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
$1670
avg/night
Key Amenities
About this property
Magnificent brand new home nestled between Cheeca Lodge Resort and Caribbean Resort with its own private beach offering a unique and luxurious experience for those looking for a private getaway. This 4 bedroom/4.5 bath home services from small to a larger family of 8 . Has it own private salt water pool, ...
Property Type
Islamorada House
Distance to beach: 100 yards to Port Antigua Private Beach
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
Key Amenities
About this property
Sunrise is a spectacular unit within the Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach. Dockage can be obtainable through Islamorada ...
Property Type
Islamorada Condo
Key Amenities
About this property
MM 87.7 . 2 Bedroom & 2 Bath. Rented 28 days minimum Experience the epitome of oceanfront luxury in this exquisite paradise! Delight in fishing the pristine waters of the Keys with the convenience of your own 30ft slip in a secure marina. Unwind in the comfort of your spacious condo that boasts ...
Property Type
Islamorada Condo
Key Amenities
About this property
FALL SALE NOW GOING ON! About $125 a night! Much less than a motel room. The weather is beautiful, and you can now stay in Islamorada for only chump change! 2025 is fully booked till May 1! Popular Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and ...
Property Type
Islamorada Condo
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 ...
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
$15,000-$17,500 Weekly A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just a short 90-minute ...
Property Type
Islamorada House
Key Amenities
About this property
Mile Marker 75 – Bayside Large, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal. The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut, grill and outdoor seating ...
Property Type
Islamorada House
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.
Key Amenities
About this property
Gorgeous updated 2 bedroom, 2 bathroom condo with large modern kitchen in an oceanfront gated building with oceanfront pool, fishing dock, gym, sauna, barbecue grills and so much more, and the best part is YOU'RE IN THE FLORIDA KEYS!
Property Type
Islamorada Condo
Featured review
Great condo, pool, and neighbors. Highly recommend. The pool is heated. Ocean view is great. Community room. Has exercise room and sauna.
Distance to beach: 0.9 miles to Founders Park
Key Amenities
About this property
Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom ...
Property Type
Islamorada Condo
Featured review
Sharon’s condo was absolutely gorgeous! It was super clean upon arrival and had everything we could have needed for our 3 month stay (linens, dishes, pots & pans, cleaning supplies, etc). The interior ...
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 ...
Distance to beach: 5 miles to Founders Park
Key Amenities
About this property
Half Duplex Home Are you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and manatees ...
Property Type
Islamorada House
Featured review
The screened in area and the outdoor space make this rental perfect! We kayaked on the canal, and walked around the neighborhood daily. We watched boats and manatees from the screened in porch. Lee (the ...
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
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
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!
Key Amenities
About this property
Mile Marker 81.6 — Conch Villa Conch Villa, aptly named for the famous large snails that inspired the Keys to be called the ‘Conch Republic,’ is located in the heart of Islamorada. The 3-bedroom villa is rented separately, and is tastefully furnished with modern styles and amenities. ...
Property Type
Islamorada Condo
Key Amenities
About this property
Tea Table Key Private Island Estate and Wedding Venue An extremely rare and stunning private island, accessible by car, Tea Table Key is a gated Caribbean Island located at Mile Marker 79.7 in Islamorada. Jutting into the blue-green waters of the Atlantic Ocean, Tea Table Key features a 2,000′ ...
Property Type
Islamorada House
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
Featured review
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 ...
Key Amenities
About this property
Mile Marker 83 – Oceanfront Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and skiff dock. Relax at the beach or cool down in the beachside pool. The front home ...
Property Type
Islamorada Cottage
Featured review
Just finished a week at Osprey Bay nice house a little too much up and down with all the steps but spacious Need a larger trash can in the kitchen put it next to the wall near toaster Also new pillows ...
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.
Key Amenities
About this property
Fully furnished 2 bedroom 1. 1/2 baths with balcony, heated pool, sauna and fitness room. Also a community room with flat screen and full kitchen, pool and ping pong. Beautiful ocean view from pool and community room. Huge ocean front dock for fishing, snorkeling and kayaking. WiFi , restaurants ...
Property Type
Islamorada Townhome
Key Amenities
About this property
Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat ...
