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Islamorada Vacation Rentals in the Florida Keys

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Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Islamorada, Florida.

We have partnered with a major provider for Vacation Rentals by Owner, directly through Florida Vacation Rental Homes. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida.


Islamorada House

Oceanfront Angler's Reef #148 - Islamorada House

Oceanfront Angler's Reef #148 - Stunning 2 Bedroom Key West Style Home. Beautiful ocean views from your island-style villa at Angler's Reef. Relax on the front porch overlooking the Atlantic and just steps from the pool. The winding streets and the lush landscaping give Angler's a quaint Key West vibe. The unit is comprised of two upper level spacious bedrooms and two and a half baths. One king master en suite and one ....

2 Bedrooms 3 Baths - Sleeps 6
Islamorada, FL

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Islamorada House

Florida Keys Bungalow #1 - Islamorada House

Islamorada Escape - Bungalow #1 - Cozy, clean, tropical oasis!. The Keys are open! This hidden gem is your piece of paradise waiting! It is tucked away in a small, quiet community of 6 other bungalows at Mile Marker 76, less than a mile south of Robbie's world famous marina. This bungalow features 1 king sized and 1 queen sized bedroom, 1 full bathroom with brand new shower and fixtures, a full kitchen with sta....

2 Bedrooms 1 Baths - Sleeps 4
Islamorada, FL

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Islamorada House

CONCH HOUSE - Islamorada House

CONCH HOUSE WITH ACCESS TO MARINA, FISHING PIER, AND POOL. Guests stay in original Conch House. Comfortable lounging chairs, outdoor deck and BBQ. Two bedrooms, two baths, great room and four flat screen TV's. You are on the same property as our Caribbean Resort with access to one-of-a-kind tropical garden beach-entry pool, Boat harbor and fishing pier. Home includes washer-dryer, BBQ gas grill, wirele....

2 Bedrooms 2 Baths - Sleeps 6
Islamorada, FL

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Islamorada House

Sunset Dr - Islamorada House

Unique Oceanfront Keys Home on a Private Beach**Last minute discounts available!. ###We offer last minute discounts! If your dates are in less than 30 days, please ask us for a discount. Spectacular Oceanfront home on a private beach, ocean side near Anne's Beach on mile marker 74. Ideal for kite surfing enthusiasts, taking a stroll on the beach or just relaxing and enjoying the breathtaking view of the Atlantic Ocean. ....

4 Bedrooms 3 Baths - Sleeps 8
Islamorada, FL

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Islamorada House

Alligator Reef - Conch Home - Islamorada House

Alligator Reef - Conch Home. 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....

3 Bedrooms 3 Baths - Sleeps 8
Islamorada, FL

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Islamorada House

Hawksbill Cottage - Islamorada House

Hawksbill Cottage - Tranquil 1 Bedroom Cottage. The Hawksbill Cottage is a very unique quiet space comprised of a one bedroom and one bath ground level home. Lush landscaping gives the cottage a very tranquil feel. If you have family members or guests visiting you have the option of adding on the upper level of Hawksbill referred to as the Treehouse with their own private entrance. The upper lev....

1 Bedrooms 1 Baths - Sleeps 2
Islamorada, FL

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Islamorada House

Lodge Sol at La Jolla Resort - Islamorada House

3 Bedroom Private Oceanfront House - Sol. Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overlooks the bay, with unparalleled privacy and nearly 2 acres of tropical trees, private boat docks and some of the best unobstructed sunset views the keys have to offer. Complete with fire pits, private outdoor seating, chaise loung....

4 Bedrooms 3 Baths - Sleeps 8
Islamorada, FL

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Islamorada House

The White Marlin Beach House - Islamorada House

RATES REDUCED!! White Marlin Beach House, Islamorada . Contact owner for rates and availability at (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' Enjoy deep blue water or back country fishing. Dive, snorkel, and swim on a clear, white, sandy beach (rare in the Keys!). Walk/jog among beautiful waterfront homes. Sip wine while gazing at glorious sunsets whil....

2 Bedrooms 2 Baths - Sleeps 5
Islamorada, FL

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Islamorada House

Kara Pan - Islamorada House

Kara Pan - Beautiful 5 Bedroom Oceanfront Estate. Islamorada's Exquisite Oceanfront Estate Home... KaraPan 1. This discreet Key West style home is situated on a four acre parcel surrounded by lush landscaping and a natural white sand beach dotted with palm trees. When entering the winding driveway you will be intrigued with anticipation of the captivating views that are only seconds away. Kara Pan....

