Islamorada Florida Vacation Rentals, Hotels & Resorts

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Rentals in Islamorada, FL

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Search hundreds of Beachfront Vacation Rentals in Islamorada, Florida Keys

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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Islamorada, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Islamorada townhome

Executive Bay - T2

**Winter Promo** Family Friendly Executive Bay Townhome with Beach & Pool

We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions App ....

3 Bedroom(s) 2 Bath(s) Townhome
Islamorada, FL

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Islamorada house

Vacation Home

NEW RENTAL! Venetian Shores waterfront dream with pool and plenty of dockage.

This Venetian Shores pool home has 4,209 sq. ft. of living to spread out and enjoy your Keys vacation. This includes 2 living levels, with 2 bedrooms/1 bath on the first level and 3 bedrooms/2 baths on the second floor. Beautiful living room, update ....

5 Bedroom(s) 3 Bath(s) Vacation Rental
Islamorada, FL

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Islamorada apartment

Bay Harbour D114

Stunning 3 Bedroom Condo with Oceanviews Located in Lower Matecumbe - Bay Harbour D114

Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does have Wi-Fi. The Bay Harbour Complex comes complete with two tennis courts, weight room, ....

3 Bedroom(s) 3 Bath(s) Apartment
Islamorada, FL

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Islamorada villa

Islamorada Paradise

Islamorada Home In Paradise - NO HURRICANE DAMAGE TO HOUSE OR COMMUNITY

NO HURRICANE DAMAGE TO HOUSE OR COMMUNITY!!! This beautiful villa, 106 Anglers Reef, is fully licensed by the Village of Islamorada for Vacation Rentals, license # VR-224. It is located in the exclusive oceanfront gated community of Angler's Reef ....

2 Bedroom(s) 3 Bath(s) Villa - Sleeps 6
Islamorada, FL

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Islamorada condo

Vacation Home

2 BDR Penthouse-Breathtaking view-Designer Furnished-***7 Day Minimum Rental***

***NOTWITHSTANDING ANYTHING IN THE RATES PAGE THE MINIMUM RENTAL IS 7 DAYS***IF YOU SEARCH LESS THAN 7 DAYS MY PROPERTY DOES NOT APPEAR***THE MINIMUM RENTAL PERIOD IS 7 DAYS*** Bay Harbour www.bayinthekeyscom Luxuriously appointed condo located at M ....

2 Bedroom(s) 3 Bath(s) Condo
Islamorada, FL

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Islamorada house

The White Marlin Beach 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 th ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 5
Islamorada, FL

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Islamorada house

Angler's Reef

Angler's Reef Resort Villa 136, a 2 Bedroom with Balcony Ocean View

The Angler's Reef Resort's villa 136 will provide your group with more than enough space to ensure their comfort and privacy. Complimentary covered parking will keep your mind at ease knowing your vehicle is well-protected. Just outside the living ar ....

3 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL

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Islamorada house

113 Sunset Drive

Charming Beach Front Home in Lower Matecumbe - 113 Sunset Dr.

Near the house is the small Anne's Beach. There are nature trails, board walks to small lunch and BBQ areas, private sandy areas hidden in the mangroves and parking. The home is also near Robbie's Marina (where they feed the Tarpon), Bud n' Mary's Ma ....

4 Bedroom(s) 3 Bath(s) Vacation Rental
Islamorada, FL

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Islamorada house

132 Atlantic Lane

Beautifully Renovated 2 Bedroom Oceanfront Home - 132 Columbus

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 pr ....

2 Bedroom(s) 2 Bath(s) Vacation Rental
Islamorada, FL

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Islamorada house

151 Anglers Way

Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach

This magnificent home with amazing direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Home also overlooks the community pool. Anglers Ree ....

2 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL

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Islamorada villa

The Island Dog Villa

The World Famous Island Dog Villa of Islamorada in the Florida Keys

Perfect location for your Florida Keys Vacation Newly remodeled Villa in the beautiful Florida Keys. The Villa offers 2 Bedrooms, Boat Storage, Private Community Boat Ramp with Private Ocean Channel Access, Heated Pool, Private Community, LED Flat ....

2 Bedroom(s) 1 Bath(s) Villa - Sleeps 5
Islamorada, FL

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Islamorada house

ENTIRE BEACH HOUSE TWO IN ONE

W AVAILABLE 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 ****************************************** https://my.matterport.com/show/?m=Cc7CWBsnjpA&brand=0 Enter ....

4 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 12
Islamorada, FL

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Islamorada house

102 Columbus

Charming 2 Bedroom Canalfront Home in Islamorada - 102 Columbus Dr.

Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer ....

2 Bedroom(s) 2 Bath(s) Vacation Rental
Islamorada, FL

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Islamorada townhome

Windy Cove #1

Wonderful 3 Bedroom Oceanfront Townhome with Pool - Windy Cove #1

Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units ....

3 Bedroom(s) 2 Bath(s) Townhome
Islamorada, FL

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Islamorada condo

Summer Sea Condominium

Kick Back In Islamorada!

