Islamorada Rentals, Key Largo Rentals &
Florida Keys Vacation Rentals

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Your Islamorada rental and Key Largo rental search starts 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 link to paradise, and we are here to help you explore your options for a dream Florida Keys vacation.

Escape to your Islamorada rental retreat or Key Largo vacation hideaway and enjoy the island life. Whether your 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 vacation planning through your stay at one of our Key Largo 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 Keys.

Our Florida Keys 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. Or call us at 305-664-3333.

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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
	OCEAN PIER $12,000 monthly	MM 75. Great ocean views from this 3/3 gated Islamorada home with a private sandy beach, new heated pool, 360 ft. pier with boat dockage & davits. It is a 2/2 up with 1/1 guest quarters down. Nicely landscaped through out.	View Photos »
	ATLANTIC POINT $19,000 monthly	Mile Marker 87. Enjoy this 4 bedroom/3 bath home, sleeps 8. Has a heated pool & Jacuzzi, deep water dockage for up to a 35' vessel, poolside cabana & kitchen. It is an oceanfront home with a very natural shallow shoreline known best for flats fishing!	View Photos »
	LA PLAYA $10,000 weekly - $30,000 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	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 » Virtual Tour »
	GREEN TURTLE BEACH $8,500 weekly - $29,500 monthly	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	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 »
	COCONUT SOUTHERN $5,000 weekly -$14,000 monthly	Mile Marker 75, Almost an acre. Quintessential beach cottage with a beach, pool and dock. A rare find! 2 bedrooms 2 bathrooms. 1 king 2 queens.	View Photos »
	PEACEFUL PALMS $4,750 weekly	Mile Marker 81.5, 3 bedrooms, 3 baths, sleeps 6-8, sandy beach, pool, sunrises. 4 acres. Quiet and private. Vacation Rental License #VR-09-104.	View Photos » Virtual Tour »
	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	Mile Marker 77, 3 bedrooms, 3 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 $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 »
	BALI HIGH $30,000 monthly	Main house offers two master suites with a split floor plan. Adjoining children's room off one master suite. Guest house offers two guest rooms with sitting area and kitchenette. Maid's Quarters with daily maid service. 200 ft of oceanfront with 5ft controlling depth at dock.	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.	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 $5,500 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 »
	SOUTH BEACH $7,500 monthly	Mile Marker 74.5, 3 bedrooms, 2 baths, sleeps 6-8, open water, jacuzzi, dockage, beautiful sunsets.	View Photos » Virtual Tour »
	VILLA VIKING $6,000 monthly	Mile Marker 87. Bayfront ground level home, 3 bedrooms, 2 baths. Possible 4th bedroom available (extra fee), handicap access, shared community pool, boat slip and boat ramp.	View Photos »
	MARLIN COTTAGE AT BONEFISH BAY $5,000 weekly - $15,000 monthly Off Season: Call for rates Mile Marker 75. Four bedrooms, four ½ baths. Exquisite bay views with sunsets! Private pool, Jacuzzi, Gourmet kitchen, luxuriously furnished, sandy beach, dockage and tennis courts. Exclusive private living at its finest! Sleeps 8-10. Vacation Rental License #VR-09-128.		View Photos »
	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 »
	STARFISH COTTAGE AT BONEFISH BAY $7,000 weekly - $21,000 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-09-60		View Photos »
	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 »
	LA JOLLA $2,500 weekly	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
	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 - #301 - ONLY 9 UNITS $3,000 weekly - $9,000 monthly	Mile Marker 81, 3 bedrooms, 2 baths, sleeps 6, pool, sandy beach. Vacation Rental License #VR09-112.	View Photos »
	MAISON MATECUMBE - #304 - ONLY 9 UNITS $3,000 weekly - $9,000 monthly	Mile Marker 81, 3 bedrooms, 3 baths, 2 stories sleeps 6, pool, sandy beach. Vacation Rental License #VR-09-112.	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. Click here to visit our website.	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 » Virtual Tour »
	THE COVE - SOUTH/NORTH $2,400 monthly	Best priced unit on the island! Tastefully refurbished with granite & stainless on very large parcel.	View Photos »
	THE PALMS $3,500 monthly	Two bedroom/two bath. Sleeps 4. Mile Marker 80, Ocean side. Ocean front pool and Jacuzzi.	View Photos »
LAGOONS, CANALS & WATERWAYS IN THE FLORIDA KEYS
	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 »
	VENETIAN CREEK $13,500 monthly	Mile Marker 86. Two bedroom and two bath upstairs. Separate entrance to two additional bedrooms and one bath downstairs. Deep Dockage, Ocean and Bay access, pool and Jacuzzi. Sleeps 10-12.	View Photos » Virtual Tour »
	SNAPFISH $2,500 weekly - $4,000 monthly	Mile Marker 91. Three bedroom/two bath stilt home located in Plantation Key Colony. Dockage, Jacuzzi, chikee hut, outdoor kitchen and fish cleaning station. Sleeps 6.	View Photos »
	VILLA MADEIRA $5,500 monthly	Expansive, elegant, three story Waterfront villa! Includes 3/3 beautiful, innovative bedrooms and bathrooms! Deep water dock with davits. Perfect family retreat.	View Photos »

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Islamorada Rentals, Key Largo Rentals & Florida Keys Vacation Rentals

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

Islamorada Rentals, Key Largo Rentals &
Florida Keys Vacation Rentals