5 BR | 5 BA | Sleeps 14 | Quick View
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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
We have been renting in the Keys for 22 years, this one topped them all. The grounds are SO secluded and private, makes you feel like your staying in the Jungle. Peacocks, exotic birds, and cool lizards ...
Key Amenities
About this property
Welcome to The Snook House at Tarpon Point!This impressive home is tastefully decorated and features an open floor plan, soaring ceilings, an unimpeded, nearly 180 degrees of breathtaking ocean vistas and four oversized bedrooms, each with their own bathroom.On the main level, you will find the ...
Property Type
Islamorada House
Key Amenities
About this property
MM 81.5. BRAND NEW construction located in the Heart of Islamorada! Coral Cove is a gated, secluded and intimate community of 8 homes on the Florida Bay. Featuring both a private pool in the back, and a community pool on the bay, Coral Cove also features 3.5 bedrooms, 3.5 baths, bay ...
Property Type
Islamorada House
Key Amenities
About this property
Mile Marker 73 – Bayfront observation pier / Boat basin dockage Four bedroom/ four bath home located on a bay front parcel with fantastic protected boat basin dockage. Best of both worlds! Dock multiple boats in your protected boat basin steps from the villa, or walk the grounds the the best sunset ...
Property Type
Islamorada Villa
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 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 bedrooms ...
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 ...
Key Amenities
About this property
Mile Marker 75 – BaysideLarge, 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
4 BR | 3.5 BA | Sleeps 8 | Quick View
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About this property
Explore this sunset heaven from our new bay deck where you can soak in the sun and get lost in our unique sunsets. Listen to the breeze while you sip your wine or go on a sunset cruise while you are in our island. Island Villa 1 is the place to be. It will entice you with all its amenities inside and ...
Property Type
Islamorada Villa
Key Amenities
About this property
Mile Marker 77 – Oceanfront – Lower Matecumbe Key. Seven bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on the private beach, ...
Property Type
Islamorada Estate
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 house has ...
Property Type
Islamorada House
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
Key Amenities
About this property
Wide ocean views from every room in this gated, monthly rented beachfront estate, aptly named ‘Southern Comfort’. Vacation comfortably in this 3 bedroom, 3.5 bath, immaculately kept home. Sprawling grounds on the 1/2 acre estate lead to a heated pool and over 80′ of private beach frontage. ...
Property Type
Islamorada Villa
Key Amenities
About this property
One of the only white sandy beaches in the Fl Keys and 1 mile whole of it!Newly built,state of the art,beautifully done 5 bedroom home, 4 master suites w/ king beds and facing open water! Magnificent indoors and out! Each bathroom is exquisite,very large stone,glass and hand picked tiles. 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
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 ...
4 BR | 3 BA | Sleeps 8 | Quick View
Distance to beach: 5 miles to Founder's
Key Amenities
About this property
MINIMUM STAY: 7 Nights SATURDAY TO SATURDAY The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each home offers two private bedrooms. Between the two homes the bedding is: King, Queen/Queen in Tarpon and Queen, Twin/Twin in Bonefish. ...
Property Type
Islamorada House
We stayed for a month at Blue Water Retreat and had an awesome time with family and friends. The ocean views were magnificent. The pool was a big hit with the kids. We even had our dog with us. Hope to ...
4 BR | 4.5 BA | Sleeps 8 | Quick View
Key Amenities
About this property
‘The Beach House’ at Tarpon Point in Islamorada‘The Beach House’ is a luxurious oceanfront home in a private gated enclave of only 12 houses. This end home offers privacy and beautiful ocean views including of Indian Key Historic State Park. Enjoy morning coffee and a phenomenal ...
Property Type
Islamorada House
This home is stunning from top to bottom and all around. Our family, ranging from 18-75 years of age, found this home to be spacious, comfortable, and well equipped for cooking, relaxing, and having fun ...
3 BR | 3.5 BA | Sleeps 8 | Quick View
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
4 BR | 3 BA | Sleeps 8 | Quick View
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
Arlene was wonderful to work with. The home more than accommodated our mix of four couples. Thanks.
Key Amenities
About this property
Beautiful 5 bedroom pool home with 70 foot of dockage at mile marker 74.5 on the bay side. The first floor is a private apartment with two bedrooms, one has a queen and the other two queens. Has a full kitchen, living room, dining area and full bathroom. The second floor has three bedrooms, two with queens ...
Property Type
Islamorada House
Owner easy to work with, place is nice and clean, is as described. My kids especially enjoyed all of the iguanas that are running around.
4 BR | 4 BA | Sleeps 8 | 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
My wife and I have stayed at Irish Ayes the month of February the last three years. We love it there. This three story home has it all, pool, spa, boat dock even an elevator. The third floor master suite ...
Key Amenities
About this property
Mile Marker 75 – Bayside4 bedroom 3 bathPalm 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
Great house, pool, and area. Lots of attractions and wonderful restaurants. Also, great people to work with.
4 BR | 3 BA | Sleeps 12 | Quick View
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
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. ...
3 BR | 2 BA | Sleeps 6 | Quick View
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 unobstructed 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
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
My husband, our dog, and I, spent the entire month of January in this Fantastic Islamorada pool home with a dock. Tammy, the owner was responsive, helpful, answered all our questions, and emailed to be ...
