Islamorada Vacation Rentals

(95 rentals)
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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries.Escape to the ultimate paradise at our stunning oceanside estate in the Florida Keys. This majestic property ...

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Property Type

Islamorada House

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 3 miles to Anne's Beach State Park

$313

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your ...

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Property Type

Islamorada House

"Breathtaking views!!"

The views are amazing with beautiful sunsets every evening. The roof top gives a spectacular view of the night sky. During the day swimming, kayaking, boating, fishing, and snorkeling are just steps from ...

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$974

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Welcome to the “Sailfish House” at Tarpon Point!Soak up the sun and take in the spectacular views at this opulent 4 bedroom, 4 bath home located in the private community of Tarpon Point. Accommodating up to eight adults, this impressive home makes it easy to both entertain and unwind with ...

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Property Type

Islamorada House

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5 BR | 3 BA | Sleeps 12 | Quick View

1

$533

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Beautiful 5 bedroom pool home with 70 foot of dockage at mile marker 74.5 on the bay side. The first floor is a private apartment with two bedrooms, one has a queen and the other two queens. Has a full kitchen, living room, dining area and full bathroom. The second floor has three bedrooms, two with queens ...

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Property Type

Islamorada House

"Summer vacation"

Owner easy to work with, place is nice and clean, is as described. My kids especially enjoyed all of the iguanas that are running around.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Beautiful Oceanfront Condo"

Plantation by the Sea is an older condo complex that is beautifully maintained. The condo is located at MM 87.5 just off of U.S. 1 in the heart of Islamorada. Restaurants of various types can be found within ...

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4 BR | 4.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.5 miles to White Marlin Beach

$759

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Bring your boat and Jet SkisNestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, double jet ski lift, and two floors facing ...

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Property Type

Islamorada House

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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 50 yards to Private sunning beaches at Anglers

$686

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Vacation Rental License 097. Welcome to Anglers Reef, a very special community of vacation homes. And to Anglers Reef 140's OceanFRONT location with its unique UNOBSTRUCTED OCEAN VIEWS FROM EVERY ROOM and spacious wraparound decks!Boat slip is optionally available for $375/wk, Christmas and ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community ...

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Property Type

Islamorada House

"OUTSTANDING ON SO MANY LEVELS"

The magic began with the excellent, attentive, and kind correspondence with the owners. So excited for us to enjoy their home. Upon arrival, the magic continued. The photos you see are exactly what ...

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3 BR | 3 BA | Sleeps 10 | Quick View

Inquire for rates

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

Beautiful home, facing ocean views indoors and out! The house affords breath taking views of the atlantic ocean, Snorkel right off the shore line or fish right at the end of the dock for many you are a boater bring your boat and enjoy excellent fishing straight out of the dockage, the depth at low ...

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Property Type

Islamorada House

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2 BR | 2 BA | Sleeps 4 | Quick View

12

Distance to beach: 5 miles to Anne's Beach

$299

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

The "Nest" villa (one of 7 privately owned condo residences) sits on a 1 acre lot located on Islamorda's beautiful Florida Bay. Stunning water views and unforgettable sunsets are guarenteed. The property is filled with mature tropical landscaping along a tree lined private gravel driveway ...

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Property Type

Islamorada Villa

"paradise package, bring your boat!"

clean, up to date , and stocked up for guests. your own personal marina, and sunsets to die for! trimming trees would be my only advice .view of water ( Bay) blocked by tree line... loved staying there ...

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3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

avg/night

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Key Amenities

  • Air conditioning
  • 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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

See why we have ALL 5-star reviews! Located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries.As soon as you step foot in this stunning two-floor home, you're greeted by a gorgeous yet highly comfortable modern open-floor plan living area. ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Love this house"

Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient. ...

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4 BR | 3 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$286

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

PROPERTY NAME: Harbor House 101 San Juan Dr., Islamorada, FLLOCATION: Bayside Canal home located in the Upscale Venetian Shores CommunityMINIMUM STAY: 28 DaysMILE MARKER: 86DETAILS: Ready for occupancy this winter! This is a very special single family home with many amenities. Relax on ...

