Luxury Vacation Rentals in Islamorada

(67 rentals)
booking message booking message

Key Amenities

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

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 ...

View all property information

Property Type

Islamorada House

"WOW is all we can say!!! Amazing rental."

We have been renting in the Keys for 22 years, this one topped them all. The grounds are SO secluded and private, makes you feel like your staying in the Jungle. Peacocks, exotic birds, and cool lizards ...

See all reviews

Show less

4 BR | 4.5 BA | Sleeps 8 | Quick View

4
Owner special: LAST MINUTE SPECIAL! December 10-17 now only $751/nt all in!

$888

avg/night

View Details

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 ...

View all property information

Property Type

Islamorada House

"The Perfect Spot!"

We couldn't have asked for a better place to stay while visiting Islamorada. The Beach House was very well appointed and comfortable for our party of 8; lots of room to spread out, and yet plenty of seating ...

See all reviews

Show less

3 BR | 3 BA | Sleeps 6 | Quick View

$857

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

About this property

MM 81.5.  BRAND NEW construction located in the Heart of Islamorada!  Coral Cove is a gated, secluded and intimate community of 8 homes on the Florida Bay.   Featuring both a private pool in the back, and a community pool on the bay, Coral Cove also features 3.5 bedrooms, 3.5 baths, bay ...

View all property information

Property Type

Islamorada House

Show less

4 BR | 4 BA | Sleeps 8 | Quick View

$833

avg/night

View Details

Key Amenities

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

About this property

Mile Marker 73 – Bayfront observation pier / Boat basin dockage Four bedroom/ four bath home located on a bay front parcel with fantastic protected boat basin dockage. Best of both worlds! Dock multiple boats in your protected boat basin steps from the villa, or walk the grounds the the best sunset ...

View all property information

Property Type

Islamorada Villa

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

A new, private community of 8 upscale homes called Coral Cove is located equidistant between Lorelei's and Chef Michael for easy walking to everything in downtown Islamorada, hence the name.....Heart of Morada! The reviews speak for themselves.Enjoy your private dunk pool or sit around it having drinks ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

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

About this property

Explore this sunset heaven from our new bay deck where you can soak in the sun and get lost in our unique sunsets. Listen to the breeze while you sip your wine or go on a sunset cruise while you are in our island. Island Villa 1 is the place to be. It will entice you with all its amenities inside and ...

View all property information

Property Type

Islamorada Villa

"Great Vaca home!!"

Great vacation with our family! Very accommodating home owner with great communication! LOCATION,LOCATION,LOCATION.. I spend multiple weeks a year in Islamorada, and this gated community of 8 homes was ...

See all reviews

Show less

5 BR | 5 BA | Sleeps 10 | Quick View

$800

avg/night

View Details

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 ...

View all property information

Property Type

Islamorada House

Show less

4 BR | 2.5 BA | Sleeps 8 | Quick View

$800

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

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 ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

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

About this property

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and ...

View all property information

Property Type

Islamorada House

Show less

7 BR | 4 BA | Sleeps 14 | Quick View

$733

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

About this property

Mile Marker 77 – Oceanfront – Lower Matecumbe Key. Seven 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, ...

View all property information

Property Type

Islamorada Estate

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

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 ...

View all property information

Property Type

Islamorada Condo

Show less

4 BR | 4 BA | Sleeps 8 | Quick View

$700

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Facing due west this property takes full advantage of the spectacular sunset view over the bay. GreenFlash has a bayside infinity pool and dockage to help you take full advantage of the myriad of water activities available in Islamorada, the 'Sport Fishing Capital of the World.' The two story house has ...

View all property information

Property Type

Islamorada House

Show less

4 BR | 4.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.5 miles to White Marlin Beach

$692

avg/night

View Details

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 ...

View all property information

Property Type

Islamorada House

Show less

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 ...

View all property information

Property Type

Islamorada House

"Great place!"

Arlene was wonderful to work with. The home more than accommodated our mix of four couples. Thanks.

See all reviews

Show less

3 BR | 3 BA | Sleeps 8 | Quick View

$667

avg/night

View Details

Key Amenities

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

About this property

Wide ocean views from every room in this gated, monthly rented beachfront estate, aptly named ‘Southern Comfort’. Vacation comfortably in this 3 bedroom, 3.5 bath, immaculately kept home. Sprawling grounds on the 1/2 acre estate lead to a heated pool and over 80′ of private beach frontage. ...

