Islamorada Vacation Rentals

(110 rentals)
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Islamorada Cottage
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1 bathroom

$156

avg/night

$156
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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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Islamorada Apartment
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms

$129

avg/night

$129
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Gorgeous 2 bedroom 1 & half condo, two story (townhouse style) HEATED POOL, DOCK FOR FISHING, OCEAN FRONT location. Gated community makes it a perfect getaway for a family for 4 but sleeps 6 to accommodate any short term visitors. Inside our home, you will find all the amenities for an enjoyable stay, ...

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Property Type

Islamorada Apartment

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Islamorada House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
4 reviews

$450

avg/night

$450
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

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

Featured review

"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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Islamorada House
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
1 review

Distance to beach: 5 miles to Founders Park

$87

avg/night

$87
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Half Duplex HomeAre you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and manatees ...

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Property Type

Islamorada House

Featured review

"Wonderful stay in the Keys!"

The screened in area and the outdoor space make this rental perfect! We kayaked on the canal, and walked around the neighborhood daily. We watched boats and manatees from the screened in porch. Lee (the ...

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Islamorada Villa
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

$500

avg/night

$500
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Mile Marker 75 – Bayside4 bedroom 3 bathPalm Cottage South, is a charming, modern home directly on the canal with a heated, private pool, dockage, and access to the Port Antigua community sandy beach. Dockage for 24′ boat max on the lift pictured.Elevated for great breezes and ...

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Property Type

Islamorada Villa

Featured review

"House was great with all the amenities!"

Great house, pool, and area. Lots of attractions and wonderful restaurants. Also, great people to work with.

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Islamorada House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$367

avg/night

$367
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Mile marker 77. Deep Water ocean side canal with direct access to the Atlantic Ocean and a straight shot to Alligator Light House. Sunny Patio and splash Pool. 4 Bedrooms/4 Baths. Sleeps 8. There is no cable package with this home so please bring your passwords for live streaming from the smart TVs.The ...

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Property Type

Islamorada House

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Islamorada House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms

$800

avg/night

$800
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Mile Marker 75 – BaysideLarge, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal.The main selling point of Latitudes is the home’s awesome outdoor area. Pool, Tiki Hut, grill and outdoor seating ...

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Property Type

Islamorada House

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Islamorada Condo
3 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 4 bathrooms

$733

avg/night

$733
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Mile Marker 83 – BayfrontWelcome to your dream waterfront rental home in Islamorada, located in the heart of the Florida Keys. This stunning 4 bedroom, 4 bathroom home sits on the bay and offers breathtaking views of the water and world class sunsets.As you enter the home, you’ll ...

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Property Type

Islamorada Condo

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Islamorada Cottage
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

$1286

avg/night

$1,286
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

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

Featured review

"Osprey Bay January"

Just finished a week at Osprey Bay nice house a little too much up and down with all the steps but spacious Need a larger trash can in the kitchen put it next to the wall near toaster Also new pillows ...

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$167

avg/night

$167
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Popular Beacon Reef Condo Oceanfront Islamorada, Florida (Max 4 Persons / **MONTHLY RENTALS ONLY!!) Come and enjoy our Paradise Found 2nd home. FREE BOAT DOCKAGE (with proof of insurance) In the fishing capital of the world, Islamorada. If you have never experienced summer in the Keys, you might be surprised! ...

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Property Type

Islamorada Condo

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.9 miles to Founders Park

$109

avg/night

$109
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

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

Featured review

"Absolutely Beautiful"

We stayed at Sharon's place in Islamorada for 10 days and had an amazing time....it was the perfect size, very clean, and had everything we needed. It was so affordable, we even stayed the night in Key ...

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Islamorada House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$1786

avg/night

$1,786
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Introducing Maison Residences Unit 201, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean ...

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Property Type

Islamorada House

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Islamorada Villa
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$664

avg/night

$664
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Short DescriptionCommunity amenities: heated pool, boat dock, BBQ Walk to shops, grocery store, parks, restaurants ️ All bedrooms feature ensuite bathroom Dog friendly 24/7 Guest support teamIsla Acai (Villa #8) is part of Little Basin Villas upscale community of nine luxury vacation ...

