Islamorada Vacation Rentals in the Florida Keys

Islamorada Private vacation home 4.5

Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and Wi-Fi. 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 t.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Islamorada Private vacation home 4.8

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

2 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Islamorada Private vacation home 4.6

Conch & Lobster Homes - Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced conk) is a three bedroom, two bath ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to enjoy the trade winds and sip.......read more

5 Bedroom(s)
5 Bath(s) Sleeps 14

Vacation Home

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, but also has a private boat ramp right inside the neighborhood. With great fishing access to the bay and open ocean just through chan.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Islamorada Private vacation home 4.7

137 LeSerra Lane - 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 on the point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffeemaker, toaster, and blender. There are two flat panel TVs in the house, as wel.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Islamorada Private vacation home 5.0

107 San Remo Drive - 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 porch off the living room upstairs. The home has an awesome dockage that is 70'. Easy ocean or b.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Islamorada Private vacation home 5.0

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

2 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Islamorada Private vacation home 4.4

75691 Overseas Highway (aka Breezy Point Cottage) - 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 tr.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Islamorada Private vacation home 5.0

We are so proud to say our tropical Bungalow now has 65 Straight 5 STAR REVIEWS on VRBO

What sets us apart from "just a vacation rental"? As your hosts, we have spent a lifetime in the hospitality industry. When we chose to purchase, remodel and refurnish the property we set out to achieve 6 main goals. LACBSC, or Location, Amenities, Comfo.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 5

Vacation Home

Islamorada Private vacation home

The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast access to both Ocean & Bay, fuel, bait, and provisions.

Key Features of Salty B:

- The House: Upstairs has Two Bedrooms, with a king-size bed in the Master, and a Full/Twin Bunks (2) in the other guest suite, There i.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 10

Vacation Home

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

3 Bedroom(s)
1 Bath(s) Sleeps 8

Vacation Home

Islamorada Condo 5.0

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.

Located .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 4

Vacation Home

Islamorada Private vacation home 4.6

75130 Overseas Highway - 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. View beautiful sunsets from the screened porch that includes tables and .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Islamorada Private vacation home 4.9

Now available January and part of February - You will see amazing sunsets in our community sandy beach, fish or relax on pier, dip in the heated pool, take a few bikes for ride to Founders Park next door, slide over the water on our kayaks. You can also simply work from home from one of our TWO ready-to-go functional offices

Yes - Last minu.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Islamorada Apartment

Waterfront one bedroom one bathroom located right on overseas highway on Islamorada. The shimmering blue hues of the Atlantic Ocean greet you upon arrival as the fun calls your name. Utilities are included which are water, internet garbage service and electricity. The apartment is fully furnished however it could possibly be rented partially furnis.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

Islamorada Condo

Fabulous 'Sea Breeze 41' is available for rent FURNISHED RENTAL A 30' Boat Slip is available in the CHC Marina. Available 03/20/2023 Experience high-end coastal luxury while staying 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.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Islamorada Private vacation home 4.5

Executive Bay G-5 - Executive Bay is a bayside townhome that is sure to be your home away from home! This unit has been completely renovated and decorated beautifully with two bedrooms and three bathrooms. (1) King Bed, (1) Queen Bed with a bonus room off the Master that has 2 twin beds. Executive Bay Club is a bayside complex. It is a gated commun.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Islamorada Condo 4.7

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

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Islamorada Condo 4.9

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

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Islamorada Condo 4.9

“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much more.

This 2 Bedroom condo at Bay Harbour sleeps 4 adults & two children 6 and under. Easy access to the Gulf or Ocean makes this the perfect home port for any fishing vacation. Bring your own boat or rent from any of.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 4

Vacation Home

Islamorada Private vacation home

Enjoy watching the ospreys and manatees from the dock at this beautiful Port Antigua home on Biscayne Blvd. You have access to a large private sandy beach with zero entry to waist deep water to sit and sun bathe and bring the kids for a splash. 4 beach cruiser bicycles are included for riding around the neighborhood. The dock has a large fish cle.......read more

5 Bedroom(s)
3 Bath(s) Sleeps 10

Vacation Home

Islamorada Villa

Step out the door to your private oceanfront beach with pool and dock at Midnight Runner. The property features two living spaces, downstairs and upstairs. You will enjoy amazing ocean views from the 3rd floor-viewing porch. Enjoy a nice lunch out on the dock, which includes a round concrete picnic table. Midnight Runner has all the amenities for .......read more

5 Bedroom(s)
5 Bath(s) Sleeps 10

Vacation Home

Islamorada Villa 3.0

Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features an exotic wood deck surrounding a custom pool overlooking a private sugar sand beach on the Atlantic Ocean. Newly built-in outdoor shower! This home features an inviting living room with a sliding glass wall and a stunning 180-deg.......read more

4 Bedroom(s)
5 Bath(s) Sleeps 12

Vacation Home

Islamorada Villa 4.9

Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches, shopping, fishing, diving, snorkeling, bike riding, etc.