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Property Type

Islamorada House

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3 BR | 2 BA | Sleeps 6 | Quick View

9

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6 Pure High End Luxury with all the Bells and Whistles Boat Friendly Vacation Rental with DockVilla 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. ...

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Property Type

Islamorada House

"Perfect, quiet, and secluded"

This was a spectacular vacation! The house was clean and comfortable, and the location was quiet and the setting perfect. I could write a novel about the host and the house, but in a few words the host ...

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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

"A slice of paradise"

This place is perfect for a peaceful stay! The beach is right outside the room! We saw dolphins playing in the mornings, snorkeled off the beach, and had the chairs and hammock provided. The location ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • 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

"Perfection in paradise!"

This was a perfect house! Easy and quick access to ocean and gulf, docked 35’ boat right at the house, large pool with hot tub, plenty of parking for vehicles and trailers, very clean, well stocked, tiki ...

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$475

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet 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

"Great Pool Rental!"

This was a great house! Our whole family enjoyed the stay very much. It was quiet and the layout of the home is perfect for multiple families to stay. The pool area was very nice and the dock is a perfect ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

COMING SOON - Beautiful new home on Florida Bay with sandy beach, large pool, beautiful views and sunsets all year round. Private suites are offered for 2-4 people each with king bed, private bath and mini kitchen facilities. Estimated availability February 2024. Monthly bookings only - no pets please. ...

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Property Type

Islamorada House

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3 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach State Park

$857

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

This stunning top floor end unit in Bay Harbour has stunning ocean and harbor views and includes a 50ft. boat slip! BAY HARBOUR ALLOWS 7-DAY RENTALS . The interior design is spectacular. Coffered ceilings in the living area, top of the line Miele and Thermador appliances, custom kitchen cabinetry, intricate ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house ...

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Property Type

Islamorada House

"4 years"

This was our 4th year on Tollgate and somehow it gets better. Tiff and Bill go above and beyond in accommodating us. The updates look fabulous, love the painting in the dining room. Our dog Max has made ...

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 100 feet to Front door

$216

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

MINIMUM STAY: 30 daysSpacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip.Walk out your front door and go boating.You’ll ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

3 Beds/2 bath townhouse in Islamorada, Florida Keys. Ground Floor features a full kitchen, full bath, living room with large tv, dining room with views of the tennis court, outdoor patio with BBQ and additional dining table. Second Floor features a large full bath, 1 king size bed, 1 queen size bed, 2 ...

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Property Type

Islamorada Condo

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3 BR | 2.5 BA | Sleeps 6 | Quick View

$590

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Beautiful views from this condo!Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL.We are new owners of this condo that has never been in the rental pool. (that is why few reviews)Complete remodel with no expense spared!The location is quiet with the most beautiful ...

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Property Type

Islamorada Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

ALERT: BRAND NEW POOL JUST COMPLETED AND INSTALLED....DOWNSTAIRS IS AVAILABLE TO RENT BUT IS NOT INCLUDED IN THE PRICE feel free to ask about downstairs pricing and availability. Downstairs is an additional 3br and 2ba so the upstairs and downstairs would be a total of 7br & 4ba....THIS LISTING ...

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Property Type

Islamorada House

"A month in heaven"

My wife and I spent the month of Dec. 2022 at this property in Islamorada (HEAVEN) in the Keys. The property has a pool, a canal and a boat dock that can handle any boat.Let me start of saying that ...

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$898

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Introducing the "Bonefish House" at Tarpon Point!This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

‘The Beach House’ at Tarpon Point in Islamorada‘The Beach House’ is a luxurious oceanfront home in a private gated enclave of only 12 houses. This end home offers privacy and beautiful ocean views including of Indian Key Historic State Park. Enjoy morning coffee and a phenomenal ...

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Property Type

Islamorada House

"Perfection!"

Beautiful home, gorgeous views….this home has everything and more! We have been vacationing in Islamorada for the past 10 years and have rented many different places, but this was by far the nicest and ...

