Florida Keys Vacation Rentals

Islamorada Rentals, Key Largo Rentals & FL Keys Vacation Rentals




Paradise awaits for your idyllic FL Keys vacation, from your native connection

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.

Explore All Florida Keys Rentals Now


  • Island Villa Vacation Rentals - Sea Ranch
  • Island Villa Vacation Rentals - The Beach House
  • Island Villa Vacation Rentals - Green Turtle

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Florida Keys Rentals on the Ocean Florida Keys Vacation Rentals on Florida Bay Florida Keys Condos, Townhomes & Flats Lagoons, Canals & Waterways in the Florida Keys Vacation in Abaco, Bahamas Only the Top Shelf Estates Pet Friendly Estates and Cottages

 






Island Villa Rental's Newest & Freshest Offerings

Maison Townhouse #306
$3,000 Weekly
MM 81. Unit 306 located within Maison Matecumbe gated community. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach. Vacation Rental License #VR-124.
GREY HERON COTTAGE
$6,500 Weekly
MM 89. 3 bedroom/ 3 bath. Vintage Florida home newly remodeled with brand new pool and dockage on large private estate off Millionaire's Row. Brand new pool is finished! Stay tuned for awesome new photos!
TAHITIAN FALLS
$12,000-14,000 monthly
MM 76. Three bedrooms/four baths. Bayfront home with heated lagoon style pool, landscapes, Large Tiki hut with TV and bar, dockage, game room and more! Enjoy the Keys like intended, outdoors in the sun and breeze at the paradise playground. Sleeps 6.
OCEAN COTTAGE
$6,000 Weekly
MM 80. Vintage Florida home located directly on Ocean! Screened in porch looks over the Ocean, pool and tropical landscaping. Perfect location off Old Highway in Upper Matecumbe. 3BR main house with separate 1BR cottage. All with over 90' of serene sandy beach.
ISHMAEL'S WATCH
$18,000 monthly, $20,000 Holiday SeasonPart of our "Pet-Friendly Collection"
MM 77. Seven bedroom/ five 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 and Jacuzzi. Catch palm tree shade or sun on the private beach, steps away from the pool! Estate comes with private dockage located just around the corner on the canal.
OASIS AT TAVERNIER
$18,000 to $20,000 Monthly
~Call for holiday rates
Part of our "Top Shelf Rental Collection"
Mile Marker 92. Six bedrooms/seven bath gated estate on the water with easy access to the Atlantic Ocean. Sleeps 12. Luxurious residence with lavish furnishings and amenities. This top-tier house has everything you could dream of... Gourmet kitchen and dining, state-of-the-art theatre room, an ocean viewing deck and more! Pool and great dockage with direct ocean access. Inquire for a complete list of amenities and features. Please Call for Holiday rates.

Florida Keys Rentals On The Ocean

GREY HERON COTTAGE
$6,500 Weekly
MM 89. 3 bedroom/ 3 bath. Vintage Florida home newly remodeled with brand new pool and dockage on large private estate off Millionaire's Row. Brand new pool is finished! Stay tuned for awesome new photos!
PEACE OF PARADISE
$20,000 monthly

NEW LISTING, some restrictions

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 room. Includes amenities like kayaks and bikes. Enough dockage space for 2 boats, boat lift available for extra charge. Boat rental also possible. Best Sunrises and Sunsets in the Florida Keys! Very quiet and upscale neighborhood, safe and secluded.
OASIS AT TAVERNIER
$18,000 to $20,000 Monthly
~Call for holiday rates
Part of our "Top Shelf Rental Collection"
Mile Marker 92. Six bedrooms/seven bath gated estate on the water with easy access to the Atlantic Ocean. Sleeps 12. Luxurious residence with lavish furnishings and amenities. This top-tier house has everything you could dream of... Gourmet kitchen and dining, state-of-the-art theatre room, an ocean viewing deck and more! Pool and great dockage with direct ocean access. Inquire for a complete list of amenities and features. Please call for holiday rates.
ISHMAEL'S WATCH
$18,000 monthly, $20,000 Holiday SeasonPart of our "Pet-Friendly Collection"
MM 77. Six bedroom/ five 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 and Jacuzzi. Catch palm tree shade or sun on the private beach, steps away from the pool! Estate comes with private dockage located just around the corner on the canal.
VILLA THENARDIER
$12,500 Weekly, $35,000 monthly, call for holidays
Part of our "Top Shelf Rental Collection"
MM 89. Four Bedroom/ six bath, ultra-luxurious, oceanfront estate with more than 6,000 square feet under air and 5500 square feet of covered terraces and deck. Featuring a gourmand's kitchen, home theatre, gym, pool table, tennis court , pool, Jacuzzi, outdoor kitchen and more! Located on three secluded tropical acres on the Atlantic Ocean.
GREEN TURTLE BEACH
$9,950 weekly, $13,140 Holidays
Part of our "Top Shelf Rental Collection"
Mile 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
SEA RANCH
$8,000 weekly - $24,000 monthly
Mile Marker 83. Cottage 1: oceanfront, one bedroom/ one bath upstairs. One bedroom/one bath downstairs with separate entrance. Sleeps 4.
Cottage 2: Two bedroom/one bath. Sleeps 4-6. Private beach, observing pier, wet bar, pool table & newly remodeled. #VR-123
Destination Wedding Location
   
