Islamorada Rentals, Key Largo Rentals & FL Keys Vacation Rentals
Your Islamorada rental, Tavernier rental and Key Largo rental search starts (and ends!) here. At Island Villa, we’re pleased to list the most luxurious and stunning Florida Keys vacation rentals. When searching for the perfect Florida Keys rental home for you or your family, we want you to have the most information at your fingertips, so our Keys property listings include virtual tours and photos. Island Villa is your native connection to paradise, and we are here to help you explore your options for a dream Florida Keys vacation.
A FL Keys vacation is sure to make cherished tropical memories. Escape to your Islamorada vacation rental retreat or Key Largo vacation hideaway and enjoy the island life. Whether your FL Keys vacation is action-packed with fishing, diving and exploring the sparkling waters of the Keys, or it’s spent swaying in a hammock suspended between two palms, you can enjoy it all from our Florida Keys rentals. Enjoy world-class snorkeling or kayak the shallow flats from the backyard of our waterfront vacation homes. Our goal is to accommodate you from the beginning of FL Keys vacation planning through your stay at one of our Key Largo, Tavernier or Islamorada rentals – or anywhere in between. Whether you’re renting a home in Islamorada or Key Largo for a vacation, wedding, corporate event, or family reunion, our accommodations are sure to please. Our rentals offer breathtaking views and designer interiors that capture the charm and beauty of the FL Keys.
Our Florida Keys Vacation rentals are listed by mile marker and categorized by location – Atlantic Ocean or Florida Bay – type of rental – townhomes, condos or flats – and by access to waterways, canals or lagoons.
For more information on any of the Florida Keys rental properties below, check the box next to the property in which you are interested, and complete the form at the bottom of the page to receive additional information. To explore the individual charms of our luxury vacation rental properties call us.
STAY FOR A WEEK… OR FOREVER…!
Contact us at 305.664.3333 or rentals@islandvilla.com so we may help with your Florida Keys rental plans.
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New Property – Sun Kissed Retreat $25,000 Monthly
New Property – Sun Kissed Retreat
$25,000 MonthlyMile Marker 75 – Open Bayfront Old Florida Charm Meets Island Comfort | Lower Matecumbe Key Vacation Retreat Welcome to your private slice of paradise in Islamorada, nestled bayside on the quiet and serene part of Lower Matecumbe Key. This beautifully maintained rental home captures…
Reel Paradise $15,000 Monthly / Call for off season
Reel Paradise
$15,000 Monthly / Call for off seasonMile Marker 74 – Bayside, Canal front Canal-Front Retreat with Pool & Prime Dockage | Lower Matecumbe Key, Islamorada Welcome to your perfect slice of paradise on Lower Matecumbe Key—where tropical tranquility meets world-class water access. This canal-front gem offers the ultimate Florida Keys escape,…
Green Coconut, Islamorada $12,500 Monthly, call for high season
Green Coconut, Islamorada
$12,500 Monthly, call for high season
Maison Residences – 8 Bedrooms – Full Floor steps to beach $18,000-$24,000 Weekly
Maison Residences – 8 Bedrooms – Full Floor steps to beach
$18,000-$24,000 WeeklyPlease call for holiday rates 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…
Summer Seas $3,500 Monthly
Summer Seas
$3,500 MonthlyWelcome to your dream escape at Summer Seas, where island living is as effortless as the ocean breeze. This beautifully furnished one-bedroom, one-bath condo is a sanctuary of style and comfort, designed with impeccable attention to detail. From brand-new appliances to elegant furnishings that enhance…
Leisure Inn Islamorada $9,000-$10,000 Monthly, Call for Holiday rates
Leisure Inn Islamorada
$9,000-$10,000 Monthly, Call for Holiday ratesStunning 3 Bedroom, 2 Bath Canal Front Home in Islamorada – Monthly Rentals Only Escape to paradise with this beautiful canal front home off the beaten path on Lower Matecumbe Key in sunny Islamorada…. Offering the perfect blend of luxury, comfort, and adventure! Nestled…
Galleon Cove *NEW* $12,000-$14,000 Monthly, call for off season
Galleon Cove *NEW*
$12,000-$14,000 Monthly, call for off season
Creekside Cabana In Venetian Shores $20,000 Monthly, call for Holiday
Creekside Cabana In Venetian Shores
$20,000 Monthly, call for Holiday
Blue Oasis Estate $12,500 Weekly - Call for holiday rates
Blue Oasis Estate
$12,500 Weekly - Call for holiday ratesMile 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…
Key Largo Ocean Resort 276 $7,500 Monthly * Discount
Key Largo Ocean Resort 276
$7,500 Monthly * DiscountEscape 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…
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.