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5 BR | 5 BA | Sleeps 10 | Quick View

$700

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • 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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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Pool

About this property

$14,000-$16,000 Weekly, Call for holiday rates Maison Residences offers world-class oceanfront residences in the Florida Keys. Unit 102 at Maison Residences is a luxurious property offering sweeping views of the Atlantic Ocean from the kitchen, grand room, master bedroom, and oversized living terraces. ...

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Property Type

Islamorada Condo

"Spectacular!"

Hurricane Ian brought us to Islamorada for the first time. We had to move our daughter's wedding over here and needed a 4 bedroom home for our family. We definitely made the right choice with Maison 102. ...

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 7 miles to Anne's Beach State Park

$333

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

This 3-bedroom condo couldn't be any closer to the ocean. Located on the 4th floor at Palms of Islamorada this unit takes full advantage of the waterfront setting. There are two bedrooms with open water views overlooking the blue waters with Alligator lighthouse off in the distance. Both of these ...

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Property Type

Islamorada Condo

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3 BR | 2.5 BA | Sleeps 6 | Quick View

$492

avg/night

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Key Amenities

  • Air conditioning
  • 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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3 BR | 2 BA | Sleeps 6 | Quick View

$233

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assigned boat slip in private marina just around the corner. All new kitchen, baths, porcelain tile flooring, fully furniture and LOTS more. Three bedrooms, two bath home on a peaceful plugged ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

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Property Type

Islamorada Condo

"Wonderful"

I highly recommend this vacation spot. Not only is the condo very nice the whole property is set up for your every need. The owner and property manager are very nice and accommodating. I was amazed by the ...

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$500

avg/night

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Key Amenities

  • Air conditioning
  • 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

"We love this house!"

2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$453

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Mother Ocean!This stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room ...

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Property Type

Islamorada Condo

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3 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach State Park

$509

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

This Condo is located on Lower Matecumbe Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Bay Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a second floor location make it easy to enjoy your stunning view ...

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Property Type

Islamorada Condo

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4 BR | 4 BA | Sleeps 10 | Quick View

3

Distance to beach: 2 miles to Founders Park

$875

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

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

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Property Type

Islamorada House

"You found it"

If you’re looking for a well kept beautiful home, right on the water positioned right between the Gulf and Atlantic, great pool and hot tub YOU FOUND IT. Communication is great and owner is so helpful. ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Ground level 3/2 Flat with wrap around screened in lanai in gated community. 3/2 Split Floor Plan: Master Suite with 2 sinks. separate shower/tub and toilet closet Queen Bedroom separated by bathroom and shower/tub with 2 Twin Bedroom. Left wing (Queen, Twin, and separate bathroom) closes off to ...

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Property Type

Islamorada Condo

"Wonderful visit"

Just wanted to say what a wonderful time my family and I had at your property in Isla Mirada. The condo was very conveniently located and it was great that we could just walk across the street to go eat ...

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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.3 miles to Anne's Beach

$140

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Private pool
  • Rentals by owner

About this property

Enjoy this modern lagoon front ground level one bedroom condo/apartment with exclusive use of the backyard, pool, dock and carport. Located on the Gulf side of Lower Matecumbe (Islamorada MM 73.5) minutes from the Channel 2 and Channel 5 Bridges offering immediate access to Ocean side. Dockage available ...

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Property Type

Islamorada Condo

"A month in paradise!"

After staying in St. Pete Beach for a month, we decided to go south and visit the Florida keys. We found Bill and Carolyn's place on Florida Rentals and decided to give it a go. What a wonderful experience!The ...

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach State Park

$392

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

This updated Port Antigua home with 85 ft. of concrete dock is ready for a new family to enjoy. The open floor plan and vaulted ceilings make this house feel so welcoming! French doors with side lights let in the natural light and open to the lanai where you can enjoy your morning coffee or a cocktail ...

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Property Type

Islamorada House

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2 BR | 2 BA | Sleeps 4 | Quick View

4

$357

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

This Condo is located on Lower Matecumbe Key, close to restaurants, shopping and Tiki bars. With pool, tennis courts and a protected marina, Bay Harbour is a preferred residence for repeat visitors to the Keys. Elevators for easy access and a second floor location make it easy to enjoy your stunning view ...

