Islamorada Vacation Rentals

(66 rentals)
Palms #309 - Exceptional condo with panoramic views of the Atlantic Ocean.

$82

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen ...

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Property Type

Islamorada Condo

"Great place to relax"
Reviewed August 3, 2019

Condo is in great location and in nice condition Everything was as was promised Loved the pool and walking in the ocean Great dining just walking distance Only thing I would ask is better kitchen ...

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'A little Piece of Paradise" Islamorada, Fl. On the water! 3/2, 90 Ft of dock

$200

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!'' Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. There is a 1/1 guest suite attached which does have its own seperate and private access with full kitchen and bath. Entire house has been remodeled, fully furnished, with a 90 ft Dock. Bring ...

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Property Type

Islamorada House

"Can't wait to get back"
Reviewed July 2, 2020

Absolutely a wonderful place to stay. Easy access to Gulf or Atlantic with plenty of room for 3 boats. Great location for all the Florida Keys has to offer. Was always a pleasure to talk to Bill and he ...

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Bay Harbor 116D

3 BR | 1 BA | Sleeps 6 | Quick View

$414

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This Condo comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks.

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Property Type

Islamorada Condo

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Dream Home in the Keys

5 BR | 3 BA | Sleeps 12 | Quick View

1

$357

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large bedrooms ...

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Property Type

Islamorada House

"Large luxury waterfront home"
Reviewed August 26, 2018

We had the most exceptional time at this home. It’s spacious with enough rooms for everyone. The house was clean and well put together. The linens in every room are luxurious and majority of the beds ...

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My Paradise - Oceanfront beach house with protected dockage.

$262

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

Minimum Rental: 28 Days "My Paradise" is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida ...

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Property Type

Islamorada House

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Oceanviews

2 BR | 1 BA | Sleeps 4 | Quick View

$100

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Mai Paradise Beautiful and breathtaking ocean views in Lower Matecumbe Key in Islamorada. Private Beach Master Bedroom with King size bed Second bedroom with full size bed Inflatable full size bed available One full bath with bath tub Living room with sofa, sofa chair, accent chair, tv, with ...

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Property Type

Islamorada Apartment

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Pelican Landing - Waterfront Home With Dock and Access to Community Beach

$263

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

Minimum Rental: 1 MonthPelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. The main floor offers 3 bedrooms and an open concept with ample seating for the entire family. The large balcony overlooks a canal where pelicans are usually seen diving into ...

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Property Type

Islamorada House

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Southern Diversion Islamorada

5 BR | 3.5 BA | Sleeps 17 | Quick View

$1214

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat ...

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Property Type

Islamorada Estate

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PALMS #317

1 BR | 1 BA | Sleeps 4 | Quick View

$63

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

MINIMUM RENTAL: 1 Month The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful sunshine. ...

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Property Type

Islamorada Condo

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Waterfront Retreat

1 BR | 1 BA | Sleeps 2 | Quick View

$77

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Pet Friendly
  • Rentals by Owner

About this property

Eclectic yet spacious waterfront retreat with beautiful views of Florida Bay. One queen bedroom with bath, huge living area, dining room and open kitchen. Situated on a private acre on the bay with sandy beach, boat ramp, jetty, tiki bar and sunsets nightly. Very private and serene setting to enjoy ...

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Property Type

Islamorada Apartment

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PALMS #313

2 BR | 2 BA | Sleeps 4 | Quick View

$87

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Spectacular oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Alligator Reef Lighthouse is easily visible from your master suite or the balcony and you'll be able to watch cruise ships as they pass by the reef and adventure seekers as they ...

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Property Type

Islamorada Condo

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West Plaza del Lago - Gorgeous Waterfront Home with Boat Lift and Beach Access!

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$133

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...

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Property Type

Islamorada House

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Little Bay Cottage- Gated Bayfront Property Shared with 2 Other Rental Units

$393

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Minimum Rental: 7 Days"Little Bay's Cottage" is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area ...

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Property Type

Islamorada Cottage

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Bay Therapy - 3 Bedroom Waterfront Home with Hot Tub and Boat Dock

$160

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 28 DaysHappy vacationing starts here! The owners call their special getaway “Bay Therapy” for many reasons. It is located in a great neighborhood in Key Largo. It is convenient to the mainland and is the gateway to the Keys. Since purchasing this home the owners have ...

