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 – La Playa
  • 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

 

Florida Keys Rentals On The Ocean
LA PLAYA
$9,500 weekly - $28,500 monthly 		Mile Marker 76.5. Main House: 4 bedrooms, 3 baths, sleeps 6-8. Cottage: 3 bedrooms, 2 baths, sleeps 6-8. Jacuzzi, sandy beach, pool, dockage, fishing pier, 5 acres & 350 ft of sandy beach.
Destination Wedding Location 		Main House - View Photos »
Cottage - View Photos » Virtual Tour »
CASA AQUA
$10,000 weekly - $30,000 monthly 		Mile Marker 20 - Cudjoe Key. Main House is five bedrooms/three 1/2 luxury baths. Guest cottage is one bedroom/one bath. Heated infinity pool, sunrise, nature trail, dockage, sauna, Jacuzzi and luxuriously furnished. View Photos »
GREEN TURTLE BEACH
$8,500 weekly - $29,500 monthly, $10,200 Holidays
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.
 View Photos » Virtual Tour »
GREEN TURTLE BEACH II
$8,500 weekly - $29,500 monthly, $10,200 Holidays 		Mile Marker 81. Ocean front estate located on 4 acres, four bedrooms/four baths. Sleeps 8. Sandy beach and heated pool with jacuzzi. 24 hour security. View Photos »
SEA RANCH
$7,000 weekly - $21,000 monthly		 Mile Marker 83. Cottage 1: oceanfront, one bedroom/ one bath upstairs. One bedroom/one bath downstairs with separate entrance. Sleeps 4-6.
Cottage 2: Two bedroom/one bath. Sleeps 4-8. Private beach, observing pier, wet bar, pool table & newly remodeled. #VR-09-132
Destination Wedding Location 		View Photos »
AGUAZUL
$5,500 weekly - $16,500 monthly 		Mile Marker 88. Four bedroom/three baths. Sleeps 8. Ocean front estate, heated pool and deep water dockage. Exclusive Community. Vacation Rental License #VR-09-82. View Photos »
OCEAN TERRACE
$4,200 weekly - $12,600 monthly 		Mile Marker 81.5, 3 bedrooms, 3 baths with den, sleeps 6-8, Jacuzzi/splash pool and sandy beach. Vacation Rental License #VR-09-89. View Photos » Virtual Tour »
SAIL AWAY
$3,400 weekly - $10,000 monthly, $4,000 weekly Holidays 		Mile Marker 77, 3 bedrooms, 2 baths, sleeps 8-10, white sandy beach, beautiful sunrises.
#VR-09-133 		View Photos »
Virtual Tour »
SEA BISCUIT
$10,000 monthly 		Mile Marker 74, 3 bedrooms, 3 baths, sleeps 6-8, beautiful sandy beach, sunrises, with 30' deep water dockage. View Photos »
Virtual Tour »
SEASIDE BREEZES
$8,250 monthly 		Mile Marker 94. Three bedrooms/two baths. Sleeps 6. Ocean front, dockage, sunrises. View Photos »
TWISTED PALMS
$13,500 monthly		 Mile Marker 75. Main House is three bedroom/three baths. Sleeps 8.
Guest House is one bedroom/one bath. Sleeps 4. Pool, Private Beach, Sunrise. 		View Photos »
Virtual Tour »
THE PIER
$5,000 weekly, $12,000 monthly		 MM 82.5. “Over the top” privacy at The Pier, Islamorada’s newest ocean side residence and most secluded address. Ocean front home features 4 bedrooms and 3.5 baths. Sleeps 8. Tropical hardwood floors and tasteful décor make this a comfortable island escape. Large balcony is ideal for al fresco dining and enjoying awesome sunrises. Features a tiki hut on the private sandy beach and a long pier, perfect for relaxing under the sun or stars. Amenities: Tennis courts, pool and gated privacy. View Photos »

