Villa, located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool with a heater and a chiller, and all the amenities you would ...
Property Type
Key Colony Beach Villa
Distance to beach: 0.5 miles to Key Colony Cabana Club Beach
Key Amenities
About this property
Beautiful 2-story half duplex home on wide canal with boat slip. Sleeps 10 comfortably. 4 bedrooms, bathrooms and lower-level family room with mini kitchen make this a great place for multiple families to have private space or gather together. Plenty of parking for boat trailer and multiple vehicles, ...
Property Type
Key Colony Beach House
Featured review
Rare find of 4 full baths and 4 real bedrooms (not a daybed stuck in a sunroom like some rentals market as a bedroom). House comes with everything you need - beach towels, coffee maker, toaster, blender, ...
Key Amenities
About this property
VACA-22-238 BRAND NEW BUILD! 3- bedrooms with king beds and full size bathrooms, and 1/2 bath for guests. Large common area living room and open kitchen. Located on canal three houses from the ocean, with great open water views. Pool with sitting area under the house. Our home offers a 60' ...
Property Type
Marathon House
Featured review
This Florida rental was exceptional. We had booked this property two years prior to our vacation date and were using this as a family vacation. Unfortunately, a week before our vacation my Father passed ...
Key Amenities
About this property
Fly, drive or skipper your vessel to this newly remodeled, waterfront home in Key Colony Beach. Key Colony Beach is one of the most desired neighborhoods in the Florida Keys. We welcome you to stay at our three bedroom, 2 bathroom home that is fully equipped for your vacation enjoyment. Weekly, monthly ...
Property Type
Key Colony Beach House
Featured review
Attractive coastal vibe in this comfortable retreat.We stayed there for five weeks and enjoyed every minute,especially the large screened porch overlooking the canal.Also we especially enjoyed the updated ...
$386
avg/night
Key Amenities
About this property
This Condo comes with 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
Lower Matecumbe Key Condo
Featured review
We enjoyed the quiet. Room was spotless. Complex has comfortable adult mature feel. Easy drive to many restraunts
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: 1 feet to on property or at Founders Park
Key Amenities
About this property
Beautiful new home on Florida Bay with sandy beach, spacious pool, beautiful views, and sunsets every night. Three Private Suites are offered to accommodate up to 12 guests. Each suite can be rented individually or combined. I would be happy to discuss your needs and answer any questions you may have. ...
Property Type
Islamorada House
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
Villa, 4 Bed + Convertible bed(s), 3.5 Baths (Sleeps 6 - 10), Free Secure WiFi! An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction ...
Property Type
Key Largo Villa
Featured review
This was a great location to celebrate my husband's 60th birthday with our adult children and significant others. The condo was conveniently located in Key Largo and the grounds were well maintained and ...
Key Amenities
About this property
We have a lovely oceanside cottage in Marathon Key, Florida, close to everything with hidden amenities. The cottage has a large yard and plenty of room to park boats, RVs, and wave runners. This modernized cottage is for you if you all need a great place to stay. This quaint and cozy home offers good ...
Property Type
Marathon Cottage
Key Amenities
About this property
WELCOME TO THE KEYS! Mega tropical oasis with 2 HOUSES! No you are not dreaming. Yes there are 2 houses connected together totaling 5 beds, 3 full bathrooms, 2 outdoor showers , 2 six person Hottub’s and 2 kitchens. Along with kayaks, beach bikes, volley ball, bocci ball, fire pit, corn hole and ...
Property Type
Marathon Villa
Distance to beach: 0.4 miles to Higgs Beach
Key Amenities
About this property
Tiki Tango - Your Key West Oasis in the Coveted Casa Marina District! Welcome to Tiki Tango, a grand 2-bedroom, 2-bathroom home that blends island ambiance with modern luxury. Located in the coveted Casa Marina District of Key West, this vacation rental promises a memorable stay with its private pool, ...
Property Type
Key West House
Key Amenities
About this property
The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...
Property Type
Islamorada Apartment
Featured review
We’ve been coming to the Keys for 20 years and this place takes the win. Jerry and Lisa are so friendly and make you feel very welcome and comfortable. The apartment has everything you need including ...
Distance to beach: 1 miles to Sombrero Beach
Key Amenities
About this property
Embark on an idyllic getaway to our spacious 4-bedroom, 3-bathroom vacation villa nestled in Marathon, the heart of the Florida Keys. Escape to Stay Anchored, where tranquility meets luxury. Boasting a prime location on a spacious canal, our retreat features a private heated and chilled pool, inviting ...
Property Type
Marathon House
Featured review
We really enjoyed our stay there, the home was decorated nicely and was fully stocked with all the essentials needed for a hone away from home stay. We had ample enough rooms for the four couples to stay ...
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: 0.1 miles to On site
Key Amenities
About this property
BEST SUNSETS in the Keys, Key Colony Point unit #15, Ocean Beach Front, 2 bedroom, 2 bath ensuite, newly remodeled Condo with new furniture. COMPLEX: KEY COLONY POINT UNIT #15 Perfect get away for a week or a month. BEACH is 30 feet from our balcony. 150 feet to pool with hot tub. Great fishing ...
Property Type
Marathon Condo
Featured review
Had a great time at this condo at Key Colony Point. Everything in this unit was new and nicely appointed. It was relaxing sitting by the pool and fishing on the pier was a nice added activity. Would ...
Key Amenities
About this property
We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you ...
Property Type
Islamorada Condo
Featured review
Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.
Key Amenities
About this property
Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer. Dos ...
Property Type
Key West House
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: 23 miles to Marathon
Key Amenities
About this property
Charming house on a canal with all amenities like home. Bring your own boat and park it on the dock for the duration of your vacation. Convenient located 25 miles before Key West. Nice restaurants and groceries shopping 10 minutes from the house Marathon is only 30 minutes away. A short boat ride ...
Property Type
Little Torch Key House
Featured review
This canal front home is close enough to everything to be convenient, yet far enough away from everything to be private and secluded. Easy access to the Atlantic and Gulf for boating, close to picnic ...
Key Amenities
About this property
Family House in Big Pine Key, Fl on the water. Bring your Boat and have easy access to the most beautiful waters of the Keys. Boat dock on the back of the house, and house comes with everything, it will make you feel at home. Welcome to your Ultimate Luxury Island Escape! This beautiful waterfront ...
Property Type
Big Pine Key House