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Property Type

Islamorada House

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Martin Family Fish Camp - Private Bayfront Peninsula with 2 Cottages & Dockage

4 BR | 3 BA | Sleeps 12 | Quick View

1

Distance to beach: 5 miles to Founder's

$543

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

MINIMUM STAY: 7 Nights The Martin Family Fish Camp is located on a private peninsula and offers two cottages named Bonefish and Tarpon. Each cottage offers two private bedrooms. Between the two cottages there is sleeping for 10 in beds plus an additional 2 on the sleeper sofa for an occasional ...

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Property Type

Islamorada Cottage

"Awesome"
Reviewed July 11, 2019

We stayed for a month at Blue Water Retreat and had an awesome time with family and friends. The ocean views were magnificent. The pool was a big hit with the kids. We even had our dog with us. Hope to ...

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Antigua Place - Charming vacation home located in Port Antigua.

$187

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

MINIMUM RENTAL 1 MONTH: Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal. You’ll ...

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Property Type

Islamorada House

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The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip

$429

per night

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Key Amenities

  • Air Conditioning
  • Private Pool
  • Rentals by Owner

About this property

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs ...

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Property Type

Islamorada House

"Great place!"
Reviewed April 22, 2019

Arlene was wonderful to work with. The home more than accommodated our mix of four couples. Thanks.

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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$171

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Oceanfront
  • Rentals by Owner

About this property

The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...

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Property Type

Islamorada Apartment

"Beautiful Oasis"
Reviewed July 23, 2020

This was our second stay here and we are already talking about our next trip! Jerry & Lisa are wonderful hosts and we love the privacy of staying here rather than a resort. I HIGHLY recommend their rental ...

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...

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Property Type

Islamorada Condo

"Wonderful location and hosts."
Reviewed January 10, 2019

This home was perfect for our family of five. Spacious bedrooms, living area and bathrooms. We also had use of the storage unit for our fishing gear and coolers. The pier is breathtaking. Our thoughtful ...

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Beacon Reef #522 - Oceanfront 5th floor (top floor) condo at Beacon Reef.

$147

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy ...

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Property Type

Islamorada Condo

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Beacon Reef #310 - Beautiful condo with lovely views of the ocean.

$113

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days"Beacon Reef 310" is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your ...

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Property Type

Islamorada Condo

"PERFECT VACATION GETAWAY!"
Reviewed June 9, 2019

This beautiful condo was beautifully decorated for the island appeal. Very clean, and conveniently located. Everything we needed for a PERFECT vacation. Pool and Grounds were also immaculate, with a ...

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Sunshine Place - Ground Level Unit with Ocean Views.

$180

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

Minimum Rental: 7 Days"Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people ...

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Property Type

Islamorada House

"Wonderful!"
Reviewed April 23, 2019

Beautiful view; lots of privacy; an exceptional experience! The home was immaculate and had a “well-supplied” kitchen. We genuinely enjoyed our stay, We loved getting up in the morning and having ...

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Beacon Reef #222 - Gorgeous condo with panoramic views of the Atlantic Ocean.

$147

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

Minimum Rental: 28 Days"Beacon Reef 222" is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. ...

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Property Type

Islamorada Condo

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Canal Front Villa with a Tiki Hut, Kayaks, Bikes, Pool, Neighborhood Beach!

$321

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

"Dockside Retreat" ~ rent one side or both! Warm and inviting coastal decor, this 4/3 villa is the perfect vacation home! This beautifully decorated Villa is truly a relaxing retreat and a vacation home that offers you everything you need for a fun filled Keys vacation, including an oceanfront ...

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Property Type

Islamorada House

"Awesome house!!!"
Reviewed January 27, 2020

We recently stayed in the dockside retreat and loved it. We traveled to Marathon with my wife, kids, and mother in law and all thoroughly enjoyed our stay. The house was clean, new, and had everything we ...

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PALMS #404

2 BR | 2 BA | Sleeps 6 | Quick View

$77

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Minimum Rental 1 month. This is an exceptional 2 bedroom and 2 bath condo located in one of the most popular Islamorada condo complexes - The Palms of Islamorada. The balcony is large enough to dine or recline and offers fabulous open water views. While sipping coffee in the morning you can watch ...

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Property Type

Islamorada Condo

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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks & more

3 BR | 2 BA | Sleeps 6 | Quick View

6

Distance to beach: 0.5 miles to White Marlin Beach

$457

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Rentals by Owner

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6Villa Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three bedrooms, two bath, private home totally renovated and remodeled, new furniture ...

