New Property Coming Soon! $25,000-$27,000 Monthly

New Property Coming Soon!

$25,000-$27,000 Monthly

Interior photos coming soon

4 beds 2 baths

Blue Oasis Estate $12,500 Weekly - Call for holiday rates

Blue Oasis Estate

$12,500 Weekly - Call for holiday rates

Mile Marker 81 – Oceanfront Welcome to your exclusive oceanfront oasis in Islamorada, in the Florida Keys! This 3-bedroom, 3-bath rental estate is a haven of luxury, featuring panoramic views of the Atlantic including Alligator Light, a private pool, and access to over 250′ of…

3 beds 3 baths

Key Largo Ocean Resort 276 $7,500 Monthly * Discount

Key Largo Ocean Resort 276

$7,500 Monthly * Discount

Escape to Paradise in Key Largo: Your Dream Vacation Awaits! Mile Marek 94.8 Welcome to your slice of paradise in Key Largo! This stunning 4-bedroom, 3.5-bath home is the perfect vacation rental for those seeking a luxurious and relaxing getaway. With a resort-style pool, this…

4 beds 3.5 baths

Contact for more details, Located at mile market 81 and convenient to all properties!  305-664-3333   $900 a week for boats up to 27 feet. $1,400 a week  for boats up to 40 feet. Must arrange ahead of arrival and fill out paperwork.

Sunrise Lookout $10,000 / monthly

Sunrise Lookout

$10,000 / monthly

Mile Marker 82 – Open Ocean front *Upstairs only for rent, Sunrise Lookout looks out on the world famous blue green waters of the Florida Keys.  Spend every morning greeted by a beautiful sunset, and every evening enjoying cool ocean breezes.   Up the stairs, the…

2 beds 1 bath

Happy Ours $30,000 / monthly

Happy Ours

$30,000 / monthly

Mile Marker 74.5 – Open Bayfront Six Bedroom/ Six Bath Ultra-Luxurious, Open water front estate with more than 5,000 square feet under air and 4,500 of covered terraces and deck.  Walk out the back door to the world famous Port Antigua gated community beach!  The…

6 beds 6 baths
Maison Residences offers world-class oceanfront residences in the Florida Keys. Unit 102 at Maison Residences is a luxurious property offering sweeping views of the Atlantic Ocean from the kitchen, grand room, master bedroom, and oversized living terraces. The residence is clean, stylish, and offers all...
4 beds 4.5 baths

Venetian Villa – Brand New $25,000 / monthly

Venetian Villa – Brand New

$25,000 / monthly

Mile Marker 74 – Bayfront observation pier / Boat basin dockage 5 bedroom and 5.5 bath with Pool and Dockage surrounded by natural beauty. The sparkling pool features a spa and waterfall overlooking the deep-water natural beauty and secluded portion basin and canal..  Just a…

5 beds 5.5 baths

Tea Table Key Private Island Estate and Wedding Venue $25,000 - $35,000 Weekly, Call for Holiday Wedding and event fees

Tea Table Key Private Island Estate and Wedding Venue

$25,000 - $35,000 Weekly, Call for Holiday Wedding and event fees

Mile Marker 83 – Oceanfront

Two 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 observing pier.  Relax at the beach or cool down in the beachside pool.

The front home sits waterfront with 1 bedroom 1 bath upstairs, and a separate 1 bedroom 1 bath downstairs.  Downstairs is great for entertaining with a pool table, wet bar, poker table and more.

The garden cottage sits back on the property with two bedrooms and one bathroom and is just a walk through the sandy garden away from the ocean front house.

The ocean front paradise is also a ‘Destination/Wedding Location!’

$9,000/week –  Call for Holiday Rates.

The viewing dock is just that, it is too shallow for boats so boats are prohibited. But great for light flats fishing, catch small flats fish or pitch a kayak out. We do have information on nearby marinas for dockage.

Please note, the Pool is heated to 88 degrees and does NOT have a hot tub.   The side pool is a spa with jets.

