Islamorada Vacation Rentals in the Florida Keys
Vacation Rentals by Owner in Islamorada .
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Charming 3-Bed, 2-Bath Canal Home in Tavernier, FL, with Private Pool!
Welcome to 128 Tequesta Street, a charming three-bedroom, two-bath waterfront home designed for the perfect Florida Keys vacation. Located on a canal in Plantation Key, the home offers convenient dockage so you can bring your boat and enjoy easy access to the beautiful waters of Florida Bay.
The outdoor space is where this home truly shines. Relax by the pool, gather with friends under the tiki hut, or mix up a drink at the outdoor bar while enjoying the warm Keys breeze. For a little adv.......
9.0 Star Review
3 Bedrooms
- Sleeps 6
Islamorada Vacation Rental
Pets Allowed 
Enjoy stunning views at Bay Harbour C-312, a 3BR condo in picturesque Islamorada.
Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete with tennis courts, pickleball court, weight room, pool, dockage, fish cleaning station, Smart TV's for streaming (no cable) 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 top patio and enjoy a beautiful sunrise of the glow of a famous Florida Keys Sunset.
NOTE: Onsi.......
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef (Unit # 114) 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.
Outfitted with his and her beach cruiser bikes, a pair of paddleboard/kayak crossovers, fishing equipment, pool toys, beach toys, snorkeling gear and much more, you.......
Spacious 5BR home in Islamorada, perfect for 14 guests with ocean views.
Welcome to Alligator Reef Estate, a gated oceanfront property in Islamorada offering two homes on one beautiful waterfront parcel—perfect for larger families or groups looking to enjoy the Florida Keys together while still having their own space.
The estate includes the Conch Home, a 3 bedroom, 2 bathroom home featuring a private fenced heated and chilled pool, outdoor kitchen and bar area, ping pong table, and bicycles for exploring the area. Just in front of it sits the Lobster Home, a co.......
9.2 Star Review
5 Bedrooms
- Sleeps 10
Islamorada Vacation Rental
Pets Allowed
Paradise Retreat
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 channel 5 or channel 2. Lots of amenities and restaurants in the area to list but will provide information at the property. On the second floor there i.......
Enjoy a serene stay at 137 LeSerra Lane, a 3-bedroom canal retreat in Islamorada.
Beautiful designer-appointed oceanside canal home located at Mile Marker 76.5 on Lower Matecumbe Key in Islamorada. Situated as the second home from the point, the property enjoys beautiful ocean views and a peaceful setting while still being close to everything Islamorada has to offer.
The home features a bright, open layout with modern décor and water views from nearly every window. The fully equipped kitchen includes a dishwasher, microwave, coffeemaker, toaster, and blender—everyth.......
Charming 3BR canal home in Islamorada, perfect for your tropical getaway!
Located in the highly desirable Venetian Shores neighborhood, this canal-front home offers quick access to both the Ocean and Florida Bay via Snake Creek — ideal for boating and fishing enthusiasts.
Upstairs features a comfortable two-bedroom, one-bath layout with a screened porch just off the living room, perfect for relaxing after a day on the water.
Downstairs offers a separate one-bedroom, one-bath apartment complete with its own full kitchen and living area — a great setup.......
Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
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 and kayaks available. Lush, tropical landscape adorns this property. .......
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
We are proud to announce- Castaway Island has been named for KW people’s choice awards as a FINALIST for Best Vacation Rental in the Florida Keys. . Being named top three of over 6,000 vacation rentals is the honor of a lifetime. Experience the ultimate tropical getaway in our enchanting bungalow, boasting 82 consecutive 10/10 guest reviews! Our hosts' lifetime in hospitality shines through in the meticulous restoration and thoughtful amenities, ensuring an unparalleled vacation experience........
10.0 Star Review
2 Bedrooms
- Sleeps 5
Islamorada Vacation Rental
Pets Allowed
Pet Friendly 3 Bedroom in Venetian Shores Sleeps 6
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 is one Bathroom upstairs and one downstairs. Downstairs has a queen-sized Murphy bed Enjoy the convenience of a first-floor bathroom, and refrigerator,.......
2 Bedrooms
- Sleeps 6
Islamorada Vacation Rental
Pets Allowed
Beautiful 'Keysey' Condo in Bay Harbour Gated Community 26-0169
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 on Lower Matecumbe this condo is in the city limits of Islamorada....'Sport fishing Capital of the World'! This gated community is beautifully landsc.......
Charming 2-bedroom retreat in Islamorada with stunning open water views.
Enjoy peaceful Keys living at this charming bayside home located at Mile Marker 75 in Lower Matecumbe, the quiet south end of Islamorada. Set in a tranquil neighborhood, this property offers stunning sunset views and a relaxed island atmosphere perfect for a laid-back getaway.
