Islamorada Vacation Rentals

(63 rentals)
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: Book now with 20% off | Nov 2019 - May 2020 | Email us at: info@ "FL2923"

$250

per night

View Details

Key Amenities

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

About this property

This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies ...

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Property Type

Islamorada House

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Tranquil waterfront 2/2 villa with private roof terrace, boat ramp & dockage!

1 BR | 2 BA | Sleeps 4 | Quick View

8

Distance to beach: 5 miles to Anne's Beach

$185

per night

View Details

Key Amenities

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

About this property

Please note rentals are 3 nights minimum. Longer term rentals are welcome.The "Nest" villa (MM 82.3) is a private villa residence which is wonderfully maintained. It is the total upper floor of the building in the foreground in the photos. The property is well located off the beaten track ...

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Property Type

Islamorada Condo

"Mark and Dolly"
Reviewed July 15, 2018

Absolutely fantastic place to stay, we will definitely be back

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Waterfront Paradise on Canal W/New Pool

$355

per night

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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

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Luxury Home with Dock, Waterfall Pool, HotTub, Wi-Fi deep water dock up to 60 ft

$400

per night

View Details

Key Amenities

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

About this property

Venetian Shores 4-Bed/4-Bath Luxury Pool Home with 100' Dock & Opt. ElevatorMINIMUM STAY: 29 DAYS Dreaming of a Florida Keys vacation where you can boat, fish, dive, snorkel, or stay home and swim in your own private heated pool? This is it. This home offers a professionally-designed living environment ...

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Property Type

Islamorada House

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

$321

per night

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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

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Luxury Florida Keys Estate

3 BR | 3 BA | Sleeps 8 | Quick View

$714

per night

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Key Amenities

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

About this property

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 overlooking the Atlantic Ocean. Over 4,000 sq feet of ...

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Property Type

Islamorada House

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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$120

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

"Wonderful!"
Reviewed June 2, 2019

I have stayed here twice and can’t recommend this property enough! I struggled to write this because there are so many wonderful things about this little piece of paradise! The beach in unbelievably ...

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

per night

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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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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks & more

3 BR | 2 BA | Sleeps 6 | Quick View

6
Owner special: September and October 20% discount . It's a great vacation house.

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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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

1 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Founders Park

$214

per night

View Details

Key Amenities

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

About this property

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air ...

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Property Type

Islamorada Condo

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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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sea oats beach

5 BR | 5 BA | Sleeps 14 | Quick View

$180

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

One of the only white sandy beaches in the Fl Keys and 1 mile whole of it!Newly built,state of the art,beautifully done 5 bedroom home, 4 master suites w/ king beds and facing open water! Magnificent indoors and out! Each bathroom is exquisite,very large stone,glass and hand picked tiles. The ...

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Property Type

Islamorada House

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Keys Cottage; Remodeled Villa in Native Hammock on Florida Bay

$214

per night

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Key Amenities

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

About this property

The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove ...

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Property Type

Islamorada Cottage

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Mitchell's Keys Villa - Private, Secluded House on the Bay

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 5 miles to Five Miles

$185

per night

View Details

Key Amenities

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

About this property

Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a quiet residential area (rare). The villa is approx. 50 feet from the water. The property contains a wading beach and a free marina with night lights, power and water.The villa itself ...

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Property Type

Islamorada House

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Gulfview Getaway - Bayfront Home with Private Beach and Dock!!

$317

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 28 Days"Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on ...

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Property Type

Islamorada House

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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

$250

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 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 will make you ...

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Property Type

Islamorada Condo

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

$117

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

$269

per night

View Details

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

$357

per night

View Details

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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PALMS #313

2 BR | 2 BA | Sleeps 4 | Quick View

$73

per night

View Details

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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Blue Water Retreat - Location!!!! Gorgeous house with Pool and Ocean Views.

$183

per night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from ...

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Property Type

Islamorada House

"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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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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FALL DISCOUNTED PRICES!! BAYSIDE CONDO

$86

per night

View Details

Key Amenities

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

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for your ...

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Property Type

Islamorada Condo

"Great location and condo"
Reviewed July 19, 2019

This is a great place with an awesome owner. Location is great for boating and fishing. Will be back!

