Islamorada Vacation Rentals

(76 rentals)
Sea Ranch

4 BR | 3 BA | Sleeps 8 | Quick View

$1286

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool

About this property

Mile Marker 83 – OceanfrontTwo adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and skiff dock. Relax at the beach or cool down in the beachside pool.The front home ...

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Property Type

Islamorada Cottage

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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$179

avg/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

"Excellent getaway, beautiful setting your own beach, The evenings were the best."
Reviewed September 22, 2020

This was the perfect getaway spot for us. The apartment has everything you need and more. The owners were excellent and very accommodating. Nothing like having your own private beach to enjoy. We even ...

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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

avg/night

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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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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

avg/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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Large Oceanfront condo with stunning views of Atlantic Ocean

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.3 miles to Founders Park

$217

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront

About this property

Spacious 3 bedroom/ 2 bathroom condo on the Atlantic ocean with large screened patio on second floor; private underground parking, oceanfront pool and beach, tennis, pickle ball, protected marina with boat ramp, Elevators for easy access to beautiful ocean views. Close to restaurants, shopping, hiking ...

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Property Type

Islamorada Condo

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

avg/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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Keys House with Deep Water Dock

3 BR | 3 BA | Sleeps 8 | Quick View

1

$621

avg/night

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Key Amenities

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

About this property

Gorgeous three story home completely remodeled and refurnished using tropical island type colors and décor. Located on one of the only true deep water canals in Islamorada, this house is only a few lots in from Snake Creek with great views on the second and third floors.Just a quick review ...

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Property Type

Islamorada House

"Amazing location, super clean and spacious house, huge pool"
Reviewed October 15, 2019

We stayed here with our family and it was an excellent trip. The dock was huge and the canal is really deep. We brought a 30 foot center console boat and caught a lot of fish. The owner Tony was really ...

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

$200

avg/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

"Florida keys"
Reviewed October 10, 2020

Heaven on Earth , Can't wait to return . Annual Birthday trip with family and friends . Relaxing , fishing , feasting and enjoying good company in a beautiful location . Highly recommend

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Waterfront Paradise on Canal W/New Pool

$355

avg/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

"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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Gorgeous waterfront home

3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

avg/night

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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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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks Kayaks

3 BR | 2 BA | Sleeps 6 | Quick View

6
Owner special: Last minute cancellation , available October 22 to November 20, anytime in between .

Distance to beach: 0.5 miles to White Marlin Beach

$510

avg/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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Nautilus Getaway

3 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to White Marlin Beach

$240

avg/night

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Key Amenities

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

About this property

**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will feel like you just walked into a comfortable, cozy home. With its cool ...

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Property Type

Islamorada House

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

$304

avg/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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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

$426

avg/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 116D

3 BR | 1 BA | Sleeps 6 | Quick View

$414

avg/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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Brand New Waterfront Home with Pool and Dock

$450

avg/night

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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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Blue Heaven Coastal Cottage

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach

$217

avg/night

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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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Ocean Harbor M31

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Founder's Park

$283

avg/night

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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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Greenflash

4 BR | 4 BA | Sleeps 8 | Quick View

$600

avg/night

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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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Waterfront In Islamorada

2 BR | 2 BA | Sleeps 6 | Quick View

$219

avg/night

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Key Amenities

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

About this property

Enjoy this spacious 2 bed/2 bath waterfront town home with an open floor plan and relaxing views of the lagoon. Catch an amazing Keys sunset while you BBQ from our over-sized patio! Swim at the private beach, salt water lagoon or 2 pools, Enjoy the playground, tennis courts, riding bikes, fishing off ...

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Property Type

Islamorada Townhome

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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

$284

avg/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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Apartment with beach access.

1 BR | 1 BA | Sleeps 2 | Quick View

$152

avg/night

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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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LITTLE BAY - Upper Duplex -A 2nd Floor Duplex on Gated Bayfront Shared Property

$429

avg/night

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Key Amenities

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

About this property

Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps ...

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Property Type

Islamorada House

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

$263

avg/night

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Key Amenities

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

About this property

Minimum Rental: 3 MonthsPelican 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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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

$179

avg/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

avg/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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BEACON REEF #503 - Stunning Newly Renovated Condo in Oceanfront Complex

$166

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

$146

avg/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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Antigua Place - Charming vacation home located in Port Antigua.

