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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Viewing All Rentals:
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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!
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Sunset Dream $12,000 / monthly
Sunset Dream
$12,000 / monthlyMile Marker 83. Five bedroom/four bath home located on the Florida Bay. Sunset Dream has an ideal view for Sunsets, dolphins, and a view of the Florida Bay Keys. Heated pool gives plenty of fun for the family. This home is older, but is in…
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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.
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Villa Terra Carroll $9,000 Monthly
Villa Terra Carroll
$9,000 MonthlyNew home with pool and beach access– This 4 bedroom, 4 bath house was completed in 2014 and its located near shops and entertainment in the heart of Islamorada. Relax by the heated pool while the rest of the family heads down to the beach,…
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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…
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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…
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Seaside Breezes $8,250/ monthly
Seaside Breezes
$8,250/ monthlyMile Marker 94. Three bedrooms/two baths. Ocean front in South Key Largo– this private gated home has dockage and beautiful sunrises. Sleeps 6. Monthly only.
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Ocean Terrace $4,500 weekly - $15,000 monthly
Ocean Terrace
$4,500 weekly - $15,000 monthlyMile Marker 81.5, 3 bedrooms, 3 baths with den, sleeps 6-8, Jacuzzi/splash pool and sandy beach. Vacation Rental License #VR-047.
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Aguazul $4,500 weekly - $14,000 monthly ~ Call for holiday rates
Aguazul
$4,500 weekly - $14,000 monthly ~ Call for holiday ratesMile Marker 88. Four bedroom/three baths. Sleeps 8. Ocean front estate with fantastic views, heated pool and deep water dockage. Exclusive Community. Vacation Rental License #VR-014.
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The Beach House $7,000 - $8,400 weekly ~ Call for holiday rates
The Beach House
$7,000 - $8,400 weekly ~ Call for holiday ratesIndulge 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 breathtaking panoramic ocean views from…
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Sea Ranch $8,000 weekly ~ Call for holiday rates
Sea Ranch
$8,000 weekly ~ Call for holiday ratesTwo adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. 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…
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Green Turtle Beach $10,500 / week ~ $12,500 Holidays
Green Turtle Beach
$10,500 / week ~ $12,500 HolidaysMile Marker 81. Ocean front estate located on 4 acres, five bedroom/five 1/2 baths. Sleeps 10. Sandy beach and heated pool with jacuzzi. 24 hour security. Optional separate cottage, additional $1,000 weekly. #VR-082 Please call for a more detailed 2020 rate–
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Little Bay $2,500 weekly/unit
Little Bay
$2,500 weekly/unitMile Marker 82, duplex (up and downstairs). Each unit has 2 bedrooms, 1.5 bath, sleeps 6, basin, dockage, snorkeling. Vacation Rental License #VR-084, & 85.
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Oasis At Tavernier $18,000 - $20,000 Monthly ~ Call for Holiday Rates
Oasis At Tavernier
$18,000 - $20,000 Monthly ~ Call for Holiday Rates$18,000 – $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…
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Little Bay Cottage $2,500 weekly
Little Bay Cottage
$2,500 weeklyMile Marker 82. One bedroom/two bath with Florida room. Newly remodeled. Vacation Rental License #VR-086.
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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!
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Ishmael’s Watch $18,000-$20,000 / monthly
Ishmael’s Watch
$18,000-$20,000 / monthlyMile Marker 77 — 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 or sun on…
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Grey Heron Cottage $6,500 Weekly ~ Call for holiday rates
Grey Heron Cottage
$6,500 Weekly ~ Call for holiday ratesMile Marker 89. 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 long driveway leads…
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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…
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Leila’s Beach House $4,750 / weekly
Leila’s Beach House
$4,750 / weeklyCozy, 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 the end of a quiet street…
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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…
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Osprey Bay $5,700-$6,500 Weekly, $22,000 Monthly
Osprey Bay
$5,700-$6,500 Weekly, $22,000 MonthlyMile Marker 82.7, 5 bedrooms, 3 baths, sleeps 10-12, dockage, pool, spa, and beautiful sunsets. Located in heart of Islamorada. VR-171
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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…
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Sea Shore Drive $7,200 / monthly
Sea Shore Drive
$7,200 / monthlyMile Marker 80.5. 2 BR – 2BA Large master & bath. Walk to Morada Way festivals and restaurants. Fantastic location! W/ access to neighborhood beach.
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Tatenda Ishe Cottage 2 $3,500 / monthly
Tatenda Ishe Cottage 2
$3,500 / 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.