Florida Keys Vacation Rentals On Florida Bay
NAUTICA
$18,000 monthly		 Mile Marker 83. Four bedroom/four bath. Sleeps 8-10. Bayfront, pool, dockage. View Photos »
SUNSET DREAM
$9,900 monthly		 Mile Marker 83. Five bedroom/three bath. Bayfront, pool and dockage. View Photos »
BAY BREEZES
$10,000 monthly 		Mile Marker 74. Two bedroom/two baths upstairs. One bedroom/one bath downstairs. Bayfront, Deep Dockage & Sunsets! View Photos »
JETSON HOUSE
$3,000 monthly 		Mile Marker 74. One bedroom/one bath. Sandy beach & sunsets! View Photos »
INDIAN WATERWAYS
$4,500 monthly 		Mile Marker 88. Two bedroom/one bath. Sleeps 4. Bayfront with sunsets, deep dockage and boat ramp. View Photos »
LITTLE BAY
$2,400 weekly -
$7,200 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-09-87,88.
Destination Wedding Location		 View Photos »
Virtual Tour »
LITTLE BAY COTTAGE
$2,400 weekly - $7,200 monthly 		Mile Marker 82. One bedroom/two bath with florida room. Newly remodeled. Vacation Rental License #VR-09-86. View Photos »
Virtual Tour »
HIDEAWAY
$1,800 weekly - $5,500 monthly 		Mile Marker 74.5, 3 bedrooms, 2 baths, sleeps 6, dock, crescent beach, sunsets. Vacation Rental License #VR-09-23. View Photos »
Virtual Tour »
TREEHOUSE
$5,000 monthly rental only 		Mile Marker 96, 1 bedroom, 1 bath, sleeps 4, dock, beach, and sunsets. View Photos »
OSPREY BAY
$5,000 weekly - $15,000 monthly 		Mile Marker 82.7, 4 bedrooms, 3 baths, sleeps 8-10, dockage, pool, spa, sunsets. View Photos »
BONEFISH BAY HOUSE
$6,000 weekly - $20,000 monthly		 Mile Marker 75. Four bedrooms/four 1/2 baths and two car garage. There are two bedrooms located on the first floor and two bedrooms located on the second floor. Sleeps up to 8. View Photos » YouTube »
SNOOK COTTAGE
AT BONEFISH BAY
$5,500 weekly - $16,500 monthly
 Mile Marker 75. Four bedrooms/four ½ baths and two car garage. There are two bedrooms located on the first floor and two bedrooms located on the second floor. Sleeps up to 8. #VR-09-59 View Photos » YouTube »
TARPON COTTAGE
AT BONEFISH BAY
$5,000 weekly - $15,000 monthly
Off Season: Call for rates 		Mile Marker 75. Four bedrooms/four ½ baths and two car garage. There are two bedrooms located on the first floor and two bedrooms located on the second floor. Sleeps up to 8. #VR-09-43 View Photos » YouTube »
LA JOLLA
$2,500 - $3,000 weekly
$7,500 - $9,000 monthly		 Three bedroom/three bath. Sleeps 6. Located in central Islamorada. Shared pool. Within walking distance to shopping and restaurants. Bayfront, dockage and sunsets. View Photos »