Sunrise Lookout $10,000 / monthly
Sunrise Lookout
$10,000 / monthlyMile Marker 82 – Oceanfront Oasis | “Sunrise Lookout” Upstairs Unit | Monthly Rental Perched above the turquoise shimmer of the Atlantic Ocean, Sunrise Lookout is your private retreat in the heart of Islamorada, located at the iconic Mile Marker 82. This elevated haven, available…
*NEW* Venetian Moon $22,000 / monthly
*NEW* Venetian Moon
$22,000 / monthlyMile Marker 86 – Open Bayfront Welcome to your dream retreat in Islamorada, nestled in the exclusive Venetian Shores neighborhood. This meticulously appointed, custom-built 5-bedroom, 5.5-bath home offers an extraordinary escape for those seeking elegance and relaxation in the Florida Keys. Step into…
Happy Ours $30,000 / monthly
Happy Ours
$30,000 / monthlyMile Marker 74.5 – Open Bayfront Welcome to Happy Ours – an exquisite six-bedroom, six-bathroom waterfront estate offering over 5,000 square feet of air-conditioned luxury and an additional 4,500 square feet of expansive covered terraces and deck space. Nestled in the prestigious Port Antigua gated…
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
Maison Residences – Unit 402 – Oceanfront & Pool Front $6,500 Weekly, call for holiday rates
Maison Residences – Unit 402 – Oceanfront & Pool Front
$6,500 Weekly, 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...
Blue Heaven Bahamas $7,000-$8,000, Call for Holiday Rates
Blue Heaven Bahamas
$7,000-$8,000, 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!
Nautica $25,000 / monthly
Nautica
$25,000 / 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. …
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…
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.
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…
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
Green Turtle Beach $13,500 -$15,000, Call for Holiday Rates
Green Turtle Beach
$13,500 -$15,000, 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…
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.
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…
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 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.
Key Largo Ocean Resort 248 $15,000 Monthly
Key Largo Ocean Resort 248
$15,000 MonthlyEscape 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…
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…
Osprey Bay $8,000-9,000 Weekly
Osprey Bay
$8,000-9,000 WeeklyMile Marker 82.7 – Bayfront Experience the Ultimate Bayfront Getaway in Islamorada! Welcome to your dream vacation rental in the heart of Islamorada, nestled along the serene bayfront in the picturesque Florida Keys. This charming 5-bedroom, 3-bathroom home offers a perfect blend of tranquility, comfort,…
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…
Sunrise – Maison Matecumbe $3,500- 5,000/ weekly - Call for holiday rates
Sunrise – Maison Matecumbe
$3,500- 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…
Maison Residences – Unit 101 – Beachfront $15,000 Weekly, Summer Only Discount $8k-$10k
Maison Residences – Unit 101 – Beachfront
$15,000 Weekly, Summer Only Discount $8k-$10k
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...
Maison Residences – Unit 204 – Oceanfront $8-10,000 WEEKLY $12,500 WEEKLY RENTAL SEASON
Maison Residences – Unit 204 – Oceanfront
$8-10,000 WEEKLY $12,500 WEEKLY RENTAL SEASON$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…
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 $8-10,000 WEEKLY FALL SEASON $13,500 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...
Maison Residences – Unit 202 – Oceanfront $8-10,000 WEEKLY $12,500 WEEKLY RENTAL SEASON
Maison Residences – Unit 202 – Oceanfront
$8-10,000 WEEKLY $12,500 WEEKLY RENTAL SEASON
$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...
Maison Residences – Unit 201 – Oceanfront $8-10,000 WEEKLY $12,500 WEEKLY RENTAL SEASON
Maison Residences – Unit 201 – Oceanfront
$8-10,000 WEEKLY $12,500 WEEKLY RENTAL SEASON$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…
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,…
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. …
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…
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…
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,…
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 / MonthVenetian Shores Hideaway | 2 Bed • 1 Bath • Monthly Rental Canalfront Living with Private Pool & Dockage Nestled in the exclusive enclave of Venetian Shores, this charming 2-bedroom, 1-bath lower-level retreat offers the perfect balance of island comfort and outdoor adventure. With direct…
Seas the Day $8,000 Monthly, Call for In Season rates
Seas the Day
$8,000 Monthly, Call for In Season ratesWelcome to your perfect getaway in Islamorada. This 4-bedroom, 4-bath home sits along a deep-water canal on the ocean side, offering direct access to the sparkling blue-green waters of the Atlantic Ocean and Alligator Reef Light. Whether you’re heading out for a day of fishing…
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.
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