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You are currently viewing ALL Vacation Rentals in Islamorada and Key Largo

For more information on any of the vacation homes below, place a check in the box next to the homes you are interested in & complete the form at the bottom of the page.

Call us at (305) 396-9002 or toll free (888) 764-8228



Vacation Rental

Alligator Reef and Cottage

US $5,500-7,400/Weekly




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Village of Islamorada License #

Information


Islamorada, Florida
Oceanfront
Heated Pool
Pet Friendly
7 br, 5 BA


Located at Mile Marker 84, in Islamorada. Spacious enough for 14 guests, or cozy for 8 guests! Main House 4 bedrooms, 3 BAths plus a separate 3 bedroom 2 BAth cottage. Main house may also be rented alone. This Beautiful oceanfront estate includes: internet, heated pool, observation pier, kayak, putting green and horseshoes for a great family or corporate retreat.

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Aquazul

US $5,000-5,400/Weekly





Aguazul Photo


Village of Islamorada License #

Islamorada, Florida
Oceanfront
Heated Pool
Deep Water Dockage
4 br, 4 BA


Located at Mile Marker 87, in Islamorada. Aguzual is simply a pristine Florida Keys Vacation Rental! With 4 bedrooms, 4 BAths, sleeps 6-8. Captivating oceanfront home with heated pool and deepwater dock. Amenities include 2 master suites and 2 kitchen areas. Spectacular sunrises from the unique third story terrace. High speed internet


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Bay Marche'

US $6,000-7,000/Weekly




Bay Marche' Photo


Islamorada, Florida
Bay Front
Heated Pool
Deep Water Dockage
5 br, 4 BA


Located at Mile Marker 76. Spectacular panoramic views of the Florida Bay. This five bedroom home with open air BAlconies allows for the best Bay views in the Keys. Comfortably sleeps 8-10; Upstairs has huge living room, dining room, kitchen area with liberal picture windows to capture the best of Keys waterfront views. Expansive property with beach area, large heated pool (fenced) and dockage for large boats. Additional sitting area in the downstairs gives easy access to the pool and beachfront. Well appointed property suits large families and couples looking for that escape to paradise, in this Florida Keys Vacation Rental.
Village of Islamorada License #


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Calypso

US $3,450-3,850/Weekly




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Village of Islamorada License #

Islamorada, Florida (Tavernier)
Oceanfront
Heated Pool
Deep Water Dockage
3 br, 3 BA


Located at Mile Marker 88.7 This PET FRIENDLY unique 3 bedroom, 3 BAth, oceanfront homes sleeps 8-10. Gated for privacy. Spectacular open-water views. Beautiful heated pool. Ample 350 foot dock with stairs attached to a floating platform for direct access to sandy ocean bottom. Bright and Cheery décor! High-speed internet



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Casa Eroici

US $6,500-9,500/Weekly






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Village of Islamorada License #

Islamorada, Florida
Oceanfront
Heated Pool with Spa
Deep Water Dockage
4 br, 4.5 BA



Casa Eroici is a 4 Bedroom 4½ Bath Oceanfront Estate, nestled on 2 acres of gated landscaped grounds on Millionaires Row in Islamorada. Beach with a fabulous Pool with Spa, Sun Deck, and 2 Gazebos overlooking the Crystal Blue Waters of the Atlantic Ocean. The 300-foot Dock is equipped with a Cleaning Station for all your boating and fishing needs

Casa Grande

US $7,500-8,000/Weekly






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Key Largo, Florida
Canal/Oceanfront
Heated Pool
Deep Water Dockage
6 br, 6.5 BA

Located at Mile Marker 92. Extravagance is the theme throughout this spectacular six bedroom home. Custom furnishings only add to the opulence of this Keys masterpiece. This unique home offers oceanviews that are unparalleled from the spacious BAlconies on each level. Amenities abound from the gourmet kitchen and private elevator to the decadent decor. Largo private pool and Jacuzzi with 90 feet of seawall dockage allow for leisurely sunning after a day of offshore fishing only the Keys can offer. Located at the end of an open canal, with direct ocean access you truly will want to make this your ONLY vacation destination this year! 3 master suites, elevator, high speed internet, privacy afforded.

