Vacation Rentals

Paradise awaits for your idyllic FL Keys vacation,

… from your “native connection”

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.

Ocean Rentals

Bay Rentals

Canal Rentals

Condo & Flat Rentals

Viewing All Rentals:

MM 85. 2 Bedroom & 2.5 Bath. Two spacious bedrooms and two and a half bath, sleeps six. Enjoy the Beautiful garden views and ocean breezes from these island-style villas or relax poolside. Nestled amidst quaint streets and walking paths, their design takes inspiration from…

2 beds 2.5 baths
2 beds 2.5 baths

Sandy Point Duplex $2,500 - $3,500 Weekly

Sandy Point Duplex

$2,500 - $3,500 Weekly

Mile 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…

3 beds 3 baths
3 beds 3 baths

Coral Cove, Islamorada, Florida Keys $3,500 - $4,000 / weekly

Coral Cove, Islamorada, Florida Keys

$3,500 - $4,000 / weekly

MM 81.5.  BRAND NEW construction located in the Heart of Islamorada!  Coral Cove is a secluded and intimate gated community of 9 homes on the Florida Bay.   Featuring both a private pool in the back, and a community pool on the bay, Coral Cove…

3 beds 3.5 baths
3 beds 3.5 baths

Sandy Point Townie $10,000 - $11,000 Monthly

Sandy Point Townie

$10,000 - $11,000 Monthly

Mile 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…

3 beds 2.5 baths
3 beds 2.5 baths

Villa Del Sol $17,000 Monthly

Villa Del Sol

$17,000 Monthly

Immaculately 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.

4 beds 4 baths
4 beds 4 baths

Gulfview $10,000-$12,000 Monthly

Gulfview

$10,000-$12,000 Monthly

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
3 beds 2 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.

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Oceanfront Beach Cottages

4 beds 3 baths
4 beds 3 baths

Green Turtle Beach $10,500 -$12,500, Call for Holiday Rates

Green Turtle Beach

$10,500 -$12,500, 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
5 beds 5.5 baths

The Beach House $7,000 - $9,000 Weekly - Call for holiday rates

The Beach House

$7,000 - $9,000 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
4 beds 4 baths

Introducing 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…

4 beds 4.5 baths
4 beds 4.5 baths

Moon Rise is a spectacular unit within Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81.   Newly done pool  and Hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy…

3 beds 3 baths
3 beds 3 baths

Sunrise is a spectacular unit within the Maison Matecumbe gated community.  Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 3 baths, sleeps 6, pool, sandy…

3 beds 3 baths
3 beds 3 baths

Mango House $7,000 Monthly

Mango House

$7,000 Monthly

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.

2 beds 2.5 baths
2 beds 2.5 baths

Osprey Bay $6,500-$7,500 Weekly, $23,000 Monthly

Osprey Bay

$6,500-$7,500 Weekly, $23,000 Monthly

Mile Marker 82.7 – Bayfront 5 bedrooms, 3 baths, sleeps 10-12, dockage, pool, spa, and beautiful sunsets. Located in heart of Islamorada. VR-171  

5 beds 3 baths
5 beds 3 baths

Ishmael’s Watch $18,000-$20,000 / monthly

Ishmael’s Watch

$18,000-$20,000 / monthly

Mile 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…

7 beds 4 baths
7 beds 4 baths

Leila’s Beach House $4,750 / weekly

Leila’s Beach House

$4,750 / weekly

Miles 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…

3 beds 2 baths
3 beds 2 baths

Seas the Day $8,000 / Month *SPECIAL* $10,000 July

Seas the Day

$8,000 / Month *SPECIAL* $10,000 July

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. Two private bedroom suits on second floor in addition to the two…

4 beds 4 baths
4 beds 4 baths

Latitudes $20,000 / Monthly

Latitudes

$20,000 / 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
4 beds 2.5 baths

Oasis of Islamorada $6,000 Monthly

Oasis of Islamorada

$6,000 Monthly

Convenient 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…

2 beds 2 baths
2 beds 2 baths

Nautica $20,000 / monthly

Nautica

$20,000 / monthly

Mile Marker 83 – Bayfront Four bedroom/four bath clean home located directly on the Florida Bay.  Featuring fantastic sunset views, dockage and a heated pool, Nautica Sleeps 8-10 and has a heated pool and good dockage.   Monthly rental only.