We provide bikes, kayaks and you can snorkel right from our dock. There are some resident iguanas in our mangroves and with luck you will see a manatee or great wh.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Islamorada Private vacation home 4.9

This Property has a large kitchen and living area open to amazing views of the bay with 4 bedrooms and 3 full baths. You cannot go wrong with the protected boat basin for your boat or jet skis. If snorkeling, swimming or kayaking is your thing, look no further! Either enjoy amazing sunsets in the comfort of the backyard or walk to a fun local h.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Islamorada Private vacation home 4.9

NOTE:
--PLEASE SEND AN INQUIRY TO BE SURE YOUR DATES ARE AVAILABLE.
--DOCKAGE AVAILABLE AT FOUNDERS PARK MARINA RIGHT NEXT DOOR FOR A FEE. NO DOCKAGE AND NO TRAILERS ALLOWED ON PROPERTY. (Condo rules, not ours!!)
The bed configuration is different than the photos but the same beds are all there, as follows: Large bedroom with King bed an.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Islamorada Private vacation home 4.9

Beautiful 4 bedroom, 3 bathroom pool home in lovely White Marlin beach, Islamorada, FL. Home has been completely renovated in the last year. Serene and spacious outdoor area with brand new wooden deck, private pool and private homeowners beach. Two bedrooms/ two baths upstairs. Master Suite with ensuite bathroom. Second Master downstairs with ful.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Islamorada Private vacation home 5.0

This beautiful Venetian Shores pool home with plenty of space to relax and play. Situated on a deep water canal with quick access to the Atlantic Ocean and Florida bay. The property offers lush tropical landscaping, 100 foot dockage. Outdoor covered living area with grill, dining table, and TV. The main floor has 1 master king with shower, and 2 ad.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Islamorada Condo 5.0

Experience all the Florida Keys has to offer in this stunning 2 bed/ 2 ½ bath condominium with an Ocean View, located in Bay Harbour, Islamorada Florida. This quiet gated community allows one to truly escape. Have the trip of a lifetime with Just a couple of friends & BRING YOUR BOAT too (up to 30')!

Amenities include; Large heated/cool p.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 4

Vacation Home

Islamorada Private vacation home 5.0

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 to every place in town.
Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and a half bathrooms, to comfortably accommodate u.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 8

Vacation Home

Islamorada Private vacation home

This unique home gives you the quintessential keys experience. Nestled in a small, quaint gated, private community with ocean views, the house rests on a privately owned cove which empties into the Atlantic Ocean. The cove contains much wildlife including our neighborhood manatees. The community pool overlooks the Ocean affording spectacular view.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Islamorada Private vacation home 4.9

*****New Owners/Listing so you may not see reviews yet for that reason******

***** Please email and I will answer any questions you have!*****


Direct OCEANFRONT home with HEATED POOL, BOAT SLIP, & BEACHES in the desirable Anglers Reef Community. This 4 bedroom, 3 bath home has endless views of the ocean from every room. If you enj.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Islamorada Private vacation home

Welcome to the “Sailfish House” at Tarpon Point!

Soak up the sun and take in the spectacular views at this opulent 4 bedroom, 4 bath home located in the private community of Tarpon Point. Accommodating up to eight adults, this impressive home makes it easy to both entertain and unwind with its open floor plan and incredible panoramic vie.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 8

Vacation Home

Islamorada Private vacation home

San Remo Canalfront - Venetian Shores five bedroom and four bath home with 70 ft. dock just minutes to Snake Creek for instant ocean and bay access. Totally renovated 3800 sq. ft home with all new furnishings. Open concept kitchen, dining room and living room...ready for your extended family with three bedrooms and three bathrooms upstairs, plus tw.......read more

5 Bedroom(s)
4 Bath(s) Sleeps 10

Vacation Home

Islamorada Mobile home 5.0

Islamorada Windley Key affordable . 2 bedroom 2 bath rental. BRAND NEW PARK MODEL. Steps away from the gorgeous turquoise ocean. Bayside is also very close. Beautiful sunsets and sunrises.World class fishing, snorkeling, diving, Ecosystem, Founders Park close by -with all the amenities.
Theater By The Sea, swim with dolphins, mammals close by. .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5

Vacation Home

Islamorada Private vacation home 5.0

Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenient access either bay or ocean with protected dockage. This canal front home has 2 king en-suites upstairs and a relaxing screen porch off of the living room. There is a downstairs apartment with 2 bedrooms and 1 bathroom and small.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home