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Casa Venetia

US $6,500-7,500 / Monthly




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Islamorada, Florida
Canalfront
Pool
3 BR, 3 BA



Getting ready to winter with us in the Florida Keys> Casa Venetia has 3 bedrooms & 3 BAthrooms. It accommodates 6 people, and sits in the lovely and quiet residential neighborhood of Plantation Key. This contemporary house has been totally and completely renovated inside and out. Outside, you will enjoy our covered lounge, large tropically landscaped deck, pool and 100’ dock which all overlook the wide canal. You may dock your boat, and get immediate Ocean access through Snake Creek Bridge

Coral Cove

US $2,500- 3,400/Weekly





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Village of Islamorada License #

Islamorada, Florida
100 yards from Oceanfront
Shared Pool
Shared Deep Water Dockage
3 BR, 3 BA


Located at MM 81 This well appointed home includes 3 bedrooms, 3 BAths, sleeps 4-6. Coral Cove is an upscale plantation style home with great attention to detail. The private, gated community with shared heated pool and beach area just yards from the house. Located in the heart of Islamorada, making this vacation home close to restaurants and shopping. DSL is available. Flat screen TV's and DVDs in each room, plus a Bose entertainment system


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Deep Blue View

US $5,000-6,400/Weekly



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Village of Islamorada License #

Islamorada, Florida
Heated Pool
5 br, 3 BA



Located at Mile Marker 86.5 with 5 bedrooms, 3 BAths, this property sleeps 10-12. Gated estate home offers magnificent sunrises viewed from both 2nd and 3rd floor BAlconies. Plus sliding doors off the kitchen and add’l upstairs sitting area allow you to take in open ocean views throughout this home. Modern architecture with 3 levels - there is ample room for the whole group. Unique amenities include tiled floors heated pool, theatre room, screened porch with pool table, high speed internet. Nearby dockage available


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Dock of The Bay

US $2,600-3,000/Weekly



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Islamorada, Florida
Heated Pool
Deepwater Dockage
3 br, 3 BA



In Historic Layton, this bayfront property has pool, ample dockage and open waterviews. Three bedrooms and three baths provide perfect accommodation for family outing in the privacy of this bayfront home. Located at MM 69 this vacation rental lies between Islamorada and Marathon. Beautiful sunsets can be viewed from the expansive waterfront yard area with private tiki hut on the property; quiet and out of the way, this property is the perfect getaway for that special couples outing or a small family affair.




Sunset Beach

US $3,700-4,500/Weekly



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Village of Islamorada License #

Islamorada, Florida
Beach
Dockage
5 br, 3 BA



Located at Mile Marker 74.5 with 5 bedrooms, 3 Baths, this property sleeps 10 - 12. This beautiful 3 level home sits on a private white sand beach and offers 40 feet of dockage for your boat! Sunset Beach is fully equipped with TV's in each room, two large plasma TV's and high-speed internet.


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Green Turtle

US $7,500-$8,500/Weekly



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Village of Islamorada License #

Islamorada, Florida
Private White Sandy Walk In Beach
Heated Pool & Jacuzzi
5 br, 8.5 BA


Located in the heart of Islamorada at MM 81.5, 5 bedrms, 8.5 BAths, sleeps 10-12. Spacious, private plantation-style estate home on 5 acres. Gated with grounds security. Two story with elevator and grand staircase. Heated pool and Jacuzzi, expansive white sandy beachfront. The best in Islamorada!! Spectacular open-water sunrise views. Upscale and unique in design.. Basketball court & tennis court, shared. High-speed internet. Combine with Green turtle 2 for a perfect family vacation or corporate retreat


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Green Turtle 2

US $7,500 - $8,500 / Weekly




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Village of Islamorada License #

Islamorada, Florida
Private White Sandy Walk In Beach
Heated Pool & Jacuzzi
4 br, 5 BA