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Property Type

Islamorada House

"Best vacation ever!"
Reviewed July 3, 2019

We stayed at Villa Marlin for 2 weeks this June and it was wonderful! The house is equipped with everything you could possibly need for the perfect vacation. The ice machine and bait freezer were a real ...

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Palms #407 - Beautiful condo with panoramic views of the Atlantic Ocean.

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

Minimum Rental: 28 Days"The Palms #407" is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. ...

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Property Type

Islamorada Condo

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Villa Riolo - Updated home and perfect for your next holiday in Islamorada

$122

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

Minimum Rental: 28 Days"Villa Riolo" is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity ...

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Property Type

Islamorada House

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Gorgeous waterfront home

3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada ...

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Property Type

Islamorada House

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Apartment with beach access.

1 BR | 1 BA | Sleeps 2 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

The apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape. ...

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Property Type

Islamorada Apartment

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Sunrise on Sunset

3 BR | 3 BA | Sleeps 12 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

MINIMUM STAY: 28 DAYS “Sunrise on Sunset” is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level area. This spacious 3BR/3BA single family home offers many ...

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Property Type

Islamorada House

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1 bd with sleeping loft, Atlantic Ocean

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 2 miles to Founder's Park

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

#41 Windley Key RV Park84961 Old Overseas Highway Islamorada, Florida Keys 33036 1 bedroom + sleeping loft. $2900 per month includes rent, all utilities, taxes and fees. Available 7/1/2020. Minimum rental period is one month, longer term preferred. No pets. No smoking. Community jetty plus ...

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Property Type

Islamorada Mobile Home

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Island Conch Cottage

2 BR | 1.5 BA | Sleeps 4 | Quick View

5

Distance to beach: 0.5 miles to Anne Beach

$125

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

Island Conch Cottage A quaint ground level conch style cottage located at the end of a private street in a very quiet setting. Cottage and grounds have privacy fence and gate. The grounds are displayed as a sand beach setting. This property has 60’ of canal frontage located on an extra wide canal ...

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Property Type

Islamorada House

"Great Location for multiple outdoor activities"
Reviewed November 20, 2019

This has all that you need for 4 people. Great boat dock for those that have one or will rent a boat. Super easy access to ocean and the same for gulf side. You can fish any wind because of the location. ...

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BEACON REEF #503

2 BR | 2 BA | Sleeps 4 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

MINIMUM STAY: 28 DAYS FIRST TIME ON RENTAL MARKET. This exquisite condo has been TOTALLY remodeled and updated from top to bottom. This is a 5th floor unit with ocean views from the balcony and master bedroom suite. The furnishings are all brand new. There are three TV's - one to suit everyone's ...

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Property Type

Islamorada Condo

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Flamingo Cottage - Adorable 2 bedroom, 2 bath cozy cottage with pool.

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 DaysFlamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like feeling ...

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Property Type

Islamorada House

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Hidden gem 2/2 villa, stunning waterfront views, boat ramp & free dockage!

2 BR | 2 BA | Sleeps 4 | Quick View

10

Distance to beach: 5 miles to Anne's Beach

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Rentals by Owner

About this property

2 Queen Beds, sleeps 4 + (1 Bedroom / 1 Murphy Bed)/ 2 BathroomsDock your boat up to 26 ft.The "Nest" is located bay-side at Mile Marker 82.3 in beautiful Islamorada. The Villa is a privately owned condo residence (one of only 7 units) which is wonderfully maintained and a true hidden ...

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Property Type

Islamorada Condo

"More than a gem"
Reviewed January 2, 2020

The home was exactly as described but better. Every detail was attended to including instructions on how to use everything right down to the remote controls. Exceptional use of space with comfortable ...

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Waterfront Paradise on Canal W/New Pool

$355

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy!The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, ...

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Property Type

Islamorada House

"Waterfront Paradise"
Reviewed July 26, 2020

This was a terrific location and home. The house and amenities were excellent. The backyard was the standout for our group with the pool, dock and Tiki area....this felt like a true resort get away. The ...

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Waterfront Elegance: Dock/Heated Pool/Spa - Ultimate Vacation Rental

4 BR | 4 BA | Sleeps 8 | Quick View

2

Distance to beach: 2 miles to Founders Park

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

This tropical waterfront beauty has it all...heated pool, spa, dock, boat lift and custom elevator. It is beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal, it has direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one ...

