Islamorada Beachfront Rentals

(40 rentals)
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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the 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 Condo

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Islamorada House | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
7 reviews

$957

avg/night

$957
avg per night
View Details

Key Amenities

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

About this property

‘The Beach House’ at Tarpon Point in Islamorada- DIRECT RENTAL WITH NO ADMIN OR CC FEESDo not be deceived by other units' lower "nightly rates"; we are the largest/most private unit and have the lowest total rental cost! Why pay more for less?‘The Beach House’ ...

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Property Type

Islamorada House

Featured review

"Very peaceful and beautiful accommodations"

Impressive location. View from master bedroom is fantastic. House was clean, comfortable, well furnished and great layout. Area is easy to navigate and lots of great restaurants close bye. Green Turtle ...

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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review
owner special
Owner special: 15% off Jan1 through Feb 4 2024. I rent from Saturday to Saturday so take 1 2 3 or 4 weeks Remodeled

$322

avg/night

$322
avg per night
Owner special:
15% off Jan1 through Feb 4 2024. I rent from Saturday to Saturday so take 1 2 3 or 4 weeks Remodeled

View Details

Key Amenities

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

About this property

We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you ...

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Property Type

Islamorada Condo

Featured review

"Outstanding view and amenities. Will return soon!"

Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.

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

$946

avg/night

$946
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

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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Islamorada House | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

$1346

avg/night

$1,346
avg per night
View Details

Key Amenities

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

About this property

Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experience for those looking for a luxurious and private getaway. Each spacious bedroom and en suite bathroom is inspired by modern coastal furnishings. Perfect for entertaining family and friends, ...

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Property Type

Islamorada House

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Islamorada House | On the beach
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

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

$658

avg/night

$658
avg per night
View Details

Key Amenities

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

About this property

SAVE VRBO's $500-600 Booking fee!!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 ...

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Property Type

Islamorada House

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Islamorada Apartment | On the beach
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
46 reviews

$174

avg/night

$174
avg per night
View Details

Key Amenities

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

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

Featured review

"Slice of Paradise"

We’ve been coming to the Keys for 20 years and this place takes the win. Jerry and Lisa are so friendly and make you feel very welcome and comfortable. The apartment has everything you need including ...

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Islamorada House | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
9 reviews
owner special
Owner special: Available starting January 6Looks better in person than pictures!

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

$643
avg per night
Owner special:
Available starting January 6Looks better in person than pictures!

View Details

Key Amenities

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

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

Featured review

"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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Islamorada House | On the beach
5 BR | 5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5 bathrooms

$820

avg/night

$820
avg per night
View Details

Key Amenities

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

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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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 100 feet to Front door

$231

avg/night

$231
avg per night
View Details

Key Amenities

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

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

Featured review

"Ocean Harbor M3 is Fabulous!"

Priceless view of the ocean. Nice marina. Workout room is great with a view. The condo is clean and spacious. Every thing you need is here. Very easy to maintain. During my 3 month stay from May to August ...

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Islamorada House | On the beach
6 BR | 7.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 7.5 bathrooms

Distance to beach: 1 feet to on property or at Founders Park

$371

avg/night

$371
avg per night
View Details

Key Amenities

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

About this property

Beautiful new home on Florida Bay with sandy beach, spacious pool, beautiful views, and sunsets every night. Three Private Suites are offered to accommodate up to 12 guests. Each suite can be rented individually or combined. I would be happy to discuss your needs and answer any questions you may have. ...

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Property Type

Islamorada House

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

$214

avg/night

$214
avg per night
View Details

Key Amenities

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

About this property

This condo is located in one of Islamorada's most prestigious condo complexes.PROPERTY NAME: Beacon Reef #407 83201 Old Highway, Islamorada, FloridaLOCATION: Ocean side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 83.2DETAILS: ...

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Property Type

Islamorada Condo

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Islamorada House | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1375

avg/night

$1,375
avg per night
View Details

Key Amenities

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

About this property

Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends. ...