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Property Type

Islamorada Condo

"Bay Harbor 303"

The condo was lovely! Thoroughly furnished. Updated amenities. Beautiful grounds. On-site staff. Friendly and helpful. Highly recommended

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6 BR | 4 BA | Sleeps 12 | Quick View

3

Distance to beach: 0.5 miles to Port Antigua Private Beach

$440

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

This recently renovated property enjoys 6 bedrooms, 4 bathrooms and separate kitchens, living rooms and laundry facilities. It shares an ocean facing veranda with 2 dual gas grills and multiple seating and lounging areas. It has ample offstreet parking for vehicles and trailers. The Admiral on the Cove ...

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Property Type

Islamorada Townhome

"A Spectacular Spot"

We enjoyed our stay at this beautifully furnished and well stocked house. George and Bonnie responded quickly to any questions that we had. The separate living areas allowed us to enjoy family and friends ...

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1 BR | 1 BA | Sleeps 2 | Quick View

5

$199

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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

"Perfect rental for one couple"

This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under ...

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3 BR | 3 BA | Sleeps 6 | Quick View

$689

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Welcome to “At The Sandbar!”This newly built oceanside villa in Islamorada is a wonderful choice for those seeking a serene retreat and an opportunity to immerse themselves in the relaxed nature of the Florida Keys. Situated within the Peaceful Palms community on Windley Key, this three-bedroom, ...

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Property Type

Islamorada Villa

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2 BR | 2 BA | Sleeps 4 | Quick View

6

Distance to beach: 0.9 miles to Founders Park

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom ...

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Property Type

Islamorada Condo

"Perfect!"

Sharon’s condo was absolutely gorgeous! It was super clean upon arrival and had everything we could have needed for our 3 month stay (linens, dishes, pots & pans, cleaning supplies, etc). The interior ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to the "Keys Life Cottage!"This beautifully updated and spacious two bedroom, one bath home is tucked away on a large landscaped lot in the heart of Islamorada and within walking or biking distance to Islamorada's famed Arts and Cultural district and to some of the most renowned ...

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Property Type

Islamorada Cottage

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located ...

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Property Type

Islamorada Townhome

"Lazy Daz Beac House"

Excellent couple to work with. Great communication. The rental was beautiful and clean. We had a problem with the rental and they communicated with us and together we solved the problem. They went over ...

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1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 1 miles to Anne's Beach

$200

avg/night

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Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

Secluded Waterfront Apartment 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 sure 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 ...

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Property Type

Islamorada Apartment

"Little piece of paradise!"

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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 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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Great Home Away From Home!"

Perfect location! Our family had a great week and we will definitely come back. Condo is well furnished, clean and plenty of space. Kitchen is well stocked with essentials. Pool was very refreshing. The ...

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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°

Find Your Ultimate Vacation with Islamorada Vacation Rentals


Islamorada is a small village located south of mainland Florida along the state’s gorgeous tropical keys. In fact, Islamorada vacation rentals and the village in which they reside encapsulate six of the Florida Keys and is known as one of the most beautiful vacation destinations throughout Florida. 

Plus, Islamorada is often called the “Sport Fishing Capital of the World,” making it a great place to visit for those who enjoy fishing for sport or recreation. 

Due to its separation from mainland Florida, Islamorada is made up mostly of white-sand beaches and clear waters, which offer plenty of opportunity for some peaceful R & R as well as all of the oceanside water sports you could imagine. 

Swim with the dolphins, take a snorkeling excursion, ride the waves on your surfboard, or simply relax on the beach with a good book; whatever you choose to do, you’re sure to have an incredible experience in Islamorada. 

In a village as unique and special as Islamorada, the best way to get the most out of your vacation is to browse Islamorada vacation rentals instead of opting for a hotel.

Hotels are crowded and impersonal, but your Islamorada home rental will be a one-of-a-kind space completely dedicated to you and your family. Plus, you’ll be able to live the life of a local and enjoy the unique architecture of the Florida Keys from a new perspective in your Islamorada rental home.

