Vacation Rentals
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 at 305-664-3333.
Contact us at 305.664.3333 or rentals@islandvilla.com so we may help with your Florida Keys wedding plans.
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Villa Del Sol $18,000 Monthly
Villa Del Sol
$18,000 MonthlyImmaculately decorated home in Port Antigua, Villa Del Sol is a 4 bedroom, 4 bath home located water front with dockage that has easy access to both the Florida Bay and Atlantic Ocean via Channel 5. Beautifully furnished, Villa Del Sol also features multiple sunny and shady entertaining areas, a heated pool, and access to Port Antigua Beach. Port Antigua Beach is an expansive, sandy beach that only resident and guests of the neighborhood have access to.
The fourth bedroom has 2 double beds and a trundle bed which makes it perfect for kids or extended family. Experience the Keys in the perfect way. Please call for off season pricing.
Sandy Point Townie $10,000 - $11,000 Monthly
Sandy Point Townie
$10,000 - $11,000 MonthlyMile Marker 75 – Bayfront From toes in the sand to beverage in hand, this beachfront vacation rental boasts views of the beautiful blue waters of Florida Bay and is just steps away from the waters edge. After a day of sunshine, relax and enjoy…
Mango House $7,000 Monthly
Mango House
$7,000 MonthlyMile 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.
Sandy Point Duplex $2,500 - $3,500 Weekly
Sandy Point Duplex
$2,500 - $3,500 WeeklyMile Marker 75 – Bayfront This waterfront duplex is situated in an upscale community, complete with private beach. The home sits up on stilts and faces Northwest looking over the beautiful waters of Florida Bay. Watch amazing sunsets, relax under the tiki hut with your…
Blue Heaven Bahamas $5,600 / weekly
Blue Heaven Bahamas
$5,600 / weeklyTruly 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!
Virga Limbo $17,000 / monthly
Virga Limbo
$17,000 / monthlyMM 76. Five bedrooms/four baths. Charming bay front home. Hammocks, outdoor bar, and dockage all with views of uninhabited islands that dot the Keys. Sorry, no pets.
Oasis of Islamorada $6,000 Monthly
Oasis of Islamorada
$6,000 MonthlyConvenient to everything! This 2 bedroom home puts you right in the middle of the ‘Arts District’ of Islamorada. Walk to all of the best festivals, breweries, shops and celebrations! Newly remodeled, this 2 bedroom home puts you in the middle of it all. A…
Bayview Villas $4,600 - $5,600 weekly
Bayview Villas
$4,600 - $5,600 weekly3 Bedrooms & 3.5 bathrooms Villas 7-9 $3,960 – $7,000 Weekly depending on dates Mile Marker 81.6 — Bayside Villas Bayview Villas are named because they are… bayside! The closest villas to the pool, water and dockage, these villas are a set of…
Peace of Paradise $20,000 / monthly
Peace of Paradise
$20,000 / monthlyMM 75. Four bedrooms/three and a half baths. Gorgeous house over 3 floors, with heated/cooled pool in quiet, private side street in Lower Matecumbe Key. Directly on the Atlantic with open 180-degree panoramic view. Upscale interior design, fully furnished. Glass elevator. Gorgeous views from every…
Seaside Breezes $4,500/ weekly
Seaside Breezes
$4,500/ weeklyMile 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 sees it… Comfortably sleeps 6. Monthly.
Ocean Terrace $4,500 weekly - $15,000 monthly
Ocean Terrace
$4,500 weekly - $15,000 monthlyMile 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. Vacation Rental License #VR-047.
The Beach House $7,000 - $9,000 Weekly - Call for holiday rates
The Beach House
$7,000 - $9,000 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 $10,500 -$12,500, Call for Holiday Rates
Green Turtle Beach
$10,500 -$12,500, 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…
Gulfview $10,000-$12,000 Monthly
Gulfview
$10,000-$12,000 MonthlyThe 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 $2,750 weekly/unit
Little Bay
$2,750 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 $2,750 weekly
Little Bay Cottage
$2,750 weeklyMile Marker 82 – Bayside One bedroom/two bath with Florida room. Newly remodeled. Vacation Rental License #VR-086.
Angler’s Reef Garden Side $2,600 / weekly
Angler’s Reef Garden Side
$2,600 / weeklyMM 85. 2 Bedroom & 2.5 Bath. Located on the quiet side of Angler’s Reef Village. A walk down quaint streets to pool, ocean and beach!