Remodeled 2 Bedroom unit includes air conditioning, private balcony, cable TV, DVD player, full kitchen with cooking utensils, pots & pans, silverware, plates, glasses, microwave, coffee maker, dishwasher, iron, ironing board, blow dryer and refriger ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 6
Islamorada, FL

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Islamorada house

4 BR Villa w/ pool Canal front-- Great access to the Ocean in Islamorada, Florida

4 BR Villa w/ pool Canal front-- Great access to the Ocean in Islamorada, Florida

MM 91. Situated on a clean, clear canal with deep water access to either the bay or ocean via Tavernier Creek! Enjoy your island time in this bright and breezy hideaway ... Two bedrooms/Two baths upstairs along with open living, dining and kitchen. T ....

4 Bedroom(s) 3 Bath(s) Vacation Rental
Islamorada, FL

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Islamorada house

141 Ocean Lane

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 resident ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Islamorada, FL

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Islamorada house

Islamorada's Tropical Paradise

Tropical Paradise in Venetian Shores. Luxury Heated Pool / Spa, 4 Bikes & Kayak

Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled in 2014/15 so everything is tasteful, high quality, spotless and NEW!! HI SPEED WIFI and NetFlix is INCLUDED! A brand new luxury he ....

3 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL

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Islamorada condo

Executive Bay Club

Executive Bay Club unit V4 Islamorada,FL

SERVICE ANIMALS are OK, otherwise NO PETS ALLOWED 30 Day Minimum Stays 2 Bedroom, 1.5 Bathroom townhome located in Islamorada, FL. Driving distance is only 90 minutes from Miami International Airport. Centrally located within the complex to tennis ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 10
Islamorada, FL

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Islamorada house

454 Palm Drive LLC

Beautiful 3/3 Islamorada Waterfront Home

Our home is in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the southernmost island in Islamorada, at exactly Mile Marker 74, on the bayside. Our home is a 3/3, and can comfortably sleep six, ....

3 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL

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Islamorada house

Beach Dream House

Beach Dream House, relax and enjoy the clear waters of Islamorada FL

Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun rising over the Atlantic Ocean and superb views from every room in the house: 360 degrees of glass and a wraparound balcony . Pool and ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL

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Islamorada townhome

Executive Bay G5

Tastefully Renovated Townhome with Great Community Amenities - Executive Bay G5

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 ....

2 Bedroom(s) 3 Bath(s) Townhome
Islamorada, FL

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Islamorada apartment

122 Valencia Dr

Unique Venetian Shores Home with 3 Bedrooms and Dockage - 122 Valencia Dr.

Charming canalfront home in prestigous Venetian Shores. A simple yet lovely, ground level 3 bedroom, 2 bath home with direct access to ocean and bay via Snake Creek. With 70 feet of dockage, a fish cleaning station, gas grill, and great outside patio ....

3 Bedroom(s) 2 Bath(s) Apartment
Islamorada, FL

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Islamorada townhome

Executive Bay - Q4

**Winter Promo** Fully Renovated Executive Bay Club Condo with Modern Décor, Pool & Beach

We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions App ....

3 Bedroom(s) 2 Bath(s) Townhome
Islamorada, FL

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Islamorada house

Vacation Home

ISLAMORADA PARADISE! Welcome to your private heaven on earth!

Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous panoramic ocean vi ....

3 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 6
Islamorada, FL

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Islamorada house

Alligator Reef - Conch Home

Alligator Reef - Conch Home

Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean bre ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Islamorada, FL

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Islamorada estate

Vacation Home

Luxury Florida Keys Estate

Ocean Front, Lush Gardens, Private Beach, Deep-Water Dockage, Brand new Pool with Spa. This luxurious and newly renovated home is situated on the very desirable Lower Matecumbe Beach in Islamorada. This gated home offers supreme peace and privacy ov ....

3 Bedroom(s) 3 Bath(s) Large Estate Home - Sleeps 6
Islamorada, FL

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Islamorada house

Murphy’s Paradise

Fantastic Beachfront Home Private Gated 1 Acre Estate

Book now for your family vacation of a lifetime. Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of The Florida Keys. “The sport fishing capital of the world.� So beautiful that the Netflix series Bloodli ....

5 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 12
Islamorada, FL

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Islamorada house boat

Vacation Home

Enjoy the lifestyle of the Key in Islamorada. Monthly rent have 32.5%discount

Very nice and clean Houseboat in the beautiful Islamorada in the 82 Mile The boat have one bedroom with a queen bed and a TV, another bedroom with a queen mattress, complete bathroom , kitchen, living room with TV also and a sofa bed queen, dining r ....

1 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 4
Islamorada, FL

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Islamorada house

Vacation Home

Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream

Welcome to Paradise! This fabulous Old Florida Style home with Tommy Bahama décor throughout is a Fisherman & Water Enthusiast's Dream! ***Ask about reduced seasonal rates Sept thru Nov! Located in a beautiful, quiet cul-de-sac, on a deep water ca ....

3 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 10
Islamorada, FL

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Islamorada Florida Keys Vacation Rentals, Hotels & Resorts

Plan your Islamorada Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Islamorada, Florida Keys.

Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Islamorada and the Florida Keys.

Spend quality time with your family and friends at cheap low rates you can afford, all while near the beach, nightlife, entertainment and a wide variety of beach activities. If you visit Key West in October, make sure to book your Vacation Rental here for Fantasy Fest. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.

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