Happy Ours $30,000 / monthly
Happy Ours
$30,000 / monthlyMile 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…
Boat slip for boat up to 40’ rented weekly! Add to any property! $1,400 Weekly or call for lower prices
Boat slip for boat up to 40’ rented weekly! Add to any property!
$1,400 Weekly or call for lower pricesContact 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.
Coral Cove, Islamorada, Florida Keys $6,000 weekly Call for Holiday Rates
Coral Cove, Islamorada, Florida Keys
$6,000 weekly Call for Holiday RatesMM 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…
Sea Breeze Villa $12,000 Monthly, call for off season
Sea Breeze Villa
$12,000 Monthly, call for off seasonMile 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.
Southern Comfort Islamorada – Brand New $18-20,000 Monthly, call for holidays
Southern Comfort Islamorada – Brand New
$18-20,000 Monthly, call for holidaysWide 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…
Maison Residences – Unit 101 – Beachfront $14,000-$16,000 - Discounted Summer rates available
Maison Residences – Unit 101 – Beachfront
$14,000-$16,000 - Discounted Summer rates available
Maison Residences – Unit 102 – Beachfront *$8,000-$10,000 Summer Special* $12,000 - $14,000 Weekly
Maison Residences – Unit 102 – Beachfront
*$8,000-$10,000 Summer Special* $12,000 - $14,000 Weekly
Maison Residences – Unit 402 – Oceanfront & Pool Front $8,500 weekly call for holiday rates
Maison Residences – Unit 402 – Oceanfront & Pool Front
$8,500 weekly call for holiday rates
Maison Residences – Unit 203 – Oceanfront Price is in Property Description
Maison Residences – Unit 203 – Oceanfront
Price is in Property Description
Gulfview $13,000-$15,000 Monthly Call for holiday rates
Gulfview
$13,000-$15,000 Monthly Call for holiday ratesThe 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.
Sunrise Lookout $10,000 / monthly
Sunrise Lookout
$10,000 / monthlyMile 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…
Fantasy Point Villa $25,000 / monthly
Fantasy Point Villa
$25,000 / monthlyMile 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,…
Sea Ranch $9,000 weekly ~ Call for holiday rates
Sea Ranch
$9,000 weekly ~ Call for holiday ratesMile 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
Osprey Bay $7,700-$8,700 Weekly
Osprey Bay
$7,700-$8,700 WeeklyMile 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,…
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 feesMile 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
The Beach House $10,000 Weekly - Call for holiday rates
The Beach House
$10,000 Weekly - Call for holiday ratesMile 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…
Green Turtle Beach $11,500 -$14,500, Call for Holiday Rates
Green Turtle Beach
$11,500 -$14,500, Call for Holiday RatesMile 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…
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 holidays3 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…
Key Lime Villa $4,000 - $6,000 Weekly depending on dates
Key Lime Villa
$4,000 - $6,000 Weekly depending on dates3 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…
Ishmael’s Watch $20,000 / Monthly Call for Holiday rates
Ishmael’s Watch
$20,000 / Monthly Call for Holiday ratesMile 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…
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. …
Little Bay $3,000 weekly/unit
Little Bay
$3,000 weekly/unitMile 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…
Little Bay Cottage $3,000 weekly
Little Bay Cottage
$3,000 weeklyMile Marker 82 – Bayside One bedroom/two bath with Florida room. Newly remodeled. Vacation Rental License #VR-086.
Gumbo Limbo Villa $6,000 / Month
Gumbo Limbo Villa
$6,000 / MonthMM 81 – Heart of Islamorada An adorable bungalow located walking distance from the art’s district, aka ‘Down Town’ Islamorada. Walk to all the best restaurants, breweries, festivals and more! Easy parking with room for a trailered boat in the driveway. This area is ideal…
Nautica $20,000 / monthly
Nautica
$20,000 / monthlyMile 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. …
Seagrape Cottage $7,500 / Month
Seagrape Cottage
$7,500 / MonthMM 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,…
Barefoot Elegance $27,500 / monthly
Barefoot Elegance
$27,500 / monthlyMile Marker 75, 5 bedrooms, 4 baths, sleeps 10, luxurious, heated pool, deep water dockage. Boathouse with slip.
Tropical Villa $19,000 / Monthly
Tropical Villa
$19,000 / MonthlyMile 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…
Sweet Escape $20,000 - $24,000 / Monthly
Sweet Escape
$20,000 - $24,000 / MonthlySweet 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…
Palm Cottage South $15,000 / Monthly
Palm Cottage South
$15,000 / MonthlyMile 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…
Bella Del Mar $12,000 - $15,000 / Monthly
Bella Del Mar
$12,000 - $15,000 / Monthly3 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,…
Latitudes $20,000 - $25,000 / Monthly
Latitudes
$20,000 - $25,000 / MonthlyMile 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,…
Madeira Villa $20,000 / Monthly
Madeira Villa
$20,000 / MonthlyFantastic 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. …
Ocean Terrace Currently Under Construction
Ocean Terrace
Currently Under ConstructionMile 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.
Seaside Breezes $18,000-$20,000 Monthly
Seaside Breezes
$18,000-$20,000 MonthlyMile 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…
Holly’s Hideout $12,500 / Month
Holly’s Hideout
$12,500 / MonthMile 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…
Morada Breeze in Venetian Shores $6,900 - $8,000 / Month
Morada Breeze in Venetian Shores
$6,900 - $8,000 / MonthLocated 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…
Sunrise – Maison Matecumbe $5,000/ weekly - Call for holiday rates
Sunrise – Maison Matecumbe
$5,000/ weekly - Call for holiday ratesWelcome 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…
Cabana Flat – Maison Matecumbe – Oceanfront $5,500/ weekly - Call for holiday rates
Cabana Flat – Maison Matecumbe – Oceanfront
$5,500/ weekly - Call for holiday rates
Blue Heaven Bahamas $5,500 Call for Holiday Rates
Blue Heaven Bahamas
$5,500 Call for Holiday RatesTruly 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!
Seas the Day $11,000-$13,000 Monthly, Call for Holiday rates
Seas the Day
$11,000-$13,000 Monthly, Call for Holiday ratesMile 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…