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 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 condo

Bay Harbour A304

Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - Bay Harbour A304

Beautiful 3 bedroom and 2.5 luxury condo located at mile marker 74.5 bayside. This condo is nicely decorated and very spacious for you and your family. The unit has a great screened in porch off the living room. The complex has 2 tennis courts, wei ....

3 Bedroom(s) 3 Bath(s) Condo
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 house

La Jolla Resort

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 ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 8
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 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 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

Angler's Reef Resort & Villas

4 Bedroom House In Angler's Reef, Includes 31' Boat Slip

Beautiful 4 bedroom, 3.5 bath home for rent in Angler's Reef. This house has a bedroom with a queen bed and an ensuite bathroom downstairs. There is also a half-bath downstairs. The gourmet kitchen has marble counter tops, a wine cooler and a bar. Th ....

4 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 8
Islamorada, FL

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Islamorada townhome

A8 Islamorada

Florida Keys' Jewel - Executive Bay Club

An ample 1,400 sq ft. town home in the heart of Islamorada. Two bedrooms and one bathroom upstairs. One bedroom has two queen beds and cable television. Second bedroom is set up with one queen bed and cable television. Sofabed and bathroom downstairs ....

2 Bedroom(s) 2 Bath(s) Townhome
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 townhome

Executive Bay - A7

**Winter Promo** Modern Executive Bay Club Condo with 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

PARADISEPOINT

OceanfrontPeninsula Pool Dock water3sides 7nite min 6ppl max

MINIMUM stay 7 nights, MAXIMUM occupancy 6 people, rental pattern saturday to Saturday, SORY NO PETS COMMENTS AT HOMEAWAY #341722, VRBO #311382 A SLICE OF PARADISE. This is it...Search no More -you have found the needle in the hay stack. You are in ....

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

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Islamorada house

La Jolla Resort

3 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 ....

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

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Islamorada house

83003 Old Highway

Beautiful Oceanfront Oasis with Pool - 83003 Old Hwy.

Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in ....

4 Bedroom(s) 3 Bath(s) Vacation Rental
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 mobile home

Vacation Home

Top of the line Mobile home unit located at Islamorada resort. Full restaurant

Beautiful Mobile home fully loaded with all ameneties. breathtaking views just steps away from the Gulf of Mexico and the Atlantic Ocean. Unit will sleep 5 people comfortably. Queen bed in the rear bedroom plus two pull out beds in the main hall. Ev ....

1 Bedroom(s) 1 Bath(s) Mobile Home - Sleeps 5
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

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 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 cottage

Paradise Cottage

RELAX in your PRIVATE Oceanfront Cottage!

1/1 cottage with breathtaking oceanfront views. Sleeps four comfortably. Private bedroom with queen bed. Living room has two full size futons. New kitchen with all stainless steel appliances. Very cozy and great views to enjoy in your dream vac ....

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

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 house

Anglers Reef

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

This lovely oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500' of ....

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

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Islamorada house

Vacation Home

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 ....

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

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Islamorada house

Little Palm Caribbean Home

Little Palm Home - Enjoy Boat Harbor & Fishing Pier

Guests enjoy the beautiful Caribbean décor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone flooring. Open living and dining area all add to your tropical experience. Comfortable lounging chairs create a seamless trans ....

1 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 4
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

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 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 condo

Vacation Home

Bay Harbour - Developer Unit Every Upgrade Possible!!***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 Luxuriously appointed condo located at Mile Marker 75 on t ....

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

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Islamorada condo

Bay Harbour Condominium #204

??Luxury 3 Bedroom Condo -Amazing Views, Sunrise, Pool/Hot Tub, Kayak/Gym/Bikes

Located in Islamorada, Florida, this beautiful condominium is located in Lower Matecumbe Key, and feels like old Florida. Our home is a 3 bedroom, 2.5 bath and sleeps 6 people comfortably. The 3 bedroom unit includes an extra large living area and ba ....

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