Out back, you'll find a small private beach area surrounded by palm trees, creating a secluded space to unwind and enjoy the bay. The screened porch is the perfect place to take in the colorful evening sunsets, comp.......
9.2 Star Review
2 Bedrooms
- Sleeps 4
Islamorada Vacation Rental
Pets Allowed
Amazing Sandy Beach Sunsets + New Pool + Best Location w/ Park - Bikes & Kayaks
Come and stay in our 3 1/2 bedroom getaway by the scenic bay in breathtaking Islamorada. * Enjoy your community's private white sandy beach, you’ll find sparkling turquoise water and waving palms that make for a genuine island haven. * Immerse yourself in the laid-back island lifestyle in our soothing new heated pool or get active by swimming, kayaking, snorkeling, or pier fishing in our bay. Venture next door to Founders Park for another sandy beach and many fun activities.
Remote Wor.......
Discover the Charm of Island Living
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 internet. The master bedroom has a king size bed with two twin beds in the 2nd bedroom. If your children are small, we have a hi chair and various toy.......
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
“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 the many boat rental companies in the area. If your vacation is more about relaxation, then kick back at one of the near-by beautiful sandy beaches. .......
Fabulous Island Getaway! Easy access to Florida Bay, Private Beach, Elevator
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 cleaning table and steps down into the clean water. Enjoy the breeze and the views from the downstairs covered entertaining area. No neighbors across the.......
5 Bedrooms
- Sleeps 10
Islamorada Vacation Rental
Charming Ocean Front Pool Home with dockage & pool
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 you and your guests to enjoy, at your private home away from it all!
Key Features of Midnight Runner:
- The Main Kitchen (Upstairs) incl.......
10.0 Star Review
5 Bedrooms
- Sleeps 10
Islamorada Vacation Rental
Pets Allowed
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
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-degree ocean view. You'll love to call Turtle Nest "your home away from home".
Key Features of Turtle Nest:
-The kitchen includes all you.......
OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
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 white heron. Pelicans, cormorants and gulls are common. We have a private beach where you can chill out and relax and shady outdoor spaces to enjoy.
.......
Beautiful Bayfront Home with Amazing Sunsets
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 hangout (88 Restaurant) for a homemade Island cocktail. Don t forget to enjoy the "Treehouse" with a card game or just to see a different view :). Bra.......
Keys Paradise with Private Beach and Pool
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!!)
Luxury resort amenities with all the comforts of home!
Gorgeous, spacious condo with modern updates just steps from the crystalline waters of the Florida Bay. Updated kitchen appliances, granite counter tops and fully equipped with all the extras you might imagine mak.......
Beautiful 4/3, pool home in lovely White Marlin beach, Islamorada, FL
Beautiful 4 bedroom, 3 bathroom pool home in lovely White Marlin beach, Islamorada, FL. Serene and spacious outdoor area with brand new wooden deck, private pool and private homeowners beach park. Two bedrooms/ two baths upstairs. Master Suite with ensuite bathroom. Second Master downstairs with full bathroom and den/TV room with queen size pull out couch. Screened in terrace overlooking pool and canal. Flat screen TV's throughout the home. Five minutes access to open bay waters and ocean side........
10.0 Star Review
4 Bedrooms
- Sleeps 8
Islamorada Vacation Rental
Pets Allowed
Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key.
Oceanside Isle - Oceanview Isle is a hidden gem located in a gated condominium complex on Long Key, a quiet location conveniently located between Islamorada and Marathon. This 3/2 end unit has a large private patio with breathtaking views of the ocean, a boat slip that will accommodate boats up to 34' and access to a shared pool. Located on the first floor is an open concept kitchen and living room with unobstructed views of the ocean. Off of the living room is a private balcony with seating and.......
Just a Few Friends - Ocean View and Bring your Boat!
Welcome to your slice of the Florida Keys at the Bay Harbour Condominium Complex in Islamorada. This bright and spacious 2-bedroom, 2.5-bath condo offers the perfect mix of comfort, style, and laid-back island living—ideal for a relaxing getaway with friends or family.
Tucked inside a quiet, gated community, you’ll feel away from it all while still being close to everything that makes the Keys special.
The kitchen is fully equipped with granite countertops and stainless steel appliance.......
Just relisted! Discounts on longer stays ~ Heart of Islamorada ~ Boat Dockage
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 up to 6 adults plus children. The bright living area fully opens up to a private patio, where you'll love to gather by the heated plunge pool with a vi.......