4 beds 4 baths
4 beds 4 baths

Holly’s Hideout $9,000 / Month

Holly’s Hideout

$9,000 / 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
4 beds 3 baths

Bayview Villas $4,600 - $5,600 weekly

Bayview Villas

$4,600 - $5,600 weekly

3 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…

3 beds 3.5 baths
3 beds 3.5 baths

Key Lime Villas $3,600 - $4,200 / weekly

Key Lime Villas

$3,600 - $4,200 / weekly

3 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…

3 beds 3.5 baths
3 beds 3.5 baths

Conch Villas $3,600 - $4,200 Weekly

Conch Villas

$3,600 - $4,200 Weekly

3 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…

3 beds 3.5 baths
3 beds 3.5 baths

Little Bay $2,750 weekly/unit

Little Bay

$2,750 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
2 beds 2 baths

Little Bay Cottage $2,750 weekly

Little Bay Cottage

$2,750 weekly

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

1 bed 2 baths
1 bed 2 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!  

2 beds 2 baths
2 beds 2 baths

Tatenda Ishe Cottage $4,250 / monthly

Tatenda Ishe Cottage

$4,250 / monthly

Mile 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.

2 beds 2 baths
2 beds 2 baths

Villa Paraiso $16,000 / monthly

Villa Paraiso

$16,000 / monthly

The 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…

7 beds 4.5 baths
7 beds 4.5 baths

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
2 beds 1 bath

Virga Limbo $17,000 / monthly

Virga Limbo

$17,000 / monthly

MM 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.  

5 beds 4 baths
5 beds 4 baths

Seaside Breezes $4,500/ weekly

Seaside Breezes

$4,500/ weekly

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 sees it…  Comfortably sleeps 6.        Monthly.  

3 beds 2 baths
3 beds 2 baths

Ocean Terrace $4,500 weekly - $15,000 monthly

Ocean Terrace

$4,500 weekly - $15,000 monthly

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. Vacation Rental License #VR-047.  

3 beds 3 baths
3 beds 3 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
5 beds 4 baths

Blue Heaven Bahamas $5,600 / weekly

Blue Heaven Bahamas

$5,600 / weekly

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
3 beds 3 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
6 beds 7 baths

Unit 301 located within Maison Matecumbe gated community. Maison Matecumbe is a small 9 unit condo located just off the old road in Islamorada at mile marker 81. Newly done pool and hot tub! 3 bedrooms, 2 baths, sleeps 6, pool, sandy beach. Vacation Rental…

3 beds 2 baths
3 beds 2 baths

Grey Heron Cottage $6,500 Weekly ~ Call for holiday rates

Grey Heron Cottage

$6,500 Weekly ~ Call for holiday rates

Mile 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…

3 beds 2.5 baths
3 beds 2.5 baths

Peace of Paradise $20,000 / monthly

Peace of Paradise

$20,000 / monthly

MM 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…

4 beds 3.5 baths
4 beds 3.5 baths

Tamarind House $14,000 / monthly

Tamarind House

$14,000 / monthly

Mile Marker 80.5. 3 BR – 2BA Large master & bath. Walk to Morada Way festivals and restaurants. Fantastic location! W/ access to neighborhood beach.  

3 beds 2 baths
3 beds 2 baths

The Cove North $3,500 / monthly

The Cove North

$3,500 / monthly

Mile 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.

1 bed 1 bath
1 bed 1 bath

The Cove South $3,500 / monthly

The Cove South

$3,500 / monthly

Mile 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…

1 bed 1 bath
1 bed 1 bath

Treehouse $5,000 / monthly

Treehouse

$5,000 / monthly

Mile Marker 96, 1 bedroom, 1 bath, sleeps 4, dock, beach, and sunsets.  

1 bed 1 bath
1 bed 1 bath
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