Ishmael’s Watch $18,000-$20,000 / monthly
Ishmael’s Watch
$18,000-$20,000 / monthlyMile 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…
Grey Heron Cottage $6,500 Weekly ~ Call for holiday rates
Grey Heron Cottage
$6,500 Weekly ~ Call for holiday ratesMile Marker 89 – Oceanfront Grey Heron Cottage Estate (named after original owner) is located on the famous Millionaire’s Row. You’ll love the fantastic sun rises, ocean views, dockage and brand new pool that this property features! After entering the gated grounds, a…
Conch Villas $3,600 - $4,200 Weekly
Conch Villas
$3,600 - $4,200 Weekly3 Bedrooms & 3.5 bathrooms Villas 4-6 $3,600 – $4,200 Weekly depending on dates Mile Marker 81.6 — Bayside Villas Conch Villas, aptly named for the famous large snails that inspired the Keys to be called the ‘Conch Republic,’ are a set of three brand…
Leila’s Beach House $4,750 / weekly
Leila’s Beach House
$4,750 / weeklyMiles Marker 81 – Oceanfront Cozy, stylish house located in the heart of Islamorada. 3 Bedrooms and 2 baths located right on the ocean with a heated pool, private beach and more! Enjoy the large master bedroom with master bath and shower. Located at…
Villa Paraiso $16,000 / monthly
Villa Paraiso
$16,000 / monthlyThe extravagant Villa Paraiso boasts 6.5 bedrooms, with an 88’ dock, two Jacuzzis, veranda, and canal and bay views. Located Bayside at mm 90, the large, custom built, villa would be perfect for large families or groups. A large 10 person heated 16’x7′ swim spa…
Osprey Bay $5,700-$6,500 Weekly, $23,000 Monthly
Osprey Bay
$5,700-$6,500 Weekly, $23,000 MonthlyMile Marker 82.7 – Bayfront 5 bedrooms, 3 baths, sleeps 10-12, dockage, pool, spa, and beautiful sunsets. Located in heart of Islamorada. VR-171
Key Lime Villas $3,600 - $4,200 / weekly
Key Lime Villas
$3,600 - $4,200 / weekly3 Bedrooms & 3.5 bathrooms Villas 1-3 $3,300 – $3,850 Weekly depending on dates Mile Marker 81.6 — Bayside Villas Key Lime Villas, aptly named for the famous Key’s citrus fruit, are a set of three brand new villas located in the heart of…
Tamarind House $14,000 / monthly
Tamarind House
$14,000 / monthlyMile Marker 80.5. 3 BR – 2BA Large master & bath. Walk to Morada Way festivals and restaurants. Fantastic location! W/ access to neighborhood beach.
Tatenda Ishe Cottage $4,250 / monthly
Tatenda Ishe Cottage
$4,250 / monthlyMile Marker 81. Cute and cozy two bedroom home located off the main streets, in the heart of Islamorada. A full porch wraps around the front and back yard, for relaxing and entertaining in the Florida Keys weather. Natural sunlight fills the main living space as you enter into the quaint cottage. The fully equipped kitchen is open to the dining and the newly renovated bathroom is conveniently located in the middle of the home. Multiple cozy sitting areas lead you into the tv room, furnished with a flat screen tv and a large leather sofa. The back bedroom features french doors that extend out into a courtyard where you will find a covered sitting area and native landscaping. The guest bedroom features two twins. Enjoy being a short distance from all the charming restaurants, marinas, shops, and galleries that makes Islamorada the perfect vacation destination.
The Cove South $3,500 / monthly
The Cove South
$3,500 / monthlyMile Marker 81 – Heart of Islamorada BR – 1BA Villa on Old Hwy. This fantastic location is just a short bike ride to Morada Way festivals, the Art Walk, Full Moon Party and restaurants. Grab breakfast and Coffee at Midway Cafe, lunch at…
The Cove North $3,500 / monthly
The Cove North
$3,500 / monthlyMile Marker 81 – Heart of Islamorada 1 BR – 1BA Villa on Old Hwy. Short bike ride to Morada Way festivals and restaurants. Fantastic location! Large walk in shower. This is for the North side of the duplex.
Sunrise – Maison Matecumbe $3,500 / weekly
Sunrise – Maison Matecumbe
$3,500 / weeklySunrise is a spectacular unit within Maison Matecumbe gated community. Mile Marker 81. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 2 baths, sleeps 6, pool, sandy beach.
Moon Rise – Maison Matecumbe $3,500 / weekly
Moon Rise – Maison Matecumbe
$3,500 / weeklyMoon Rise is a spectacular unit within Maison Matecumbe gated community. Mile Marker 81. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 2 baths, sleeps 6, pool, sandy beach.
Cabana Flat – Maison Matecumbe $3,800 / weekly
Cabana Flat – Maison Matecumbe
$3,800 / weeklyUnit 301 located within Maison Matecumbe gated community. Mile Marker 81. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 2 baths, sleeps 6, pool, sandy beach. Vacation Rental License #VR-111.
Maison Residences – Brand new offering $7,500 - $10,000 Weekly
Maison Residences – Brand new offering
$7,500 - $10,000 WeeklyIntroducing Maison Residences… A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just…
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!
Latitudes $20,000 / Monthly
Latitudes
$20,000 / 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 $9,000 / Month
Holly’s Hideout
$9,000 / 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 / Month
Morada Breeze in Venetian Shores
$6,900 / 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…
Seas the Day $8,000 / Month *SPECIAL* $10,000 July
Seas the Day
$8,000 / Month *SPECIAL* $10,000 JulyMile 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. Two private bedroom suits on second floor in addition to the two…
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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