[vc_video link='https://www.youtube.com/watch?v=o0jYKUSoVlY']

Oceanfront Beach Cottages

6 beds 5 baths

Maison Residences – Unit 402 – Oceanfront & Pool Front $7.5k Weekly, $25k Month - call for holiday rates

Maison Residences – Unit 402 – Oceanfront & Pool Front

$7.5k Weekly, $25k Month - call for holiday rates
Introducing Maison Residences 402... Planning a vacation to the Florida Keys? Consider a stay in Islamorada, a village comprised of six of the Florida Keys, located halfway between Key West and Miami. Islamorada is known for its coral reefs, rich history, and lavish accommodations. Where...
3 beds 3.5 baths

Sea Breeze Villa $12,000 Monthly, call for off season

Sea Breeze Villa

$12,000 Monthly, call for off season

Mile Marker 81 – Heart of Islamorada

A magical, modern, Island-style Villa with the ideal location!  This newly renovated Villa, in Green Turtle Beach Neighborhood, features 2 bedrooms, 2.5 baths, and a custom pool featuring a private sandy area around pool.

3 beds 3 baths

Blue Heaven Bahamas $7,000 Call for Holiday Rates

Blue Heaven Bahamas

$7,000 Call for Holiday Rates

Truly Heaven

5/5 Stars Stayed Mar 2019

Melanie W. • St Louis

Blue Heaven was a perfect home away from home for our family of 5. The living spaces were so comfortable, well-appointed, and well-supplied. The location – steps from the waves and also a short walk to town and harbor – was ideal. We couldn’t have been happier!

3 beds 3 baths

Nautica $20,000 / monthly

Nautica

$20,000 / monthly

Mile Marker 83 – Bayfront Welcome 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.  …

4 beds 4 baths

Seaside Breezes $18,000-$20,000 Monthly

Seaside Breezes

$18,000-$20,000 Monthly

Mile Marker 94. Three bedrooms/two baths.   Ocean front in South Key Largo– this private gated home has dockage and is known for the soft breezes & beautiful sunrises.   Enjoy the Atlantic Ocean how a local enjoys it… Enjoy mornings on the wrap around patio watching…

3 beds 2 baths

Ocean Terrace Currently Under Construction

Ocean Terrace

Currently Under Construction

Mile Marker 81.5, This 3 bedroom, 3 bath home is complete with den, breezes and sunrises.   Featuring a jacuzzi and splash pool located right next to the sandy beach, this home comfortable sleeps 6-8 people. Currently Under Construction Vacation Rental License #VR-047.  

3 beds 3 baths

The Beach House $10,000 Weekly - Call for holiday rates

The Beach House

$10,000 Weekly - Call for holiday rates

Mile Marker 80 – Oceanfront Indulge in the island lifestyle at this beautiful private estate located in the heart of Islamorada. The gated property is lush in tropical landscaping that boost an oceanfront pool, boat dockage, brand NEW tennis court and sand volleyball net. Enjoy…

4 beds 4 baths

Sea Ranch $9,000 weekly ~ Call for holiday rates

Sea Ranch

$9,000 weekly ~ Call for holiday rates

Mile Marker 83 – Oceanfront

Two 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 observing pier.  Relax at the beach or cool down in the beachside pool.

The front home sits waterfront with 1 bedroom 1 bath upstairs, and a separate 1 bedroom 1 bath downstairs.  Downstairs is great for entertaining with a pool table, wet bar, poker table and more.

The garden cottage sits back on the property with two bedrooms and one bathroom and is just a walk through the sandy garden away from the ocean front house.

The ocean front paradise is also a ‘Destination/Wedding Location!’

$9,000/week –  Call for Holiday Rates.

The viewing dock is just that, it is too shallow for boats so boats are prohibited. But great for light flats fishing, catch small flats fish or pitch a kayak out. We do have information on nearby marinas for dockage.

Please note, the Pool is heated to 88 degrees and does NOT have a hot tub.   The side pool is a spa with jets.

