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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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…
Venetian Villa – Brand New $25,000 / monthly
Venetian Villa – Brand New
$25,000 / monthlyMile 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…
Paradise Found- w/ incredible neighborhood beach! $15,000 / Monthly *$11,000 Summer & Fall Special*
Paradise Found- w/ incredible neighborhood beach!
$15,000 / Monthly *$11,000 Summer & Fall 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…
Creekside Cabana In Venetian Shores $25,000-$27,000 Monthly
Creekside Cabana In Venetian Shores
$25,000-$27,000 Monthly
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…
New Property: Leisure Inn Islamorada $9,000-$10,000 Monthly, Call for Holiday rates
New Property: 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…
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…
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 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…
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…
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…
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…
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,…
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.
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…
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…
Maison Residences – Unit 102 – Beachfront $12,000 - $14,000 Weekly
Maison Residences – Unit 102 – Beachfront
$12,000 - $14,000 Weekly
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...
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...
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...
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,…
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…
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…
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…
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.
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...
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.
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
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...
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…
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…
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…
Osprey Bay $8,000-9,000 Weekly
Osprey Bay
$8,000-9,000 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,…
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…
Nautica $22,000 / monthly
Nautica
$22,000 / 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. …
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…
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…
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…
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.
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,…
Morada Breeze in Venetian Shores $6,900 - $8,000 / Month
Morada Breeze in Venetian Shores
$6,900 - $8,000 / MonthLocated in the prestigious Venetian Shores, this 2-bedroom lower-level unit offers a perfect blend of comfort and access to the outdoors. Enjoy a private pool and dockage with direct access to the ocean via Snake Creek, where the iconic blue-green waters and legendary Islamorada fishing…
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.
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.
Blue Heaven Bahamas $7,000 Call for Holiday Rates
Blue Heaven Bahamas
$7,000 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!
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. …
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