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Property Type

Islamorada House

"Islamorada Paradise"
Reviewed March 6, 2019

My wife and I have stayed at Irish Ayes the month of February the last three years. We love it there. This three story home has it all, pool, spa, boat dock even an elevator. The third floor master suite ...

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Bay Harbor 110C​

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Anne's Beach State Park

$257

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

This Condo sleeps 4 and comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key, Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks. Newly refurnished and refurbished, this condo ...

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Property Type

Islamorada Condo

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Blue Heaven Coastal Cottage

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach

$217

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

House, 3 Bedrooms, 2 Baths, (Sleeps 4-6)Spacious ground level home that will be easy on your legs--NO stairs to climb! The home is fully equipped with linens for the queen, queen, and 2 double beds. The master bedroom has its own bath. A separate media room with a flat screen TV as well as a large ...

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Property Type

Islamorada House

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Greenflash

4 BR | 4 BA | Sleeps 8 | Quick View

$600

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Facing due west this property takes full advantage of the spectacular sunset view over the bay. GreenFlash has a bayside infinity pool and dockage to help you take full advantage of the myriad of water activities available in Islamorada, the 'Sport Fishing Capital of the World.' The two story house has ...

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Property Type

Islamorada House

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Ocean Harbor M31

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Founder's Park

$250

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This Condo is located on Plantation Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Ocean Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a fourth floor end unit location make it easy to access your stunning ...

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Property Type

Islamorada Condo

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Brand New Waterfront Home with Pool and Dock

$450

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast. ...

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Property Type

Islamorada House

"SPECTACULAR WATERFRONT PROPERTY !"
Reviewed September 9, 2019

HOUSE – Brand new house (built in late 2018) with an excellent open floor layout and high ceilings, clearly built thinking of: large family + vacation. It has two very large common areas (living/family ...

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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

$269

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo ...

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Property Type

Islamorada Condo

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DIRECT OCEANFRONT POOL HOME W/ Deep Water dock, Huge Heated Pool INQUIRE WITHIN!

$400

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

PLEASE INQUIRE WITHIN FOR ALL 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 ...

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Property Type

Islamorada House

"Truly the best stay we have had in the Keys in over 15 years. Gorgeous views and awesome location!!"
Reviewed January 31, 2019

We have been renting in the Keys since 2005 and have booked many homes from Key Largo to Marathon and this one surpassed them all. The views are amazing, pool was big and warm, beds comfortable and the ...

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BEACON REEF 306 - ISCBEAC306

2 BR | 2 BA | Sleeps 4 | Quick View

$100

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen

About this property

Minimum Rental: 1 Month Enjoy a relaxing stay here in the Keys at this immaculate and charming two bedroom and two bath condo. While the owners attend to their other property "up north" you can relish all the delightful amenities of their condo. This unit is beautifully appointed and ...

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Property Type

Islamorada Condo

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Waterfront Paradise with Free Dockage - Contact us to price your stay!!

1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 12 miles to Founders Park

$100

per night

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Key Amenities

  • Air Conditioning
  • Rentals by Owner

About this property

Secluded Waterfront Studio with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this listing. ...

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Property Type

Islamorada Studio

"Little piece of paradise!"
Reviewed July 26, 2020

We stayed two weeks in the beautiful apartment and it was the best vacation ever! Chris is a wonderful host, very friendly and a wealth of information about the area! We will be back next year!

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Island Living with Gulf Views

2 BR | 2 BA | Sleeps 4 | Quick View

$121

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Tropically furnished, privately owned condominium at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. Enjoy your morning coffee watching the boats go out. Relax with a amazing sunset and a glass ...

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Property Type

Islamorada Condo

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Little Bay - Entire Compound Islamorada FL 33036

$1179

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

MINIMUM RENTAL: 7 NIGHTS This is a lush tropical setting in a gated compound located directly on Florida Bay. Protected dockage in the "Little Bay" will keep your 30' boat (or smaller) safe. There’s a “sunning” area with lounge chairs on the peninsula so you can capture ...

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Property Type

Islamorada Estate

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FISH WHISTLE - ISH137BAYV

4 BR | 3 BA | Sleeps 10 | Quick View

$500

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

MINIMUM STAY: 28 DAYS Fish Whistle is an amazing privately owned estate located directly on Snake Creek in Islamorada. It offers spectacular views and easy access to the Atlantic Ocean or Florida Bay for either sport fishing or diving/snorkeling activities. This home comfortably sleeps 8 people in ...