[vc_video link='https://www.youtube.com/watch?v=o0jYKUSoVlY']

Oceanfront Beach Cottages

4 beds 3 baths

Green Turtle Beach $13,500 -$15,000, Call for Holiday Rates

Green Turtle Beach

$13,500 -$15,000, Call for Holiday Rates

Mile Marker 81. Ocean front estate with five bedrooms, five & a half baths.   One of the most ultra-luxurious properties in Islamorada, Green Turtle Beach features an immaculately manicured 4 acres of ocean front land.   Catch ocean breezes off the multiple porches and balconies at…

5 beds 5.5 baths

Gulfview $13,000-$15,000 Monthly Call for holiday rates

Gulfview

$13,000-$15,000 Monthly Call for holiday rates

The private home features 3 modern bedrooms and 2 updated baths and sleeps 6 adults.  The master bedroom features a king size bed and stunning bay and sunset views.  Two guest bedrooms, one with a king bed and one with a queen bed makes this house ideal for friends or family.  An additional bunk room with a bunk and day bed provides plenty of room for accompanying children.  

3 beds 2 baths

Little Bay $3,000 weekly/unit

Little Bay

$3,000 weekly/unit

Mile Marker 82 – Bayfront Multiple units available, including the Duplex (up and downstairs).  Located bayside, Little Bay has some of the best sunsets in Islamorada.   Great dockage, wildlife, and snorkeling makes this property even more beautiful. Each unit has 2 bedrooms, 1.5 bath, sleeps…

2 beds 2 baths

Oasis At Tavernier $20,000 Monthly ~ Call for Holiday Rates

Oasis At Tavernier

$20,000 Monthly ~ Call for Holiday Rates

$20,000 monthly~ Call for holiday rates   Mile Marker 92.   This luxurious 6 bedroom estate is located in Tavernier, in the Upper Florida Keys. Conveniently located a short distance from the Atlantic Ocean, deep water dockage makes Oasis in Tavernier perfect for boaters.  …

6 beds 7 baths

Little Bay Cottage $3,000 weekly

Little Bay Cottage

$3,000 weekly

Mile Marker 82 – Bayside One bedroom/two bath with Florida room. Newly remodeled. Vacation Rental License #VR-086.  

1 bed 2 baths

Ocean Harbor w/ Dockage $7,500 Monthly Call for holiday rates

Ocean Harbor w/ Dockage

$7,500 Monthly Call for holiday rates

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…

2 beds 2 baths

Key Largo Ocean Resort 248 $15,000 Monthly

Key Largo Ocean Resort 248

$15,000 Monthly

Escape to Paradise in Key Largo: Your Dream Vacation Awaits! Mile Marker 94.8 Welcome to your slice of paradise in Key Largo! This stunning 4-bedroom, 3.5-bath home is the perfect vacation rental for those seeking a luxurious and relaxing getaway. With a resort-style pool, this…

4 beds 3.5 baths

Ishmael’s Watch $20,000 / Monthly Call for Holiday rates

Ishmael’s Watch

$20,000 / Monthly Call for Holiday rates

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…

6 beds 4 baths

Conch Villa @ Little Basin Villa $4,360 - $6,000 Weekly, Call for holidays

Conch Villa @ Little Basin Villa

$4,360 - $6,000 Weekly, Call for holidays

3 Bedrooms & 3.5 bathrooms Villa 6 $4,360 – $6,000 Weekly depending on dates Mile Marker 81.6 — Conch Villa Conch Villa, aptly named for the famous large snails that inspired the Keys to be called the ‘Conch Republic,’ is located in the heart of…

3 beds 3.5 baths

Osprey Bay $8,000-9,000Weekly

Osprey Bay

$8,000-9,000Weekly

Mile Marker 82.7 – Bayfront A quaint 5 bedroom home bay-front with some of the best sunsets in the Florida Keys!  Fully equipped home with heated pool, dockage, and large spacious living quarters.  Located in heart of Islamorada. 5 bedrooms, 3 baths, sleeps 10-12, dockage,…