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

$357

per night

View Details

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

1 BR | 1 BA | Sleeps 2 | Quick View

2

Distance to beach: 12 miles to Founders Park

$143

per night

View Details

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

"Nice little getaway."
Reviewed March 30, 2019

Nice quiet little getaway. Enjoyed staying there. Has pretty much everything you need . Would rent there again.

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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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My Paradise - Oceanfront beach house with protected dockage.

$227

per night

View Details

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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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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Antigua Place - Charming vacation home located in Port Antigua.

$173

per night

View Details

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

$113

per night

View Details

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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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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Pool Home Fisherman's Dream Ocean Side

$150

per night

View Details

Key Amenities

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

About this property

4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family friendly and a fisherman's dream. Our home sleeps 8 (max) with every comfort you would want while on vacation in the keys...Large ...

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Property Type

Islamorada House

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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
  • Pet 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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Sunshine Place - Ground Level Unit with Ocean Views.

$180

per night

View Details

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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Island Living with Gulf Views

2 BR | 2 BA | Sleeps 4 | Quick View

$114

per night

View Details

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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Anglers Reef-Rent Now for Summer- May/June Special

$243

per night

View Details

Key Amenities

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

About this property

Welcome to Anglers, a newly renovated luxurious escape for your vacation needs. Perfect for families, couples, or a friends getaway. Located in Anglers Reef, a gated community with heated swimming pool and two private beaches. Our availability calendar is always up to date and current.Our beautiful ...

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Property Type

Islamorada House

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Oceanfront End Unit, Pool, WiFi, Panoramic Ocean Views

2 BR | 2 BA | Sleeps 4 | Quick View

4

Distance to beach: 1 miles to Harry Harris

$107

per night

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Key Amenities

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

About this property

INCREDIBLE SPECIAL RATE: SEPT 7 - 14, 2019Welcome to this 5th floor end unit condo in an art deco inspired building right on the Atlantic Ocean in a peaceful neighborhood. Enjoy full panoramic ocean views right from your own condo and balcony. Oceanfront clean heated pool and private covered parking ...

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Property Type

Islamorada Condo

"Gorgeous view"
Reviewed June 22, 2019

The best condo that we've ever stayed at. An absolutely amazing view. This condo was well stocked with everything that you might have forgotten. It felt like home.

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DIRECT OCEANFRONT POOL HOME W/ Deep Water 70ft dock, Huge Saltwater Heated Pool!

4 BR | 3 BA | Sleeps 12 | Quick View

1
Owner special: Book now with 20% off | Nov 2019 - May 2020 | Email us at: info @ "FL2923"

$400

per night

View Details

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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Pool Home - Fisherman's Dream! Summer Special

$167

per night

View Details

Key Amenities

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

About this property

This beautifully furnished waterfront home with ocean views will thrill the most ardent diver or fisherman and his family. You will love the luxury of a heated pool, magnificent view, and protected deep water dockage for multiple boats. It is located on a large harbor with multiple sailing yachts and ...

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Property Type

Islamorada House

"Unforgettable family vacation"
Reviewed January 3, 2019

My husband and I rented this house this past month, along with our 7 adult kids/significant others. (9 of us in total) We absolutely loved it. The house itself was perfect. Very clean, and up to date. Had ...

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"Tommy Bahamma" Summer Specials!

$93

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Located at Mile Maker 87 Bayside. This gated condo complex offers a large heated pool, club house, Jacuzzi, two tennis court, large Bayside beach. This townhouse (sleeps 8) has just been totally renovated with beautiful tropical furniture, all new kitchen, small garden patio with hammock, living room ...

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Property Type

Islamorada House

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Canal apartment overlooking beach with exclusive occupancy in private home

$117

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

The apartment is in house on the canal and across from the beach with beach access. It is situated on the ground floor of a two story 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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Islamorada 3/2 Canalfront with Pool and Dockage...Peaceful

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2000 feet to White Marlin

$400

per night

View Details

Key Amenities

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

About this property

Come visit Islamorada and enjoy a solar heated pool with Jacuzzi! You will also have access to a private homeowner's sandy beach! The sunsets are incredible! Come to paradise and relax in this Islamorada 3/2 with dockage. Bring your boat; you are just 20 minutes to the Atlantic and open Gulf. Everglades ...

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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!