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Property Type

Islamorada Villa

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 5 miles to Anne's Beach

$327

avg/night

$327
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Enjoy the sunrise from the balcony or from the condo through 50' of glass sliding doors. You can also view the sunset from our walkway on bayside. We have a full kitchen, dishwasher to microwave, washer/dryer, even beach towels. We have wifi,cable TV in living area and all bedrooms, master bath ...

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Property Type

Islamorada Condo

Featured review

"Keys Condo"

Awesome peaceful location,clean and perfect amenities lots of birds and fish at marina manatee, sand sharks ,etc

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Islamorada House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$520

avg/night

$520
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Escape to paradise and experience the ultimate vacation getaway at our stunning 4-bedroom, 3-bathroom canal home in the heart of Islamorada. Nestled along the crystal-clear waters of the Florida Keys, this exceptional rental offers a perfect blend of comfort, convenience, and natural beauty.Key Features:Spacious ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$375

avg/night

$375
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of ...

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Property Type

Islamorada House

Featured review

"The Florida Keys at its Best!"

We stayed here in the “Honu Hale” house in August 2024 during the Florida Lobster Season. The property is ideally laid out & set up for boaters, divers & fisherman. There’s plenty of dockage and a ...

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Islamorada House
8 BR | 9 BA | Sleeps 16 | Quick View
Sleeps 16, 8 bedrooms, 9 bathrooms

$2571

avg/night

$2,571
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Introducing Maison Residences Full floor for rent – Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —Units 201 and 202 rented together. Full floor… Private steps to pool, beach and Atlantic Ocean! 8 bedrooms, 8 full baths, 2 half baths, 2 full ...

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Property Type

Islamorada House

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Islamorada Condo
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

$563

avg/night

$563
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Sunrise is a spectacular unit within the Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach.Dockage can be obtainable through Islamorada ...

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Property Type

Islamorada Condo

Featured review

"Thrilled"

I was under contract on neighboring unit. I had absolute affirmation after staying one week in this unit.

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Islamorada House
6 BR | 6 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 6 bathrooms

$3924

avg/night

$3,924
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Tea Table Key Private Island Estate and Wedding Venue An extremely rare and stunning private island, accessible by car, Tea Table Key is a gated Caribbean Island located at Mile Marker 79.7 in Islamorada.Jutting into the blue-green waters of the Atlantic Ocean, Tea Table Key features a 2,000′ ...

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Property Type

Islamorada House

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Islamorada Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

MM 87.7 . 2 Bedroom & 2 Bath. Rented 28 days minimum Experience the epitome of oceanfront luxury in this exquisite paradise! Delight in fishing the pristine waters of the Keys with the convenience of your own 30ft slip in a secure marina. Unwind in the comfort of your spacious condo that boasts ...

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Property Type

Islamorada Condo

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Islamorada House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
17 reviews

$475

avg/night

$475
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

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

Featured review

"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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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
23 reviews

$174

avg/night

$174
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This 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, pickleball, heated pool, private beach, and dockage for ...

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Property Type

Islamorada Condo

Featured review

"Great Stay/Location"

Excellent stay. Owner is super nice and helpful. Great location, beautiful sunsets. Easy access to both the bay and the ocean. Place was very clean when we arrived. Would stay again.

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Islamorada House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$2143

avg/night

$2,143
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

$15,000-$17,500 WeeklyA world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just a short 90-minute ...

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Property Type

Islamorada House

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

$151

avg/night

$151
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Gorgeous updated 2 bedroom, 2 bathroom condo with large modern kitchen in an oceanfront gated building with oceanfront pool, fishing dock, gym, sauna, barbecue grills and so much more, and the best part is YOU'RE IN THE FLORIDA KEYS!

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Property Type

Islamorada Condo

Featured review

"Jan Feb 2023"

Great condo, pool, and neighbors. Highly recommend. The pool is heated. Ocean view is great. Community room. Has exercise room and sauna.