5 beds 3 baths

Key Lime Villa $4,000 - $6,000 Weekly depending on dates

Key Lime Villa

$4,000 - $6,000 Weekly depending on dates

3 Bedrooms & 3.5 bathrooms Villa 2 $4,000 – $6,000 Weekly depending on dates Mile Marker 81.6 — Key Lime Villa   Key Lime Villa, aptly named for the famous Key’s citrus fruit, is a new construction Villa located in the heart of Islamorada. The…

3 beds 3.5 baths

Sunrise – Maison Matecumbe $5,000/ weekly - Call for holiday rates

Sunrise – Maison Matecumbe

$5,000/ weekly - Call for holiday rates

Welcome to your dream vacation home in Islamorada, the jewel of the Florida Keys! This 3-bedroom condo boasts a prime location, with breathtaking views of the crystal-clear pool, Atlantic Ocean, and glistening white sand beach. As soon as you step inside, you’ll be enchanted by…

3 beds 3 baths

Maison Residences – Unit 101 – Beachfront $12,000-$14,000 - Discounted Summer rates available

Maison Residences – Unit 101 – Beachfront

$12,000-$14,000 - Discounted Summer rates available
Introducing Maison Residences 101... Islamorada, also known as “Village of Islands” or the “Fishing Capital of the World,” is a village of six islands located approximately 90 minutes south of Miami. The popular vacation destination boasts a wide range of activities, from the Theater of...
4 beds 4.5 baths

Maison Residences – Unit 204 – Oceanfront Price is in Property Description

Maison Residences – Unit 204 – Oceanfront

Price is in Property Description

$8-12,500 WEEKLY FALL SEASON $16,000 WEEKLY RENTAL SEASON Please call for holiday rates   Introducing Maison Residences Unit 204, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE — A world-class oceanfront residence, located in the heart of Islamorada in the Florida…

4 beds 4.5 baths

Maison Residences – Unit 203 – Oceanfront $8-10,000 WEEKLY $12,500 WEEKLY RENTAL SEASON

Maison Residences – Unit 203 – Oceanfront

$8-10,000 WEEKLY $12,500 WEEKLY RENTAL SEASON
$8-10,000 WEEKLY FALL SEASON $12,500 WEEKLY RENTAL SEASON Please call for holiday rates Introducing Maison Residences 203... Nestled between the turquoise waters of the Florida Strait and the wilderness of Everglades National Park is Islamorada. The quaint village of Islamorada is made up of six...
4 beds 4.5 baths

Maison Residences – Unit 202 – Oceanfront Price is in Property Description

Maison Residences – Unit 202 – Oceanfront

Price is in Property Description
$10-12,500 WEEKLY FALL SEASON $15,000 WEEKLY RENTAL SEASON Please call for holiday rates UP TO 32’ BOAT SLIP MAY BE AVAILABLE Introducing Maison Residences 202... There’s nothing quite like vacationing in the Florida Keys. The warm weather, sunny skies, and tropical environment create the ultimate...
4 beds 4.5 baths

Maison Residences – Unit 201 – Oceanfront Price is in Property Description

Maison Residences – Unit 201 – Oceanfront

Price is in Property Description

$8-12,500 WEEKLY FALL SEASON $16,000 WEEKLY RENTAL SEASON Please call for holiday rates   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…

4 beds 4.5 baths

Seagrape Cottage $7,500 / Month

Seagrape Cottage

$7,500 / Month

MM 81 – Heart of Islamorada 2 bedroom & 2 bath, set in the heart of Islamorada, near restaurants and shopping, great location for walking/biking to cultural areas! Newly renovated and now with a newly installed POOL! ***Optional Add on Dockage available at weekly rates,…

2 beds 2 baths

Paradise Found- w/ neighborhood beach! $18,000 / Monthly *$15,000 Summer Special*

Paradise Found- w/ neighborhood beach!