5 Bedrooms 6 Baths - Sleeps 12
Islamorada, FL

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Islamorada Condo

Executive Bay Club R-6 - Islamorada Condo

Executive Bay Club R-6 - Wonderful 2 Bedroom Condo in Great Location. Wonderful condo in Islamorada's gated bayfront complex. Executive Bay Club is comprised of town homes with bayfront beach access, tennis, clubhouse, fishing pier and swimming pool. Fabulous location right next to Founder's Park that offers an olympic size pool, splash pad and play ground for the kids, quiet beach, tennis and sporting fields. The t....

2 Bedrooms 2 Baths - Sleeps 6
Islamorada, FL

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Islamorada Apartment

Maison Matecumbe #307 - Islamorada Apartment

Beautiful Maison #307. Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centrally located right in the heart of Islamorada within walking and biking distance to many restaurants, cafes, shopping, marinas and Islamorada's Art District. The unit offers an open lower level living room with kitchen and guest bedroom and full bath. Bea....

3 Bedrooms 3 Baths - Sleeps 6
Islamorada, FL

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Islamorada House

Islamorada Beach Duplex - Islamorada House

W AVAIL BOAT Separate & Together Duplex 70' Concrete Dock w Private BEACH. ****************************************** Copy and paste the link below into a browser so you can see the 3D video tour of my amazing property ****************************************** property is currently receiving a pool installation to be completed by end of September Enter the above 3D VIRTUAL TOUR Link into a browser. This listing is f....

4 Bedrooms 2 Baths - Sleeps 12
Islamorada, FL

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Islamorada House

Venetian Shores Pool Home - Islamorada House

Venetian Shores Pool Home -Newly Renovated Four Bedroom Canalfront 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 canalfront 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 ....

4 Bedrooms 3 Baths - Sleeps 7
Islamorada, FL

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Islamorada House

Exquisite Oceanfront - Islamorada House

Exquisite Oceanfront - Gorgeous 5 Bedroom Oceanfront Estate. Luxury and tranquility await you at this elegant Islamorada oceanfront estate pool home. Drive through the gated entry to your own paradise. Spectacular views of the Florida Keys waters. Luxurious beachfront living with comfortable accommodations for family and guests. The main house offers 4 bedrooms and 4 bathrooms with a powder room adjacent to ....

5 Bedrooms 6 Baths - Sleeps 10
Islamorada, FL

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Islamorada House

Tarpon Bay Castaway - Islamorada House

Brand New / Totally Renovated Luxurious Home with POOL. ***POOL Build in July 2019 with amazing landscaping for privacy*** PLEASE inquire directly with us about the specific rate based on the length of stay (SHORTER or LONGER)! Located in Islamorada the premier Key of the Florida Keys, which is known as the Sports Fishing Capital of the world. Islamorada is actually made up of five Keys and this beaut....

3 Bedrooms 2 Baths - Sleeps 8
Islamorada, FL

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Islamorada Townhome

Anglers Reef - Islamorada Townhome

Anglers Reef 116 - 2 BR - BEYOND BEACHY. All NEW Anglers Reef Villa 116, a modern beach retreat offering relaxation at its finest. Our Villa is perfect for families or couples seeking to make the best of their Florida Keys vacation. Enjoy a fresh cup of coffee each morning on the Patio or and take in the fresh seaside air. Cook meals with ease in the open and fully stocked kitchen. Angler....

3 Bedrooms 3 Baths - Sleeps 6
Islamorada, FL

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Islamorada House

194 Airstream Lane - Islamorada House

Stunning 3 Bedroom Bayfront Home - 194 Airstream Lane. The most spectacular bay views from this stunning Islamorada home. This newly remodeled home offers 3 bedrooms and 2 baths upstairs with a beautiful kitchen and spacious living room overlooking the bay. Downstairs there is one bedroom and one bathroom, with another living room for guests. This perfect vacation home offers kayaks, bikes, a summer ki....

3 Bedrooms 3 Baths - Sleeps 6
Islamorada, FL

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Islamorada House

132 Atlantic Lane - Islamorada House

Beautifully Renovated 2 Bedroom Oceanfront Home - 132 Atlantic Ln.. Looking for your next Home away from Home? You can not go wrong in this recently renovated 2 bedroom and 2 bath canal home in Lower Matecumbe at the 76 Mile Marker. This home has everything you need for your next get-away in Islamorada. Only one property away from the Atlantic Ocean, you can literally watch the sun rise from the dining room tabl....

