Islamorada Vacation Rentals, Beach Houses and Condos for Rent

Islamorada Condo 4.4 Star Review

Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and Wifi. The condo boasts some amazing views of the Clear Blue waters of the Atlantic Ocean looking over Sea Oats Beach. Relax on your own private roof top patio and enjoy a beautiful sunrise of the.......read more

Islamorada
3 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 6

Islamorada Private vacation home 4.4 Star Review

Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to enjoy the trade winds and sip your margaritas. The Con.......read more

Islamorada
5 Bedroom(s) - 5 Bath(s)
Private vacation home Rental Sleeps 14

Islamorada Private vacation home

Beautiful tranquil private beach is just the beginning of what awaits you in our completely renovated beach house. Port Antigua is one of the best neighborhoods in Islamorada. Not only does it offer a private beach for members only but also has a private boat ramp right inside the neighborhood. With great fishing access to the bay and open ocean.......read more

Islamorada
4 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Islamorada Private vacation home 5.0 Star Review

Paradise is only a click away. Our 2 BR/2.5 BA conch style townhouse is available for weekly and monthly vacation rentals. Our unit has unobstructed direct ocean views, and overlooks the resort style swimming pool. Dock space is available to rent as well for boats up to 31 ft.
This home is great for a family vacation. There is also a beach.......read more

Islamorada
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Islamorada Private vacation home 5.0 Star Review

Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs. The downstairs apartment has a complete kitchen and living room and separate bedroom. There is a screened in porch of the living room upstairs. The home has awesome dockage that is 70\'. Easy ocean or bay access via Sn.......read more

Islamorada
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Islamorada Private vacation home 4.4 Star Review

With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you\'ll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada\'s Lower Matecumbe Key, near mile marker 76, this traditional one-story Keys bungalow is refurbished. .......read more

Islamorada
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Islamorada Private vacation home 4.8 Star Review

Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in
Lower Matecumbe (South part of Islamorada). This home is the second one in on a point
and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee
maker, toaster, and blender. There are two flat panel TV\'s in the house, as well a.......read more

Islamorada
3 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Islamorada Private vacation home 5.0 Star Review

Luxury in Paradise! Fully remodeled from the floor up, inside and out, all new furnishings in summer of 2022. Your bungalow is one of the original Islamorada bungalows built in the late 60\'s restored to better than new. Come see what the Island Lifestyle in the sportfishing and leisure capital of the world is all about. Castaway Island at Sh.......read more

Islamorada
2 Bedroom(s) - 1 Bath(s)
Private vacation home Rental Sleeps 5

Islamorada Private vacation home 4.8 Star Review

114 Anglers Way
Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many kid friendly features.
Outfitte.......read more

Islamorada
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Islamorada Private vacation home

Our Little Piece of Paradise is a relaxing place to enjoy with family and friends. We look forward to making it your home away from home.
Fully remodeled home on the water, washer and dryer inside the house. TVs in living room and bedrooms. Smart TV and internet are included. Bedrooms include: 1 King Size Bed, 1 Queen Size Bed, 2 Full Size Beds.......read more

Islamorada
3 Bedroom(s) - 1 Bath(s)
Private vacation home Rental Sleeps 8

Islamorada Private vacation home 4.9 Star Review

Beautiful 4-bedroom, 3.5 bath home in Angler\'s Reef. Walk into a brightly decorated, open floorplan, featuring a newly renovated gourmet kitchen including all of the amenities you’ll need for a perfect stay – updated appliances, stone countertops and breakfast bar. A queen bedroom with ensuite bathroom is conveniently located on the first floo.......read more

Islamorada
4 Bedroom(s) - 4 Bath(s)
Private vacation home Rental Sleeps 8

Islamorada Condo 5.0 Star Review

Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo.

This unit located in the complex of Bay Harbour offers a private 50\' boat slip, heated swimming pool, hot tub, club house, fitness center, tennis courts, gas barbequ.......read more

Islamorada
2 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 6

Islamorada Condo 4.9 Star Review

Enjoy the spirit of the Florida Keys in this \'keysey\' furnished condo with everything provided. All you have to do is show up with your shorts and swimsuit. Boat slip is optional. You can be in your boat and heading out to enjoy spectacular fishing, diving, snorkeling, boating, or just cruising and watching the sunset in a flash.

Locate.......read more

Islamorada
2 Bedroom(s) - 3 Bath(s)
Condo Rental Sleeps 4

Islamorada Private vacation home 5.0 Star Review

Our home is in the perfect location in Islamorada....across the street from The Worldwide Sportsman, Morada Bay and Pierre\'s and within walking distance to restaurants, shops and galleries. We are situated on the ocean side of the Overseas Highway at MileMarker 81. There is enough room for a trailered boat in the driveway. Relax on the large scree.......read more

Islamorada
3 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 8

Islamorada Private vacation home 4.9 Star Review

For a relaxing & fun family vacation experience. It is time to change your latitude, attitude & immerse your body & mind in the calming, soothing waters that surround this Florida Keys paradise. So come enjoy Gulf waterfront sunsets in Islamorada, Florida. (OK. I agree, it\'s kind of corny but oh so very true.)

QUICK OVERVIEW:
We offer yo.......read more

Islamorada
4 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 6

Islamorada Private vacation home 4.8 Star Review

Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs makes for a great sunset watching area. The house has .......read more

Islamorada
2 Bedroom(s) - 2 Bath(s)
Private vacation home Rental Sleeps 4

Islamorada Private vacation home

Come stay and watch the sunsets at our beautifully updated Keys townhouse at Executive Bay Club located in Islamorada on the bay. It has 2 bedroom with a loft, 3 full bathrooms and washer/dryer in the unit. It is a private, gated community with a clubhouse, heated swimming pool, a private beach area, a fishing dock and 2 tennis courts. Founders .......read more

Islamorada
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 9

Islamorada Condo 4.6 Star Review

Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 4 people. Stay in touch with family & friends with free wireless int.......read more

Islamorada
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 4

Islamorada Private vacation home 4.5 Star Review

This townhome at Executive Bay will sure make your home away from home! This unit has been completely renovated and decorated beautifully. This
2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a Bayside complex. It is a gated community with 24 h.......read more

Islamorada
2 Bedroom(s) - 3 Bath(s)
Private vacation home Rental Sleeps 6

Islamorada Condo 4.9 Star Review

Beautifully renovated second floor condo at Futura Yacht Club, a private, gated complex with a fabulous marina and pool, just 67 miles south of Miami, at mile marker 88.5 in Islamorada, considered the Sportfishing Capital of the World.
Excellent access to the Ocean through Tavernier Creek or Snake Creek for boating, fishing or snorkeling. Relax.......read more

Islamorada
2 Bedroom(s) - 2 Bath(s)
Condo Rental Sleeps 6