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$433

avg/night

$433
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Mile Marker 74 – Bayfront – Beachfront – Handicap Assessable – Dockage for 30′ boatThis amazing beachfront home is a must see! Located on one of the few white sand beaches in the Florida Keys, Gulfview is a private home located on Lower Matecumbe Key in Islamorada in ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 4 bathrooms

Distance to beach: 0.5 miles to ANNE'S BEACH

$425

avg/night

$425
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Located in the desirable Islamorada which is know as the “Sportfishing Capital of the World” and where you will find the most beautiful crystal clear waters. The house is just minutes from Channel 5 and Channel 2 which give you quick access to the best ocean and backcountry fishing. You are ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$1000

avg/night

$1,000
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Beautiful bayfront house, private pool and dock, right in Downtown Islamorada Relaxing is made easy at Coral Cove 8, moving from open, airy living spaces to your own private pool. Bright modern finishes meld with traditional Key West style, Coral Cove 8 offers island living in style. This retreat is ...

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Property Type

Islamorada House

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Islamorada House
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms

$667

avg/night

$667
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Mile Marker 77 – Oceanfront – Lower Matecumbe Key.Six bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade or sun on the private beach, ...

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Property Type

Islamorada House

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Islamorada House
4 BR | 2.5 BA | Sleeps 11 | Quick View
Sleeps 11, 4 bedrooms, 2.5 bathrooms
1 review

$501

avg/night

$501
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

This charming, island style beach house on Lower Matecumbe Key is the perfect spot for your next Florida Keys vacation. This home can sleep up to 11 guests, with 4 bedrooms and 2 1/2 baths. The main living space features a fully equipped kitchen and an open floor plan with vaulted ceilings, tons of natural ...

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Property Type

Islamorada House

Featured review

"Perfect Florida Keys Vacation Home"

We loved Harbor Hideaway for our month long getaway to Islamorada. The home is beautiful with gorgeous sunset views and huge private balconies. The newly renovated bathrooms are fantastic! The outdoor ...

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Islamorada House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$588

avg/night

$588
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Islamorada waterfront gem located on Sandy Cove Basin with total renovations completed in 2024. New pool and spa, new deep water dock. Three en suite king bedrooms. Nicely appointed kitchen. Private gated and fenced yard with ample parking.

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Property Type

Islamorada House

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Islamorada House
3 BR | 2.5 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2.5 bathrooms

$667

avg/night

$667
avg per night
View Details

Key Amenities

  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Traditional coastal cottage styling built in 2017 and the Pool was added in 2020. Large backyard beach and only steps to the turquoise waters of the Atlantic Ocean. Kayak, paddle board, or kite ski from your backyard! Plenty of parking out front and private gated access; fencing around the perimeter. ...

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Property Type

Islamorada House

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Islamorada House
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms
5 reviews

$667

avg/night

$667
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Deam home in they keys is a 4000 square foot home on water with heated/chilled Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large bedrooms and three baths. Equipped with four king beds, one ...

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Property Type

Islamorada House

Featured review

"Amazing home and amazing renter️"

This home is a literal dream for individuals wanting to enjoy the beautiful outdoors in Islamorada. The beds were super comfortable, and the kitchen was roomy and had everything we needed. The additional ...

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Islamorada House
1 BR | 1.5 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1.5 bathrooms

$265

avg/night

$265
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Sunshine Place 84371 Overseas Highway, Islamorada, FLLOCATION: Oceanside HouseMINIMUM STAY: WeeklyMILE MARKER: 84.3DETAILS: "Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing ...

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Property Type

Islamorada House

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founders Park

$219

avg/night

$219
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condominium (CHC) . Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally decorated in Tropical Modern style. A 30' Boat Slip ...