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Tatenda Ishe Cottage 1 $3,500 / monthly
Tatenda Ishe Cottage 1
$3,500 / monthlyMile Marker 81. A neat and cozy 2 bedroom flat located in the heart of Islamorada– Walk, bike, or ride two many of Islamorada’s restaurants, breweries, and festivals–
Optional detached bedroom to add for $400/month.
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The Cove South $3,000 / monthly
The Cove South
$3,000 / monthlyMile Marker 801. 1 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 Green Turtle Inn, dinner…
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The Cove North $3,000 / monthly
The Cove North
$3,000 / monthlyMile Marker 801. 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.
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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.
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Maison Matecumbe #304 $3,300 / weekly - $9,900 monthly
Maison Matecumbe #304
$3,300 / weekly - $9,900 monthlyUnit 304 located within Maison Matecumbe gated community. Mile Marker 81. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 3 baths, 2 stories sleeps 6, pool, sandy beach. New stainless steel appliances. Vacation Rental License #VR-021
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Captains Quarters- 4 Plex $1,250 weekly - $4,750 monthly
Captains Quarters- 4 Plex
$1,250 weekly - $4,750 monthlyMile Marker 81. Two bedroom/one bath $1,450 weekly, $4,750 monthly One bedroom/one bath $1,250 weekly, $3,500 monthly Sleeps 4-6. Dockage, Wireless Internet, New A/C. #VR-127 & #VR-128
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Seagrape Cottage $7,500 / Month
Seagrape Cottage
$7,500 / MonthMM 81. 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!
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Futura Yacht club #302 $1,400 weekly, $1,600 Holidays
Futura Yacht club #302
$1,400 weekly, $1,600 HolidaysMM 88.5. 2 bedrooms, 2 baths, sleeps 4. 3rd floor. King in master W/ queen size bed in guest. Heated pool, beautiful sunsets, and lit tennis, basketball, and volleyball courts. Optional deeded dock for boats. #VR-178
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Futura Yacht Club #403 $1,400 / Week, $1,600 Holidays
Futura Yacht Club #403
$1,400 / Week, $1,600 HolidaysMM 88.5. 2 bedroom, 2 baths, sleeps 4. 4th Floor. King in master w/ 2 twins in guest. Heated pool, screened Lanai, tennis courts, basketball and volleyball courts. Optional dock for boats up to 33′. Beautiful sunsets. #VR-17
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Latitudes $16,000 / Monthly
Latitudes
$16,000 / MonthlyLarge, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal and is just minutes away from the FAMOUS Port Antigua Neighborhood beach, one of the BEST beaches in Islamorada. Port…
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Holly’s Hideout $9,000 / Month
Holly’s Hideout
$9,000 / MonthMM 91. 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 and kitchen. Two bedrooms/One…
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Morada Breeze in Venetian Shores $7,500 / Month
Morada Breeze in Venetian Shores
$7,500 / 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…
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Seas the Day $8,000 / Month *SPECIAL* $10,000 July
Seas the Day
$8,000 / Month *SPECIAL* $10,000 JulyMile marker 77. Ocean side canal. Straight shot to the Atlantic Ocean and Alligator Light House. Sunny Patio and splash Pool. 4 Bedrooms/4 Baths. Sleeps 8. Two private bedroom suits in addition to the two bedrooms with living area.
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Little Biscuit $7,500 / monthly
Little Biscuit
$7,500 / monthly -
Sunset Lagoon $5,500 / weekly $7,500 Holiday
Sunset Lagoon
$5,500 / weekly $7,500 HolidayMM 90. 5 BR. One of the best homes for families, Sunset Lagoon has 5 bedrooms nestled on the Florida Bay in Islamorada, Florida Keys. Let the kids hang out at the pool while you launch your boat out the convenient dockage to the back country or Atlantic Ocean.
This home is complete with beautiful Sunset views and a game room for the kids.
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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.
Reservation Procedure
A 30% security deposit is required along with the rental agreement and application within 24 hours to insure your booking. The security deposit is payable by credit card. A $75.00 reservation fee, cleaning fee and 12.5% sales and county tax are additional to the rental amount. The balance due is payable by check or wire transfer within 90 days prior to check in. Cancellations will be refunded in full 90 days prior to check in. The 30% security deposit will be refunded within 30 days after your departure if the property is found in satisfactory condition.
Please be advised that during the event of a hurricane, your security deposit and rental payment is fully refundable without penalty. You may also use your deposit toward a future rental at a different date.
Status of properties and prices are subject to change. If owner changes status of property, a substitution will be made or a refund will be given. Check-in is 4 PM. Check-out is 10 AM.