$187

avg/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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Island Conch Cottage

2 BR | 1.5 BA | Sleeps 4 | Quick View

6

Distance to beach: 0.5 miles to Anne Beach

$132

avg/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

"ANOTHER GREAT EXPERIENCE !!!"
Reviewed September 21, 2020

This is my fourth year visiting Islamorada. Something that I look forward to each year. And every year I book this Cottage , I won't stay anywhere else!! It's always clean. If there is anything you need ...

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BAYSIDE CONDO WITH MARINA,POOL AND BEACH

$158

avg/night

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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

"Vacation in Islamorada"
Reviewed October 16, 2019

Our stay in Futura Yacht Club was wonderful and Islamorda is a vacation paradise. There is so much to do .... snorkeling the beautiful Alligator Reef , feeding the Tarpon at Robbie's , to an exquisite dinner ...

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LITTLE BAY - Lower Duplex - Ground Level Unit on Gated Bayfront Shared Property

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Founders

$429

avg/night

View Details

Key Amenities

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

About this property

Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up ...

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Property Type

Islamorada Apartment

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

$181

avg/night

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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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Little Bay - Entire Compound in Islamorada w/Gorgeous Bay Views and Boat Basin

6 BR | 6 BA | Sleeps 18 | Quick View

Distance to beach: 5 miles to Founder's Park

$1250

avg/night

View Details

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

$142

avg/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

"Island Getaway"
Reviewed August 10, 2020

Staying at the Beacon Reef was a great getaway for the month of July. Its nearby lots of restaurants and has a Publix right across the street. We are definitely coming back next year for the month of July.

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BEACON REEF 301 - Gorgeous NEWLY UPDATED Condo with Ocean and Garden Views

$154

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront

About this property

MINIMUM STAY: 28 DAYS NEW TO RENTAL MARKET “Beacon Reef 301” is a fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, clean, spacious 2 bedroom 2 bath condo ...

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Property Type

Islamorada Condo

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PALMS 417 - 1 Bedroom Condo with Tropical and Florida Bay Views

$90

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront

About this property

Minimum Rental: 1 Month Everything in this unit is lovely - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch ...

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Property Type

Islamorada Condo

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PALMS 301 - 2 Bedroom Condo with Lovely Ocean Views from Balcony

$112

avg/night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 Days "The Palms #301" is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure ...

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Property Type

Islamorada Condo

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

$129

avg/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 Bedroom Condo with Ocean, Pool, and Tropical Views

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Founders

$112

avg/night

View Details

Key Amenities

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

About this property

NEW LISTING 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 ...

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Property Type

Islamorada Condo

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

$161

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

$96

avg/night

View Details

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

"Lovely little home on a quiet street"
Reviewed August 29, 2020

I rented this so I could have a quiet place to swim and relax before undergoing major surgery. The pool area is a perfect oasis with the occasional visiting birds and squirrels. The house is comfortable ...

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Palms #309 - Exceptional condo with panoramic views of the Atlantic Ocean.

$119

avg/night

View Details

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

4 BR | 3 BA | Sleeps 12 | Quick View

1

Distance to beach: 5 miles to Founder's

$543

avg/night

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Key Amenities

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

About this property

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

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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 406 is a Charming 2 Bedroom Condo with Views of the ocean & Complex

$131

avg/night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. "Beacon Reef 406" is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient to ...

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Property Type

Islamorada Condo

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Sunshine Place - Ground Level Unit with Ocean Views.

$195

avg/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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PALMS #313 Spectacular 2 Bedroom Condo with Breathtaking Oceanfront Views

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 7 miles to Founders

$124

avg/night

View Details

Key Amenities

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

About this property

MINIMUM STAY: 1 Month 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 ...

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Property Type

Islamorada Condo

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BEACON REEF 306 - 2 Bedroom Condo with Gorgeous Views of the Ocean and Complex

$131

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 1 Month Enjoy a relaxing summer and fall here in the Keys at this immaculate and charming two bedroom and two bath condo with screened balcony overlooking views of the tropical complex and of course the beautiful ocean. While the owners attend to their other property "up north" ...

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Property Type

Islamorada Condo

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BEACON REEF 501 - Updated Condo in Oceanfront Complex in Islamorada

$143

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You’ll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 – granite counters, stainless steel appliances, and ...

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Property Type

Islamorada Condo

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FISH WHISTLE - Stunning Bayfront Home Directly on Snake Creek. Dock, Pool&More!

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 2 miles to Founder's Park

$522

avg/night

View Details

Key Amenities

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

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!