Florida Keys Condos, Townhomes & Flats
SAND PEBBLES
$4,000 monthly
Call for longer term rate		 Mile Marker 80. 2 bedrooms, 2 baths, sleeps 4. Stunning sunsets from this well maintained condo. Balconies in master bedroom & living area. This friendly 16 unit complex features pool/hot tub, BBQ area, chickee hut and views, views, views!
 Unit 105 - View Photos » YouTube »
Unit 303 - View Photos » YouTube »
OCEAN HARBOR K23
$5,000 monthly 		Mile marker 88. Enjoy the oceanview from this 2 bedroom, 2 bath condo that sleeps 4 in an ocean front, gated community with many amenities to include beach, heated pool, Jacuzzi, deep water dockage. View Photos »
BAY HARBOUR
$2,250 weekly - $6,700 monthly 		Mile Marker 74. 2 bedroom/ 2.5 Bath. Pool, Tennis Courts, Luxury Tommy Bahama-Style Furnishings. Vacation Rental License #VR-09-94. View Photos »
VILLA BLEU
$2,400 monthly 		Mile Marker 81, One bedroom/one bath cottage. Sleeps 2-4. Located in the heart of Islamorada. Within walking distance to dining and shopping. Prime Location! Virtual Tour »
View Photos »
LITTLE HIBISCUS
$2,400 monthly 		Mile Marker 81. One bedroom/one bath cottage. Sleeps 2-4. Located in the heart of Islamorada. Within walking distance to dining and shopping. Prime Location! Virtual Tour »
MAISON MATECUMBE
$3,000 weekly - $9,000 monthly 		Unit #301
Marker 81, 3 bedrooms, 2 baths, sleeps 6,
pool, sandy beach. Vacation Rental
License #VR09-112.
Unit #304
Mile Marker 81, 3 bedrooms, 3 baths, 2 stories sleeps 6, pool, sandy beach. Vacation Rental
License #VR-09-112		 Unit 301 - View Photos » Unit 304 - View Photos »
Virtual Tour »
CAPTAINS QUARTERS - 4 PLEX
$1,190 weekly - $4,250 monthly 		Mile Marker 81.
Two bedroom/one bath $4,250 monthly
One bedroom/one bath $1,190 weekly - $3,250 monthly
Sleeps 4-6. Dockage, Wireless Internet, New A/C.		 View Photos »
Virtual Tour »
OCEAN POINTE
$1,200 weekly - $3,200 monthly 		Mile Marker 92.5, 2 bedroom, 2 baths, sleeps 5. Amenities include: Private sandy beach, Heated Swimming pool - Jr Olympic Size, Bar/Lounge, Gated Community/Security Guard, Barbecue Grill(s), Picnic area, Internet access in public areas - complimentary, Internet access - wireless, Cafe, Spa tub, Tennis, Dockage/reservation required. View Photos »
ANGLER'S REEF VILLAGE
Oceanside, Windley Key,
Islamorada
$1,800 - $4,000 weekly
$4,500 - $7,500 monthly		 MM 85. Beautiful ocean and garden views from these island-style detached villas. Nestled amidst quaint streets and walking paths, their design takes inspiration from Native Conch and Key West themes. Swimming pool and deep water dockage make these an angler’s paradise and a family playground.
Unit 110: 2 king beds, 2.5 baths.
Unit 127: 1 king & 2 queen beds, 2.5 baths.
Unit 148: 2 bedrooms – 1 king & 2 queen beds, 2.5 baths. Vacation Rental Lic # VR-148
Unit 149: 2 bedrooms – 1 king & 2 queen beds, 2.5 baths. Vacation Rental Lic # VR-164
Unit 150: 1 king & 2 queen beds, 2.5 baths.




Unit 110 - View Photos » Unit 127 - View Photos » Unit 148 - View Photos » Unit 149 - View Photos » Unit 150 - View Photos » You Tube

Lagoons, Canals & Waterways In The Florida Keys

THE GATEHOUSE
$15,000 monthly		 Mile Marker 74.5. Three bedroom, 2 bath upstairs. One bedroom, one bath downstairs. Pool and dockage. Sleeps 8. View Photos »
PELICAN LANDINGS
$2,000 weekly - $6,000 monthly 		Mile Marker 74. Two bedroom/two baths. Sleeps 4. Lagoon front with dockage. Less than two football fields away from the Florida Bay! View Photos »
LITTLE CONCH HOUSE
$5,500 monthly 		Mile Marker 87. Adorable two bedroom/two baths. 75' of dockage on large lagoon with direct access to Ocean and minutes from the Bay. View Photos »
SEA VIEW
$3,600 monthly 		Mile Marker 75. One bedroom/one bath. Hot tub, deep water dockage and nicely furnished. Sleeps 2. View Photos »
PORT ANTIGUA
$9,000 monthly 		Mile Marker 74. Three bedroom/three bath with game room. Sleeps 8. Deep water dockage, pool and luxuriously furnished. 3 month rental. View Photos »

Virtual Tour »
BALI BAY
$3,600 weekly - $10,000 monthly 		Mile Marker 74.5, 4 bedrooms, 3 baths, sleeps 8-10, heated pool and dockage. Vacation Rental License #VR-09-84. View Photos »
Virtual Tour »
BAREFOOT ELEGANCE
$24,750 monthly 		Mile Marker 75, 5 bedrooms, 4 baths, sleeps 10, luxurious, heated pool, deep water dockage. Boathouse with slip. View Photos »
Virtual Tour »
MIN FLICKA
$6,500 monthly		 Mile Marker 89. Spacious Five bedroom home, three bath home located on Plantation Key. Sleeps 10. Heated pool, deep water dockage, tiki hut and large exterior screened porch View Photos »
CANE DOC'S PLACE
$7,500 monthly		 Mile Marker 91. 4 Bedrooms and 2 baths. Sleeps 8. Located directly on Tavernier Creek with deep water dockage and easy ocean and bay access. Three story home on 1 1/2 lots. Cut-in boat slip and large boat lift. Beautiful view from family room and master bedroom. Mature landscaping, garage, gated paver driveway. View Photos »

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