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Property Type

Islamorada House

Featured review

"Beautiful stay"

We had the best time at this house! Giovanna and her husband were wonderful hosts and were on top of everything we needed. The house itself is in a great location close to shops and restaurants. Book the ...

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Islamorada House | On the beach
3 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3.5 bathrooms
24 reviews

$1363

avg/night

$1,363
avg per night
View Details

Key Amenities

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

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 a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler.You will escape ...

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Property Type

Islamorada House

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Islamorada House | On the beach
9 BR | 8 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 8 bathrooms

$1781

avg/night

$1,781
avg per night
View Details

Key Amenities

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

About this property

Welcome to Infinity Bay Islamorada, an infinite paradise with infinite possibilities in the heart of the Florida Keys. This exclusive property offers a blend of sophistication and tranquility, where guests can unwind in style against the backdrop of crystal-clear turquoise waters and swaying palm trees. ...

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Property Type

Islamorada House

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Islamorada House | On the beach
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5 bathrooms

$5486

avg/night

$5,486
avg per night
View Details

Key Amenities

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

About this property

Welcome to Caribee Beach House!Discover the enchanting charm of Caribee Beach House, where the timeless allure of old-school Islamorada beautifully melds with stylish comforts. Tucked away in the heart of downtown Islamorada, this hidden gem offers an extraordinary retreat with 200 feet of private ...

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Property Type

Islamorada House

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Islamorada Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

$218

avg/night

$218
avg per night
View Details

Key Amenities

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

About this property

This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers ...

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Property Type

Islamorada Condo

Featured review

"Location"

We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.

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Islamorada Townhome | On the beach
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms
2 reviews

$359

avg/night

$359
avg per night
View Details

Key Amenities

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

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

Featured review

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

$491

avg/night

$491
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 | On the beach
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 Villa | On the beach
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 Condo | On the beach
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 Condo | On the beach
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$681

avg/night

$681
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

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

$3970

avg/night

$3,970
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 House | On the beach
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 | On the beach
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 House | On the beach
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 Cottage | On the beach
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 House | On the beach
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$2435

avg/night

$2,435
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 | On the beach
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 House | On the beach
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 House | On the beach
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 | On the beach
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms
2 reviews

$400

avg/night

$400
avg per night
View Details

Key Amenities

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

About this property

Anglers Reef Villa Resort 2 Bedroom and 2.5 Bath Villa, in Anglers Reef with Boat Slip. An 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 ...

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Property Type

Islamorada House

Featured review

"Awesome home"

Amazing home and location. Great customer support. Would love to return to here again. Islamorada is so beautiful

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

$1013

avg/night

$1,013
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 | On the beach
5 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 5 bathrooms
3 reviews

$1400

avg/night

$1,400
avg per night
View Details

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 Townhome | On the beach
2 BR | 3 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 3 bathrooms

$175

avg/night

$175
avg per night
View Details

Key Amenities

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

About this property

Enjoy breathtaking sunsets on the private beach while staying in this beautifully remodeled corner unit. The unit was completely gutted in 2021 and features 2 bedrooms plus a built out loft and 3 full bathrooms.The unit has a huge master with a king bed plus a bathroom/walk-in closet and ...

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Property Type

Islamorada Townhome

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Islamorada Estate | On the beach
5 BR | 3.5 BA | Sleeps 17 | Quick View
Sleeps 17, 5 bedrooms, 3.5 bathrooms
2 reviews

$2496

avg/night

$2,496
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Islamorada Estate

Featured review

"Milestones Birthday Celebration /Family Vacation"

Absolutely beautiful home..Featured everything we needed to enjoy our vacation..Spacious enough for 14 people. Close to places if we decided to go out n explore..Epic week.!!Thank you

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Islamorada House | On the beach
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$667

avg/night

$667
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Seeing is believing. The Captain's Quarters is a direct, oceanfront home on the Atlantic shoreline of Islamorada. For your planned getaway, come enjoy truly private and relaxing oceanfront living in the heart of Islamorada, in a unique home boasting a treasure-trove of Florida Keys history. The ...

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Property Type

Islamorada House

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Islamorada Apartment | On the beach
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 Villa | On the beach
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