View all property information

Property Type

Islamorada Villa

Show less

5 BR | 3 BA | Sleeps 12 | Quick View

1

$665

avg/night

View Details

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 ...

View all property information

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.

See all reviews

Show less

4 BR | 4 BA | Sleeps 10 | Quick View

3

Distance to beach: 2 miles to Founders Park

$652

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 ...

View all property information

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. ...

See all reviews

Show less

3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

avg/night

View Details

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 ...

View all property information

Property Type

Islamorada House

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to beach: 5 miles to Founder's

$643

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

MINIMUM STAY: 7 Nights SATURDAY TO SATURDAY The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each home offers two private bedrooms. Between the two homes the bedding is: King, Queen/Queen in Tarpon and Queen, Twin/Twin in Bonefish. ...

View all property information

Property Type

Islamorada House

"Awesome"

We stayed for a month at Blue Water Retreat and had an awesome time with family and friends. The ocean views were magnificent. The pool was a big hit with the kids. We even had our dog with us. Hope to ...

See all reviews

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

9
LAST MINUTE DEAL 11/29 - 12/26: Available now until Christmas any one week.

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

View Details

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. ...

View all property information

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 ...

See all reviews

Show less

DEAL

3 BR | 2.5 BA | Sleeps 8 | Quick View

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

$621

avg/night

View Details

Key Amenities

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

About this property

Vacation Rental License 097. Welcome to Anglers Reef, a very special community of vacation homes with UNOBSTRUCTED OCEAN VIEWS FROM EVERY ROOM!We are new to this site so no reviews yet, BUT MANY AT OUR DIRECT SITE (SEE "LINKS" TAB ON THE LEFT) AND 12 YEARS of top reviews ON VRBO PROPERTY ...

View all property information

Property Type

Islamorada Villa

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

SoFLA Vacations has just acquired 3 NEW UNITS in our inventory all with OPEN CALENDARS and ready for your WINTER 2023 STAY!!Enjoy these spacious, 2 & 3 bedroom townhomes at EXECUTIVE BAY in the heart of ISLAMORADA. Each unit features large living areas, gourmet kitchens, comfortable bedding, ...

View all property information

Property Type

Islamorada Townhome

"Amazing !"

We recently stayed at Beacon reef in January of 2022 .What a wonderful time we had! The condo was excellent, modern ,clean , just beautiful ! The grounds, immaculate .The exercize room was top notch.It ...

See all reviews

Show less

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 ...

View all property information

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. ...

See all reviews

Show less

Key Amenities

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

About this property

Beautiful three bedroom three bathroom oceanfront home with a one bedroom one bathroom guest cottage pool ,tiki hut, observation deck located in Islamorada. Has a big beach and the most amazing views. Home comes with full access to kayaks and Paddleboards. Plenty of parking… close to restaurants, ...

View all property information

Property Type

Islamorada House

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

1

$500

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool

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 ...

View all property information

Property Type

Islamorada Villa

"House was great with all the amenities!"

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

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool

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 ...

View all property information

Property Type

Islamorada House

Show less

$450

avg/night

View Details

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, ...

View all property information

Property Type

Islamorada House

"Waterfront Paradise"

This was a terrific location and home. The house and amenities were excellent. The backyard was the standout for our group with the pool, dock and Tiki area....this felt like a true resort get away. The ...

See all reviews

Show less

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. ...

View all property information

Property Type

Islamorada House

"A Dream Vacation Home!"

My family and I rented this home during the month of August. This perfect home has everything you need plus more! The home is newly built and maintained extremely well. Its location in Venetian Shores is ...

See all reviews

Show less

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 ...

View all property information

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 ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Founders

$429

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

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

View all property information

Property Type

Islamorada Apartment

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

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

View all property information

Property Type

Islamorada House

Show less

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Minimum Rental: 7 Days"Little Bay's Cottage" is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area ...

View all property information

Property Type

Islamorada Cottage

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

$425

avg/night

View Details

Key Amenities

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

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 ...

View all property information

Property Type

Islamorada House

Show less

2 BR | 2.5 BA | Sleeps 6 | Quick View

2

$400

avg/night

View Details

Key Amenities

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

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 ...

View all property information

Property Type

Islamorada Villa

"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 ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Minimum Rental: 28 nightsPelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. The main floor offers 3 bedrooms and an open concept with ample seating for the entire family. The large balcony overlooks a canal where pelicans are usually seen diving into ...