Property Type
Islamorada Estate
Featured review
Absolutely beautiful home..Featured everything we needed to enjoy our vacation..Spacious enough for 14 people. Close to places if we decided to go out n explore..Epic week.!! Thank you
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
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
2 Bed & 2.5 Bath Villa in Anglers Reef with Boat slip.Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious ...
Property Type
Islamorada Villa
Featured review
Beautifully decorated house in the Keys. Very spacious and comfortable. Kitchen was fully stocked. Plenty of linens and extra towels. The community dock has kayaks we used. There are lobsters under ...
Key Amenities
About this property
Traditional coastal cottage styling built in 2017 and the Pool was added in 2020. Large backyard beach and only steps to the turquoise waters of the Atlantic Ocean. Kayak, paddle board, or kite ski from your backyard! Plenty of parking out front and private gated access; fencing around the perimeter. ...
Property Type
Islamorada House
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
Featured review
We had the best time at this house! Giovanna and her husband were wonderful hosts and were on top of everything we needed. The house itself is in a great location close to shops and restaurants. Book the ...
Key Amenities
About this property
Anglers Reef Villa Resort 2 Bedroom and 2.5 Bath Villa, in Anglers Reef with Boat Slip. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch ...
Property Type
Islamorada House
Featured review
Amazing home and location. Great customer support. Would love to return to here again. Islamorada is so beautiful
Distance to beach: 50 yards to White Marlin
Key Amenities
About this property
Located across from White Marlin beach This canal home has protected deepwater dockage , on the most sought-after street, on Gulfview Drive in Islamorada. Enjoy sunset and bay views from White Marlin Beach. Gulfview, known as the 'sugar sand beach', offers 3 bedrooms, 2 bathrooms, dining, ...
Property Type
Islamorada House
Featured review
The home is very comfortable with three bedrooms and a spacious living/dining area. The master bedroom is a bit cozy and lacks a closet, but the two bedrooms that share the Jack-and-Jill bathroom have ...
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
Enjoy breathtaking sunsets on the private beach while staying in this beautifully remodeled corner unit. The unit was completely gutted in 2021 and features 2 bedrooms plus a built out loft and 3 full bathrooms. The unit has a huge master with a king bed plus a bathroom/walk-in closet and ...
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
3 Beds/2 bath townhouse in Islamorada, Florida Keys. Ground Floor features a full kitchen, full bath, living room with large tv, dining room with views of the tennis court, outdoor patio with BBQ and additional dining table. Second Floor features a large full bath, 1 king size bed, 1 queen size bed, 2 ...
Property Type
Islamorada Condo
Key Amenities
About this property
Beautiful area of island on ocean
Property Type
Islamorada Condo
Key Amenities
About this property
Located at Mile Maker 87 Bayside. This gated condo complex offers a large heated pool, club house, Jacuzzi, two tennis court, large Bayside beach. This townhouse (sleeps 8) has just been totally renovated with beautiful tropical furniture, all new kitchen, small garden patio with hammock, living room ...
Property Type
Islamorada House
Featured review
We have never stayed in the Florida Keys before so this was a new adventure that we will definitely do again. The weather was a perfect 80 degrees. Nothing but chill time. We would start the day in the ...
Distance to beach: 4 miles to Founders Park
Key Amenities
About this property
Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air ...
Property Type
Islamorada Condo
Key Amenities
About this property
Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and ...
Property Type
Islamorada House
Featured review
Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt ...
Key Amenities
About this property
Great house! Great location! HOUSE ON CANAL… 34 foot concrete dock with fish cleaning stand, water and electricity. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. We are also ...
Property Type
Islamorada House
Featured review
The house was absolutely beautiful and perfect for bringing your boat. We had four adults and a one year old and the spacious home comfortably and easily accommodated us. Simple and easy access to Snake ...
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
Featured review
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 ...
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
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
PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!! OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated ...
Property Type
Islamorada House
Featured review
Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient. ...
Distance to beach: 2 miles to Founders Park
Key Amenities
About this property
Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condominium (CHC) . Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally decorated in Tropical Modern style. A 30' Boat Slip ...
Property Type
Islamorada Condo
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
Featured review
This home is a literal dream for individuals wanting to enjoy the beautiful outdoors in Islamorada. The beds were super comfortable, and the kitchen was roomy and had everything we needed. The additional ...
Key Amenities
About this property
We are delighted to offer this 2 story, 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! There are a limited number of oceanfront townhomes available at Planation By The Sea! Enjoy the breathtaking views off of all 3 balconies catching the sunrise and sunset. The main living area and upstairs bedroom ...
Property Type
Islamorada Townhome
FAQ