$18,000 / Monthly *$15,000 Summer Special*

Mile Marker 75 – Bayside 🏖️ Luxurious 4 Bedroom, 4 Bath Vacation Rental Home with Dockage and Beach Access in Islamorada, Florida Keys 🏖️ Nestled in the heart of the enchanting Islamorada, known as the “Village of Islands,” this exquisite 4-bedroom, 4-bath vacation rental home…

4 beds 4 baths

Kahiki Creek $20,000 / Monthly Call for holidays

Kahiki Creek

$20,000 / Monthly Call for holidays

🌴 Kahiki Creek – Tropical Paradise Getaway in Islamorada, Florida Keys 🌴 Welcome to the exquisite rental home nestled on a quiet natural canal in Islamorada… A picturesque oasis in the enchanting Florida Keys. Immerse yourself in the ultimate blend of luxury, comfort, and stunning…

4 beds 3 baths

Tropical Villa $19,000 / Monthly

Tropical Villa

$19,000 / Monthly

Mile Marker 77 – Waterway – Ocean side Immaculately designed and landscaped home with heated pool and dockage located in a quiet neighborhood in Lower Matecumbe Key.  Built in 2019, the 2900 sq. ft. home features a large, covered outdoor kitchen, pool area, dockage and…

4 beds 3.5 baths

Madeira Villa $20,000 / Monthly

Madeira Villa

$20,000 / Monthly

Fantastic for entertaining, Madeira Villa features a large and partially covered pool and deck area with plenty of activities for entertaining guests!  Multiple decks and patios overlook a heated pool and dockage on a canal with easy access to the world famous Florida Keys waters. …

3 beds 2 baths

Bella Del Mar $12,000 - $15,000 / Monthly

Bella Del Mar

$12,000 - $15,000 / Monthly

3 bedroom, 3 bath home on an immaculately updated and maintained canal front home in  the famous Port Antigua neighborhood, Islamorada, Florida Keys. Excellent dockage and access to Port Antigua Beach, one of the best white sand beaches in the Florida Keys. Inside the home,…

3 beds 3 baths

Palm Cottage South $15,000 / Monthly

Palm Cottage South

$15,000 / Monthly

Mile Marker 75 – Bayside 4 bedroom 3 bath   Palm 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…

4 beds 3 baths

Sweet Escape $20,000 - $24,000 / Monthly

Sweet Escape

$20,000 - $24,000 / Monthly

Sweet Escape is an exquisite, canal front home located in Islamorada in the Florida Keys. This impeccable 5 bedroom villa benefits from having wide, clear dockage in front of the house, a secluded pool & tiki area, and access to the famous and gated Port…

5 beds 5 baths

Latitudes $20,000 - $25,000 / Monthly

Latitudes

$20,000 - $25,000 / Monthly

Mile Marker 75 – Bayside Large, 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,…

4 beds 2.5 baths

Holly’s Hideout $12,500 / Month

Holly’s Hideout

$12,500 / Month

Mile Marker 91 – Ocean Side Situated on a clean, clear canal with deep water access to either the bay or ocean via Tavernier Creek! Enjoy your island time in this bright and breezy hideaway … Two bedrooms/Two baths upstairs along with open living, dining…

4 beds 3 baths

Morada Breeze in Venetian Shores $6,900 - $8,000 / Month

Morada Breeze in Venetian Shores

$6,900 - $8,000 / Month

Located in Venetian shores, this lower level 2 bedroom unit is complete with pool and dockage.   Dockage has great access to Ocean via Snake Creek where you’ll find the blue green water and the fishing that made Islamorada famous.  The upstairs will not be occupied during…

2 beds 1 bath

Seas the Day $11,000-$13,000 Monthly, Call for Holiday rates

Seas the Day

$11,000-$13,000 Monthly, Call for Holiday rates

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…

4 beds 4 baths

Barefoot Elegance $27,500 / monthly

Barefoot Elegance

$27,500 / monthly

Mile Marker 75, 5 bedrooms, 4 baths, sleeps 10, luxurious, heated pool, deep water dockage. Boathouse with slip.  

5 beds 4 baths