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Property Type

Islamorada Condo

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Islamorada House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to beach: 0.5 miles to White Marlin Beach

$350

avg/night

$350
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

*******Check us out on VRBO No. 2003434******** Please go to ....**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 ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 50 yards to White Marlin

$295

avg/night

$295
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Located across from White Marlin beach This canal home has protected deepwater dockage , on the most sought-after street, on Gulfview Drive in Islamorada. Enjoy sunset and bay views from White Marlin Beach. Gulfview, known as the 'sugar sand beach', offers 3 bedrooms, 2 bathrooms, dining, ...

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Property Type

Islamorada House

Featured review

"Clean and comfortable in a great location"

The home is very comfortable with three bedrooms and a spacious living/dining area. The master bedroom is a bit cozy and lacks a closet, but the two bedrooms that share the Jack-and-Jill bathroom have ...

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Islamorada House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
4 reviews

$614

avg/night

$614
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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

Featured review

"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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Islamorada Townhome
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms

$126

avg/night

$126
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Fully furnished 2 bedroom 1. 1/2 baths with balcony, heated pool, sauna and fitness room. Also a community room with flat screen and full kitchen, pool and ping pong. Beautiful ocean view from pool and community room. Huge ocean front dock for fishing, snorkeling and kayaking. WiFi , restaurants ...

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Property Type

Islamorada Townhome

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Islamorada House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 3 bathrooms

$643

avg/night

$643
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Martin Family Fish Camp 106 Madeira Rd., Islamorada, FloridaLOCATION: 2 Houses Located on a private peninsulaMINIMUM STAY: WeeklyMILE MARKER: 81.9DETAILS: The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each ...

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Property Type

Islamorada House

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$195

avg/night

$195
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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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Islamorada House
5 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 5 bathrooms
3 reviews

$1400

avg/night

$1,400
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Oceanfront Estate on 3.5 PRIVATE Acres in the Heart Of Islamorada. Features include: Private Boat Basin with 100 of feet of dockage for any size boat, private boat ramp and fishing pier. HUGE salt pool and hot tub, 3rd floor private master suite w/ office, master bathroom and private balcony. This huge ...

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Property Type

Islamorada House

Featured review

"Best vacation ever"

I can’t express enough how our month in this house was above expectations. It was my retirement party and over the month had friends, family and high school buddies. The house was huge and 5 couples were ...

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Islamorada House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 3 bathrooms
3 reviews

$525

avg/night

$525
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

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

Featured review

"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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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$217

avg/night

$217
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner

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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Islamorada Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$183

avg/night

$183
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...

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Property Type

Islamorada Apartment

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Islamorada Cottage
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$290

avg/night

$290
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

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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Islamorada Condo
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms

Distance to beach: 4 miles to Founders Park

$290

avg/night

$290
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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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Islamorada House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$588

avg/night

$588
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

PROPERTY NAME: Pirate's Paradise 84745 Old Highway Unit A2, Islamorada, FloridaLOCATION: Oceanview home located in an oceanfront Islamorada community, only 90 minutes from Miami!MINIMUM STAY: 7 days MILE MARKER: 84DETAILS: Pirate's Paradise at Peaceful Palms: The Ultimate Oceanview ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

$291

avg/night

$291
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Great house! Great location!HOUSE ON CANAL… 34 foot concrete dock with fish cleaning stand, water and electricity. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. We are also ...

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Property Type

Islamorada House

Featured review

"Absolutely Perfect!"

The house was absolutely beautiful and perfect for bringing your boat. We had four adults and a one year old and the spacious home comfortably and easily accommodated us. Simple and easy access to Snake ...

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$137

avg/night

$137
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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

Featured review

"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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Islamorada Villa
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms
2 reviews

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 Bed & 2.5 Bath Villa in Anglers Reef with Boat slip.Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious ...

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Property Type

Islamorada Villa

Featured review

"Great accomodations"

Beautifully decorated house in the Keys. Very spacious and comfortable. Kitchen was fully stocked. Plenty of linens and extra towels. The community dock has kayaks we used. There are lobsters under ...

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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 110 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 $87 per night with an average price per night of $379.

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 49 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 47 oceanfront rentals in Islamorada available on FloridaRentals.com. Use our filters to search and book yours today!