OCEAN COTTAGE
$6,000 Weekly
MM 80. Vintage Florida home located directly on Ocean! Screened in porch looks over the Ocean, pool and tropical landscaping. Perfect location off Old Highway in Upper Matecumbe. 3BR main house with separate 1BR cottage. All with over 90' of serene sandy beach.
AGUAZUL
$4,500 weekly - $14,000 monthly
~Call for holiday rates
Mile 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.
OCEAN TERRACE
$4,500 weekly - $15,000 monthly
Mile Marker 81.5, 3 bedrooms, 3 baths with den, sleeps 6-8, Jacuzzi/splash pool and sandy beach. Vacation Rental License #VR-047.
SEASIDE BREEZES
$8,250 monthly
Mile Marker 94. Three bedrooms/two baths. Sleeps 6. Ocean front, dockage, sunrises.
THE BEACH HOUSE
$6,500 weekly
$8,000 Holidays, spring break & Mini Season monthly
MM 81. Situated right on the Atlantic Ocean right on the old road in The Heart of Islamorada! A view of the water from most rooms, the Main house has 3 bed/3baths. Guest cottage has 1bd/1ba. Nestled amongst lush tropical gardens and gated for total privacy. Take a morning run or bike ride and walk to all the restaurants, galleries and shops located along Morada Way Arts & Cultural District! Enjoy the expansive waterside pool and patio and breezy gazebo whilst planning the next relaxed event for your holiday - al fresco dining, party at the tiki bar, or jumping in your skiff at the end of the dock! Note: Skiff dockage, shallow access. #VR-209
EZ ANCHOR INN
$12,500 monthly
Mile Marker 74.5. Private ocean front with spacious sand beach! 3 bedroom/2 bath upstairs and two 1bedroom/1bath apartments downstairs makes this a great space for extended family or group vacations. Light and bright, the house features an open concept living & dining areas and a wide patio balcony. Two adorable downstairs apartments are roomy and bright, and walk out to the private beach. Incredible ocean views abound!
ANGLER'S REEF VILLAGE
Oceanside, Windley Key,
Islamorada

$2,900 weekly - $10,200 monthly
~Call for holiday Rates
MM 85. Two spacious bedrooms and two and a half bath, sleeps six. Enjoy the Beautiful ocean and garden views from these island-style villas or relax poolside out your French doors. Nestled amidst quaint streets and walking paths, their design takes inspiration from Native Conch and Key West themes. Relax pool side with Ocean front view. This unit does not come with a boat slip. #VR-148
 
SEA BISCUIT
$10,000 monthly
MM 74. Three bedrooms/two baths. Oceanfront home with private beach.

