Islamorada Florida Vacation Rentals, Hotels & Resorts

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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

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 condo

Ocean Harbour M43

**Winter Promo** Luxurious Ocean View Condo w/Heated Pool & Jacuzzi

*** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large windows at this modern and luxurious oceanfront condo at mile marker 87. Accommodation - Sleeps 4 Master Bedroom: - King Size Bed - Nig ....

2 Bedroom(s) 2 Bath(s) Condo
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 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 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 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

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

Tarpon Bay Castaway

Brand New / Totally Renovated Luxurious Home New To Rental Market.

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 mad ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 9
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

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

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

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 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 estate

Lo Key Estates

BEAUTIFUL 5 BDR HOUSE

*VIEW VIDEO* https://www.youtube.com/watch?v=LQFOSPnfS4Y&feature=youtu.be Lo-Key Estate is truly a luxury Keys home situated on a private 400’ waterfront peninsula with the use of a tropical swimming pool w/waterfall and hot tub(shared w/guest ho ....

5 Bedroom(s) 6 Bath(s) Large Estate Home - Sleeps 10
Islamorada, FL

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Islamorada house

91 West Plaza del Lago

Tastefully Renovated 3 Bedroom Canal Front in Port Antigua - 91 West Plaza Del Lago

Awesome renovated home in Port Antigua. The upstairs has 3 bedroooms and 2 baths. The kitchen has granite counter tops, stainless steel appliances, along with a serving window if you are out on the balcony. The downstairs has a great tv room with ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
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 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 townhome

Windy Cove #3

Great 3 Bedroom Oceanfront Town Home with Pool - Windy Cove #3

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 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 house

4BR Canal front home with splash pool, patios, boat slip & more!

4BR Canal front home with splash pool, patios, boat slip & more!

4BR Canal front home with splash pool, patios, boat slip & more! Seas the day is a fun, 4 bedroom house set on Lower Matecumbe Key in the beautiful Islamorada. On visiting the property, you'll first notice that it's just 3 small lots away from the At ....

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

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Islamorada house

Dream Escape at Anglers Reef in Islamorada

Dream Escape at Anglers Reef in Islamorada

2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard terrace with barbe ....

3 Bedroom(s) 3 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 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 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

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

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

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 house

75731 Overseas Highway

Gorgeous Key West Style 4 Bedroom Oceanfront Pool Home - 75731 Overseas Hwy.

Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and oth ....

4 Bedroom(s) 4 Bath(s) Vacation Rental
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

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 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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