How to Get the Most out of Your Islamorada Vacation


As a tropical location, Islamorada sees steady rainfall throughout the year as well as relatively high levels of humidity, especially in the summer months. The rainiest seasons tend to be early summer and early autumn, making springtime and late autumn the best times of year to visit Islamorada in order to enjoy the best possible weather. 

Since the Florida Keys are separated from mainland Florida by several miles of ocean, most tourists will access the islands by air instead of by car, even if they’re already Florida residents. 

The Florida Keys/Marathon International Airport is the easiest way to access the city, and vacationers can reach Islamorada from the airport within a 40-minute drive by way of the Overseas Highway.

Best Activities Nearby Islamorada House Rentals


You can’t get much closer to ocean wildlife than on the Florida Keys, which is why Islamorada’s Wild Dolphin Tours are so wildly popular. 
Get to know the resident dolphins of the Florida coast by swimming alongside them and experience many other incredible types of aquatic creatures from a close range, all guided by locals who know the waters of the Florida Keys inside and out. 

With Wild Dolphin Tours in Islamorada, you can also opt to take a snorkeling excursion along the scenic coral reefs surrounding the islands with the Snorkel & Sandbar Boat Tours. 

These excursions include Alligator Reef, Florida Bay, and Cheeca Rocks, some of Florida's most stunning and highly sought-after coral reefs. Book a three-hour, four-hour, or private tour to create a one-of-a-kind experience for you and your family. 

There’s plenty more natural beauty to see in Islamorada apart from the expansive ocean views. Nature lovers will enjoy a trip to the Lignumvitae Key Botanical State Park, a unique botanical experience that features a variety of local plant life and even some opportunities to view Florida Keys wildlife. 
The park is open from 8 a.m. to 4 p.m. Thursday through Monday, and the entrance fee is $2.50 per person, with self-guided tour brochures available to get the most out of your visit. 

Looking to take in a bit of local history as you enjoy the gorgeous scenery? Pay a visit to Indian Key Historic State Park, the site of the original Dade County seat in 1836. 
In 1840, a group of local natives led by leader Chakaika raided the settlement and burned the town to the ground, leaving only one building behind. You can visit the remaining town building and learn more about the area’s unique history any day of the week between 8 a.m. and sunset, and the entrance fee is $2.50 per visitor.

Islamorada, FL, Annual Events


Island Fest is one of the most anticipated annual events in Islamorada. Taking place early each April, Island Fest features an art show and competition, unique food vendors, live music, a classic car show, and more. Plus, local food vendors go head-to-head to earn the sought-after People’s Choice Award for the best food of the festival. 
Another popular Islamorada event more heavily focused on the local art scene is the Morada Way Art Walk, a monthly event that showcases local art in a variety of mediums, including photography, painting, ceramics, and printmaking. The Morada Way Art Walk also features live musical acts and delicious dining options and is free to enter.

Best Food and Drink near Islamorada Rentals


If you’re looking to enjoy a fine meal with an unforgettable view of the ocean, there are many incredible options to suit your needs in Islamorada. Locals and visitors alike love Lorelei Restaurant & Cabana Bar, a fun semi-casual joint that serves a variety of fresh seafood entrees and boasts a full bar with unique cocktails to try. 

Islamorada also features the Islamorada Brewery & Distillery, the only establishment of its kind on the Florida Keys. Experience all that Islamorada has to offer with an incredible locally brewed beer in the beer garden, a refreshing hand-crafted cocktail, and delicious eats from local food trucks.


FAQ

How many vacation rentals are there in/around Islamorada?

There are 95 Islamorada vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Islamorada?

There are vacation rentals available in Islamorada for as low as $88 per night with an average price per night of $390.

Can I rent a house in Islamorada?

Yes, you can find house rentals in Islamorada close to Theater of the Sea, Florida Keys Brewing Company, and History of Diving Musem. Don't forget to stop in to Founder's Park or Alligator Reef.

Do any vacation rentals in Islamorada have a pool?

Yes there are 40 vacation rentals with a pool in Islamorada on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Islamorada vacation rentals on the ocean?

There are 40 oceanfront rentals in Islamorada available on FloridaRentals.com. Use our filters to search and book yours today!