10.0 Star Review
4 Bedrooms
- Sleeps 8
Islamorada Vacation Rental
Pets Allowed
Oceanfront Luxury - Heated Pool, Boat Slip, Beaches & Spectacular Sunrise Views
Wake up to breathtaking Atlantic Ocean sunrises from this stunning direct oceanfront home in the highly sought-after Anglers Reef community in Islamorada. With panoramic water views from nearly every room, this spacious 4-bedroom, 3-bath coastal retreat is the perfect destination for families, couples, boaters, anglers, and anyone seeking the ultimate Florida Keys getaway.
One of the home's standout features is over 800 square feet of oceanfront decking, offering the perfect place to enjo.......
Spacious 5BR San Remo Canalfront iwith hot tub in Islamorada, perfect for 10 guests.
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 two more bedrooms and a full bath downstairs. There is a full kitchen upstairs and kitchenette downstairs, plus laundry on both levels. There is also a .......
5 Bedrooms
- Sleeps 10
Islamorada Vacation Rental
Venetian Shores Pool Home
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 kitchen area. The pool is situated canal side and perfect after a long day of boating. Enjoy grilling your catch in your outdoor canal side kitchen. .......
Spacious 4BR canal home in Islamorada with private heated pool and beach access.
Welcome to your Islamorada escape in the highly sought-after Port Antigua community. This canal-front pool home is set up perfectly for families and groups who want space, dockage, and that true Keys outdoor lifestyle.
Upstairs features 2 bedrooms and 2 bathrooms with a comfortable, open living space designed for relaxing after a day on the water.
Downstairs offers a separate 2 bedroom, 1 bath suite with a kitchenette — ideal for extended family, friends, or multi-generation stay.......
Charming 2-bedroom condo in Islamorada with pool access and ocean views.
Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the community's two tennis courts, along with two bedrooms, both with en-suite bathrooms. All you'll need is your toothbrush and a swimsuit, and you're all set for a fabulous Florida Keys v.......
Charming 2BR condo in Islamorada with pool, hot tub, and beautiful views.
Beacon Reef 404 - Beautiful two-bedroom two baths, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and has amazing views of the Atlantic. Some additional amenities: chairs and tables on balcony, printer, tiki hut by pool, and undercover parking.
If booking more than a year in advance current prices may not re.......
Experience paradise at Oceanfront Maison Matecumbe 303 in beautiful Islamorada!
.Oceanfront Maison #303 - Maison is a premier gated oceanfront complex in the heart of Islamorada. This prime oceanfront three bedroom, two bath flat unit offers an open concept living and dining room with ocean views, an expansive kitchen with an island and bar seating, and large screened in porch overlooking the Atlantic. The master suite offers breathtaking ocean views, a spacious walk-in closet and a bathroom with a shower and jacuzzi tub that will make you feel like royalty. With a state-of.......
Paradise Found - Three Story Beach House w/ private beach, dock and Ocean Views
28 Day Minimum Stay. Please contact us for specific dates of availability.
3 story bayside home with its own beach. Great location. Private residential area, yet close to Everything. Due to unique location, one of only a hand full of homes on the island with views of both the Bay and the Ocean. Three (3) good sized bedrooms and 3 baths. Each bedroom has its own distinct views. The practical - high speed internet, separate work and entertainment areas, smart-tv’s, water and elec .......
WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei
1940s Old Keys Fishing Cottage with dockage available. Large Waterfront property and walking distance to world famous Lorelei Cabana Bar & Restaurant as well as local breweries too ! This 1940s original Keys Fishing Cottage is not fancy, as the ad's photos show, but in great location and has everything you need for a great Islamorada getaway. We can arrange custom days of stay if you are booking a sunset/sandbar/fishing charter with our family. Enjoy the peace and privacy of the large, natural .......
10.0 Star Review
1 Bedrooms
- Sleeps 2
Islamorada Vacation Rental
Pets Allowed
EMAIL WITHIN FOR ALL INQUIRES DIRECT OCEANFRONT JEWEL,Heated Salt Pool,70Ft Doc
PLEASE INQUIRE WITHIN FOR 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 salt water swimming pool
-Brand New (Jan 2019) 70ft deep water dock (very rare for a open water home) with fish cleaning station, and fresh water and lights.
-Brand New White Kitchen with.......
10.0 Star Review
4 Bedrooms
- Sleeps 12
Islamorada Vacation Rental
Pets Allowed
Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of Islamorada. Located within a gated community with 24 hr. security. Includes fully equipped kitchen w/ granite countertops, microwave and s/s appliances; With washer & dryer, plasma TV, electric outdoor grill, cable, and phone. Sleeps up to 8 - oversized master bedroom w/ one king bed, TV, walk-in closet and loft access with 2 twin beds. Second bedroom includes 2 double beds .......