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Property Type

Islamorada House

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Islamorada Vacation Rentals

Islamorada Weather

 | 

7524°  6217°
JANUARY
Ocean 7423°
7624°  6217°
FEBRUARY
Ocean 7423°
7826°  6518°
MARCH
Ocean 7624°
8228°  7021°
APRIL
Ocean 7926°
8529°  7423°
MAY
Ocean 8127°
8731°  7725°
JUNE
Ocean 8329°
8932°  7926°
JULY
Ocean 8530°
8932°  7826°
AUGUST
Ocean 8730°
8731°  7725°
SEPTEMBER
Ocean 8530°
8429°  7423°
OCTOBER
Ocean 8328°
8027°  7021°
NOVEMBER
Ocean 7926°
7624°  6518°
DECEMBER
Ocean 7625°

The “Village of Islands” awaits you: Islamorada vacation rentals by owner


Sunny, friendly Islamorada is a smart choice for those who want a quiet escape away from the hustle and bustle of the major Florida hot spots. Located between Mile Marker 91 and Mile Marker 74, Islamorada is situated halfway between Miami and Key West along Florida’s scenic Route 1. Islamorada itself is spread out over six islands, each surrounded by tranquil ocean and soft sands.

Next time you’re looking for fun & sun, skip the traditional beachside hotel and opt for a vacation rental in Islamorada instead from FloridaRentals.com. When staying in a beach condo instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our rentals even come with special amenities like a backyard pool, washer/dryer units, and bicycles. Whether you’re looking for a super-sized modern villa with an indoor pool, or a cozy beachfront bungalow, you can find it on our site.

Islamorada, Florida travel advice


This destination is a tropical paradise for those looking to get away from it all. In fact, celebrities have made the secluded Islamorada a second home for decades, including the island’s most famed resident, baseball player Ted Williams. Be careful, or you might just fall in love with the area, too.

With a tropical climate and daytime temperatures that rarely dip below the 70s (F), Islamorada is a fantastic vacation spot any time of the year. During the summer, temperatures typically hover in the upper 80s. The ocean breeze cools temps down in the afternoon, and the conditions are just perfect for fishing (more on this below).

Getting here from Miami International Airport or Key West Airport is easy with a rental car, and the views on Route 1 and connecting bridges are incredible. Worth the drive! Once you’ve arrived, island hopping via boat is a fun way to see the entire area.

Named by early Spanish explorers, Islamorada literally translates to “purple isles” – a nod to the colors one might see during one of the legendary sunsets.

Top activities and attractions


The sport fishing capital of the world, this city offers activities for anglers of all ages and skill levels. The surrounding ocean and shallow bays teem with a variety of fish, including sailfish, bonefish, swordfish, marlin and tarpon. Hop aboard a deep sea fishing charter to try your hand at grabbing one of these fish and cooking your own catch for dinner. If you’d rather stay on land, explore try fly fishing in the backcountry.

Fishing not your thing? That’s fine, there’s plenty of other activities in the area. Grab a towel and head to Anne’s Beach for a full day of sand castles and snorkeling. It’s also private and quiet, so you will feel a long way away from the crowds on South Beach. If you’re feeling adventurous, try your hand at kite surfing since the shallow waters here provide an ideal environment.

Bring your family to the Theater of the Sea and take a live snorkeling tour or swim with dolphins. If you prefer nature surroundings, Windley Key Fossil Reef Geological State Park has nature trails for hiking. Don’t miss the underwater shipwreck site at San Pedro Preserve where scuba divers love the scenery and adventure.

Music lovers enjoy warm, tropical evenings and daylong music festivals on the lawn of the outdoor, waterfront ICE Amphitheater located inside Islamorada Founders Park, a 40-acre expanse that features an Olympic-sized pool, shallow water beach, water sports rentals, ball fields, fishing jetty, exercise opportunities, skatepark and a dog park.

Dining


Known for delicious seafood, Islamorada’s restaurants serve up the day’s freshest catch. Starting at breakfast, stop in to the Midway Cafe & Coffee Bar where guests can start their day off with an omelette or pancakes. For lunch, grab a wrap at Chef Michael’s where they feature daily seafood dishes that “wow” eaters. Want to eat with a view? Grab an outside table at Morada Bay and watch the palm trees sway as you grub. Lastly, the Green Turtle Inn has more seafood dishes and soups that come with rave reviews.

Islamorada homes for rent on FloridaRentals.com


Islamorada condo rentals on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!