Florida Keys Vacation Rentals On Florida Bay

TAHITIAN FALLS
$12,000-14,000 monthly
MM 76. Three bedrooms/four baths. Bayfront home with heated lagoon style pool, landscapes, Large Tiki hut with TV and bar, dockage, gameroom and more! Enjoy the Keys like intended, outdoors in the sun and breeze at the paradise playground. Sleeps 6.
SLICE OF HEAVEN
$4,250 weekly, $12,750 monthly
~Call for holiday rates
MM 75. Three bedrooms/two baths. Newly remodeled bay front home on a large, beautiful piece of land. Beautiful sunsets and dockage included. Weekly coming soon.
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.
NAUTICA
$20,000 monthly
Mile Marker 83. Four bedroom/four bath. Sleeps 8-10. Bayfront, pool, dockage.
SUNSET DREAM
$12,000 monthlyPart of our "Pet-Friendly Collection"
Mile Marker 83. Five bedroom/four bath. Bayfront, pool and dockage.
LITTLE BAY
$2,500 weekly - $7,500 monthly/unit
Mile 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.
Destination Wedding Location
LITTLE BAY COTTAGE
$2,500 weekly - $7,500 monthly
Mile Marker 82. One bedroom/two bath with florida room. Newly remodeled. Vacation Rental License #VR-086.
TREEHOUSE
$5,000 monthly rental only
Mile Marker 96, 1 bedroom, 1 bath, sleeps 4, dock, beach, and sunsets.
OSPREY BAY
$5,700-$6,000 weekly, $18,500 monthly
Mile Marker 82.7, 5 bedrooms, 3 baths, sleeps 10-12, dockage, pool, spa, and beautiful sunsets. Located in heart of Islamorada. VR-171
LA JOLLA
$3,500 weekly

$10,500 monthly
Three bedroom/three bath. Sleeps 6. Located in central Islamorada. Shared pool. Within walking distance to shopping and restaurants. Bayfront, dockage and sunsets. #VR-129

Florida Keys Condos, Townhomes & Flats

SUNSET BEACH
$5,400 monthly
MM 74. Two bedroom townhome with dockage and access to a 300' members only white sand beach on Bayside. Dockage for boats up to 24' with great access to both Ocean and Bay.
BLUE FIN
$4,000 monthly
MM 81. One bedroom/one bath. Newly remodeled, cozy cottage conveniently located in Upper Matecumbe, Islamorada.
SEASHORE DRIVE
$7,200 monthly
Mile Marker 80.5. 2 BR - 2BA Large master & bath. Walk to Morada Way festivals and restaurants. Fantastic location! W/ access to neighborhood beach.
SAND PEBBLES
$3,000-$3,500 monthly
MM 80. Two bedroom/two bath. Pool, tiki hut, balcony and gardens! Conveniently located
MARINERS CLUB
$2,800 weekly
MM 97. Three bedrooms - three baths steps away from the pool and open water view! Living area opens up to a great covered balcony. There is a separate dock available to add on through dockmaster. Located in the luxurious Mariners Club Condo, unit 402.
FUTURA YACHT CLUB #302
$1,400 weekly, $1,600 Holidays
MM 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
FUTURA YACHT CLUB #403
$1,400 weekly, $1,600 Holidays
MM 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-177
CABANA FLAT - MAISON MATECUMBE
$3,000 weekly - $9,000 monthly
Unit 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 MATECUMBE #304
$3,300 weekly - $9,900 monthly
Unit 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
Maison Townhouse #306
$3,000 Weekly
MM 81. Unit 306 located within Maison Matecumbe gated community. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 3 baths, sleeps 6, pool, sandy beach. Vacation Rental License #VR-124.
SUNRISE TOWNIE - MAISON MATECUMBE
$3,500 weekly
Unit 309 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, oceanside unit with beautiful sunrise views! #VR-027
CAPTAINS QUARTERS - 4 PLEX
$1,250 weekly - $4,750 monthly
Mile 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
SEAGRAPE
$7,500 monthly
MM 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!

Lagoons, Canals & Waterways In The Florida Keys

BAREFOOT ELEGANCE
$27,500 monthly
Mile Marker 75, 5 bedrooms, 4 baths, sleeps 10, luxurious, heated pool, deep water dockage. Boathouse with slip.
HOLLY'S HIDEOUT
$8,500 monthly
MM 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 bath downstairs with breakfast bar for guests convenience. Spacious screened porch overlooking the awesome alfresco deck and furnished with plenty of outdoor deck for lounging and relaxing away your vacation!
OCEANISTA
$10,000 monthly
Mile Marker 75. Very Private - Two Bedrooms / Two Baths. Sleeps 6. Private waterfront lagoon to accommodate deep water boaters. Oceanfront 'Walking Beach' just steps away!
SEAS THE DAY
$8,000 monthly *SPECIAL*
Usually $10,000 Monthly
Mile 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.
   
LITTLE BISCUIT
$7,500 monthly
MM 74. Three bedrooms/1 bath. Canal front home with beach access.

Property in Hope Town, Elbow Cay, Abaco, Bahamas

BLUE HEAVEN, BAHAMAS
$4,860 weekly
3br/3ba airy cottage with spectacular view of Hope Town lighthouse. Pool and pink sand beach!

Please contact us at rentals@islandvilla.com or contact Robin at 305.664.3333

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