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
This was a terrific location and home. The house and amenities were excellent. The backyard was the standout for our group with the pool, dock and Tiki area....this felt like a true resort get away. The ...
Key Amenities
About this property
Once you arrive at Keys Tripper Relaxation kicks in. You will experience the Serenity of the Keys while enjoying the Privacy of this Waterfront Home. This 5 Bedroom, 3 Bath Canalfront Home is located in Sought after Port Antigua in Lower Matecumbe which is the South end of Islamorada. The Upstairs Boasts ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Minimum Rental: 7 Days"Little Bay's Cottage" is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area ...
Property Type
Islamorada Cottage
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 5 miles to Founders
Key Amenities
About this property
Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up ...
Property Type
Islamorada Apartment
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
Vacation Rental License 097. Welcome to Anglers Reef, a very special community of vacation homes with UNOBSTRUCTED OCEAN VIEWS FROM EVERY ROOM!We are new to this site so no reviews yet, BUT MANY AT OUR DIRECT SITE (SEE "LINKS" TAB ON THE LEFT) AND 12 YEARS of top reviews ON VRBO PROPERTY ...
Property Type
Islamorada Villa
3 BR | 2 BA | Sleeps 10 | Quick View
Key Amenities
About this property
''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 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 has been remodeled, fully furnished, with a 90 ...
Property Type
Islamorada House
We stayed at Paradise during Feb and March 2022. Outstanding house on a canal 1 block from the Bay. House is well appointed and stocked with everything one needs to enjoy the Keys. Owners were wonderful ...
Key Amenities
About this property
This home is located in the exclusive White Marlin Beach residences. Islamorada is one of the most eco diverse locations in the Florida Keys. The property is fully equipped for all your daily needs. There is 70ft of dock which is available for use while renting. You will also have access to the private ...
Property Type
Islamorada House
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 | 2.5 BA | Sleeps 6 | Quick View
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
We absolutely loved this charming community! It was the perfect place for our family to unwind after the unusual spring and summer! We rented a boat slip and it was an easy - peezy trip to the the sandbars ...
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
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 ...
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 ...
4 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Minimum Rental: 28 nightsPelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. The main floor offers 3 bedrooms and an open concept with ample seating for the entire family. The large balcony overlooks a canal where pelicans are usually seen diving into ...
Property Type
Islamorada House
4 BR | 2.5 BA | Sleeps 9 | 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 9 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
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
Had a wonderful 3 weeks in Islamorada. The unit was perfect location to restaurants, activities etc. we will be returning in 2023
3 BR | 3 BA | Sleeps 6 | Quick View
Distance to beach: 0.5 miles to White Marlin Beach
Key Amenities
About this property
*******Check us out on VRBO No. 2003434******** Please go to ....**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 4 | Quick View
Distance to beach: 5 miles to Anne's Beach
Key Amenities
About this property
Two Queen Beds, sleeps 4 + (1 Bedroom / 1 Murphy Bed)/ 2 Bathrooms, Full LaundryDock your boat up to 26 ft. Free boat trailer parking!The "Nest" is located on beautiful Florida Bay (at Mile Marker 82.3) in Islamorada on upper Matecumbe Key . The Villa is a privately owned condo residence ...
Property Type
Islamorada Condo
If i could have it for a month, i would be there,,, ,dont need any other place. This place is paradise by the bay,,,beautiful sunsets an accomodations. Ill be back.
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
Thank you so much for letting us stay at your condo! It is absolutely gorgeous and you have everything there we needed and more. The location was perfect and our children enjoyed the tennis courts, pool, ...
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, this condo ...
Property Type
Islamorada Condo
Great location with lots of fishing, great restaurants, beautiful sunsets and only 90 minutes to Key West. Highly recommend!
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
August 20 21 was are fourth time staying in this unit. We are already pre-booked for 2022. Easy access for your boat convenient and super clean. Close to awesome restaurants.
4 BR | 3 BA | Sleeps 10 | Quick View
Key Amenities
About this property
MINIMUM STAY: 28 NIGHTS Lyons Landing is an exceptional single family home with pool, dock, boat lift and outdoor living area located in the prestigious neighborhood of Venetian Shores in Islamorada. Everything you need for a spectacular vacation awaits you in this extraordinary home. 3 bedrooms ...
Property Type
Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Minimum Rental: 28 Days "My Paradise" is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The ...
Property Type
Islamorada House
2 BR | 2 BA | Sleeps 8 | Quick View
Key Amenities
About this property
1440 sf - Sleeps 6 (8 with the help of an EZ-Bed electric queen Bed/or large sectional couch with chaise lounge and cuddler). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community beach with beautiful sunsets. Well the ...
Property Type
Islamorada House
We had a fantastic stay at YOLO! The house is beautiful (recently renovated) and very well appointed with linens, towels, kitchenware, etc. and was spotless!There are bikes, kayaks, a ping pong table ...
3 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Minimum Rental: 28 DaysHappy vacationing starts here! The owners call their special getaway “Bay Therapy” for many reasons. It is located in a great neighborhood in Key Largo. It is convenient to the mainland and is the gateway to the Keys. Since purchasing this home the owners have ...
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
3 BR | 2 BA | Sleeps 6 | Quick View
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
My two friends and I agree that in the last 13 years since we have been coming down to Islamorada for our annual fishing trip, this is one of the best places we have stayed in. Instructions were clear, ...