View all property information

Property Type

Islamorada House

Show less

5 BR | 3 BA | Sleeps 12 | Quick View

$400

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

MINIMUM STAY: 28 DAYS ONE OF A KIND!!! Magnificent two story townhouse with 5 bedrooms and 3 baths located on Lower Matecumbe in Islamorada. Sandglass is a four-unit condo complex located on Lower Matecumbe in Islamorada. This unit offers 180 degree ocean views and is situated on a large lagoon which ...

View all property information

Property Type

Islamorada Condo

Show less

Key Amenities

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

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 ...

View all property information

Property Type

Islamorada House

"Perfect Family Vacation Spot!"

We absolutely loved this charming community! It was the perfect place for our family to unwind after the unusual spring and summer! We rented a boat slip and it was an easy - peezy trip to the the sandbars ...

See all reviews

Show less

$399

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009 and 2022. Relax by the splash pool or sunbathe on the roof top and enjoy the spectacular views. There are blue water ...

View all property information

Property Type

Islamorada House

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 50 yards to White Marlin

$395

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

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 unobstructed sunset and bay views from White Marlin Beach. Gulfview, known as the 'sugar sand beach', offers 3 bedrooms, 2 bathrooms, dining, ...

View all property information

Property Type

Islamorada House

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

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

$390

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 ...

View all property information

Property Type

Islamorada House

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

1440 sf - Sleeps 6 (8 with the help of an EZ-Bed electric queen Bed/or large sectional couch with chaise lounge and cuddler). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community beach with beautiful sunsets. Well the ...

View all property information

Property Type

Islamorada House

"Location, location, location"

Wonderful location for a Keys vacation. Close to beautiful private beach and channel 2 and 5 bridges. Canal behind house makes it a perfect place if you have a boat (if not there are kayaks). House was ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

MINIMUM STAY: 28 NIGHTS Lyons Landing is an exceptional single family home with pool, dock, boat lift and outdoor living area located in the prestigious neighborhood of Venetian Shores in Islamorada. Everything you need for a spectacular vacation awaits you in this extraordinary home. 3 bedrooms ...

View all property information

Property Type

Islamorada House

Show less

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 ...

View all property information

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 ...

See all reviews

Show less

3 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to White Marlin Beach

$350

avg/night

View Details

Key Amenities

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

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 ...

View all property information

Property Type

Islamorada House

Show less

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 ...

View all property information

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 ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 1 miles to Anne's Beach State Park

$333

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This Condo sleeps 4 and comes with a 30' Boat slip, Tennis courts, pool, club house, undercover parking and elevators for easy access. Located on quiet Lower Matecumbe Key, Bay Harbour is just 7 miles from Islamorada's center with nearby beaches and parks. Newly refurnished and refurbished, this condo ...

View all property information

Property Type

Islamorada Condo

"Couldn't have picked a better place to kick off the new year!"

Great location with lots of fishing, great restaurants, beautiful sunsets and only 90 minutes to Key West. Highly recommend!

See all reviews

Show less

Key Amenities

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

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 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 has been remodeled, fully furnished, with a 90 ...

View all property information

Property Type

Islamorada House

"Little Piece of Paradise in Islamorada"

We stayed at Paradise during Feb and March 2022. Outstanding house on a canal 1 block from the Bay. House is well appointed and stocked with everything one needs to enjoy the Keys. Owners were wonderful ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Minimum Rental: 28 DaysHappy vacationing starts here! The owners call their special getaway “Bay Therapy” for many reasons. It is located in a great neighborhood in Key Largo. It is convenient to the mainland and is the gateway to the Keys. Since purchasing this home the owners have ...

View all property information

Property Type

Islamorada House

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

1

$319

avg/night

View Details

Key Amenities

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

About this property

Tropically furnished, privately owned condominium at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. Enjoy your morning coffee, watching the boats go out. Relax with an amazing sunset and a glass ...

View all property information

Property Type

Islamorada Condo

"Fantatic"

Fantastic host. fantastic location, fatastic accomodations! Looking forward to returning in 2022. Thank you Susan

See all reviews

Show less

Key Amenities

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

About this property

This home is located in the exclusive White Marlin Beach residences. Islamorada is one of the most eco diverse locations in the Florida Keys. The property is fully equipped for all your daily needs. There is 70ft of dock, which is available for use while renting. You will also have access to the private ...

View all property information

Property Type

Islamorada House

"Perfect Private Island Getaway...."

This is what we consider our paradise...This home was exceptionally clean, organized, and in a great location. It was everything we needed and expected. The sunrises and sunsets on the private beach were ...

See all reviews

Show less

Map
Expand map Close map
Islamorada Vacation Rentals