2 Bedrooms 2 Baths - Sleeps 6
Islamorada, FL

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Islamorada House

75731 Overseas Highway - Islamorada House

Gorgeous Key West Style 4 Bedroom Oceanfront Pool Home - 75731 Overseas Hwy.. You are overcome with tranquility and relaxation as you pass through the gates of this oceanfront estate.You are greeted with ocean breezes and luscious landscaping making you feel like you've entered you're own little oasis. This French Caribbean home has a large infinity pool, a private oceanfront beach, incredible porches to sit and watch the su....

4 Bedrooms 4 Baths - Sleeps 10
Islamorada, FL

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Islamorada House

113 Sunset Drive - Islamorada House

Charming Beach Front Home in Lower Matecumbe - 113 Sunset Dr.. Come and stay in this adorable "beachy back yard" home located on the crystal clear Atlantic Ocean! This home truly has amazing water frontage. The home has plenty of room for your whole family to relax having 2 bedrooms upstairs and 2 bedrooms downstairs! Near the house is the small Anne's Beach. There are nature trails, board walks to small lu....

4 Bedrooms 3 Baths - Sleeps 8
Islamorada, FL

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Islamorada House

Treehouse Cottage - Islamorada House

Treehouse Cottage - Cozy Oceanfront Studio. The Treehouse studio is the most coziest second story home overlooking the lush landscaping and nestled in with the palm trees. The home is situated on 2 acres with beautiful landscaping and prime ocean frontage. Relax by the pool, enjoy the sunrise and gorgeous blue Atlantic waters. There is a boat basin for protected dockage. Paddle boards, kayak....

1 Bedrooms 1 Baths - Sleeps 2
Islamorada, FL

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Islamorada House

Vacation Rental - Islamorada House

Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.. Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and private dock, close to the best restaurants, and sight seeing. Peaceful, quiet and relaxing! Just what is needed to take your mind off of business and a great place to spend the winter months in turquoise, warm waters. Fish, read a bo....

3 Bedrooms 3 Baths - Sleeps 6
Islamorada, FL

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Islamorada House

Bayside Retreat - Islamorada House

Bayside Retreat - Adorable 3 Bedroom Bayfront Home with Dockage. Completely renovated bayfront duplex home... this bayfront home consists of 3 bedrooms and 3 bathrooms in Lower Matecumbe. With charming island decor and the open concept living room, kitchen and dining area, the home is light and airy. The screened in balcony directly off the kitchen enables you to enjoy outdoor dining with beautiful bay views. Th....

3 Bedrooms 3 Baths - Sleeps 6
Islamorada, FL

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Islamorada House

Lodge Bahia at La Jolla Resort - Islamorada House

4 Bedroom Private Oceanfront House - Bahia. Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overlooks the bay, with unparalleled privacy and nearly 2 acres of tropical trees, private boat docks and some of the best unobstructed sunset views the keys have to offer. Complete with fire pits, private outdoor seating, chaise loung....

4 Bedrooms 2 Baths - Sleeps 8
Islamorada, FL

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Islamorada House

141 Ocean Lane - Islamorada House

3 Bedroom Home with Ocean Views and Canal Dockage - 141 Ocean Ln.. "The Beach Fixes Everything".That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the three-bedroom, three-bathroom house offers a 270 degree vi....

3 Bedrooms 3 Baths - Sleeps 6
Islamorada, FL

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Islamorada Condo

Sandy Pointe - Islamorada Condo

Sandy Pointe - Serene Sunsets from Your 2 Bedroom Villa. Serene Sunsets from your villa! Sandy Pointe is located in prestigious Port Antigua on Lower Matecumbe. This condo is a comfortable 2 bedroom 1.5 bath, open dining and living room with bar seating to separate the kitchen. Step outside and relax on your private white natural sandy beach looking out into the bay. This beach is known for it's unbeliev....

2 Bedrooms 2 Baths - Sleeps 4
Islamorada, FL

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Islamorada House

Villa Grande - Islamorada House

Villa Grande - Spacious 5 Bedroom Bayfront Home. Spacious Bayfront Family Home! Expansive Gulf views, open deck, walk in beach and dockage. This home is set up with two separate entrances. The South side of the home is comprised of one master king en suite, upstairs, with open living room, dining area, kitchen and full bath downstairs. The North side of the home has four bedrooms and two baths, o....

5 Bedrooms 4 Baths - Sleeps 10
Islamorada, FL

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