Located at Mile Marker 81.5, adjacent to Green Turtle on private Green Turtle beach; one of the very few and very rare sandy walking beaches in the Florida Keys. Four master suites serve as sleeping accommodations with grand living room, library and open kitchen layout. This private estate home includes wrap around porches that run the length of the house, opening onto the expansive white, sandy walk-in beach. Gated heated pool and Jacuzzi area for children’s safety. High-speed internet, flat screens and Hi-tech Stereo system provide up-to-date electronics along with IPOD docks in every room. In the heart of Islamorada


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Largo Sound

US $7,000 - 10,500 / Weekly





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Key Largo, Florida
Heated Pool and Jacuzzi
Ample Deep Water Dockage
5 br, 5 BA



This executive estate home has been totally renovated inside. Ride the "private elevator" to one of 4 floors of entertaining areas! More than 7000 sq ft of luxury. Features include: New marble floors throughout. New luxury BAths. Huge terraces and wrap around BAlconies. Three (3) separate living areas. Newly furnished and custom decorated with modern furnishings for the guest who wants the best

Lighthouse

US $6,500-$7,500/Weekly





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Key largo, Florida
Excellent DeepWater Dockage
Historic Working Lighthouse
Heated Pool & Jacuzzi
6 br, 5 BA


Lighthouse Estate is an tranquil, exceptionally private 2 acres Ocean front estate located in a prestige area of Key Largo Florida. The Main Home features 2 master suites, spacious kitchen, and intimate living spaces. The Annex is a 3 bedroom 1 BAth cottage with an inviting living/TV area. The Historic Lighthouse features 2 cozy bedroom 1 BAth plus small kitchenette and sitting area. Outside the Light House you'll find a cozy sandy beach area overlooking the Basin, and the point. The Point is an approximate 10000 sq ft tiled deck with Bar/BBQ area and additional sitting areas. With over 500'of concrete seawall plus a 30x100 BOAT BASIN for your boat(s)

Little Bay
Islamorada, Florida
Excellent DeepWater Dockage
3 Seperate Cottages

Located at MM 82 This private estate compound boasts three residents. The main cottage, newly renovated, has large master with private BAth, glassed florida room surrounded by tropical foliage. Murphy bed and add’l BAth sleeps 4 comfortably. The duplex on the BAy front offers a 2/2 up and a 2/2 down. Sliding glass doors open onto wide porch areas to sit and watch the spectacular sunsets only the Florida Keys can offer. Private boat BAsin allows for ample deep water seawall dockage. Sunning area and tiki hut only add to the privacy this beautiful estate property has to offer.

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US $2,400/Per Cottage/Weekly


Village of Islamorada License #

Nautica
Islamorada, Florida
Bay Front
Heated Pool
Dockage
Privacy
4 br, 4 BA

Located at Mile Marker 82. Gated and private, this upscale home has large in ground heated pool and ample dockage with private boat BAsin! Three master suites with king beds as well as fourth with two twins allows for comfortable accommodations for 8. Conveniently located right in Islamorada this two story BAyfront property will appeal to guests wanted to experience the best of the Keys.

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US $6,000-7,000/weekly


Village of Islamorada License #

Ocean Terrace
Islamorada, Florida
Oceanfront
Oversized Jacuzzi
White Sandy walk-in Beach
Pet Friendly
3 br + den, 3 BA

Located at Mile Marker 81.5 this 3 bedrooms plus den sleeps 8-10. Gated with privacy well afforded with oceanfront, white-sandy beach make for perfect wade in bone fishing. Oversized outdoor Jacuzzi and kayak allow for great outdoor activity at this beachfront property. High-speed internet. Conveniently located in the downtown area, walking distance to shops, restaurants and local venues.


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US $3,950-4,200/Weekly


Village of Islamorada License #

Orange Blossom
Key Largo, Florida
Oceanfront
Brand New Deep Water Dockage
3 br, 3 BA

Located at Mile Marker 92, this gated stilt home offers 2 bedrooms, 2 BAths upstairs with one additional bedroom and BAth downstairs. Both have sleeper sofas. Sleeps 6 – 8 comfortably. Beautiful ocean views and deep water seawall dockage. Perfect for an offshore fishing retreat or kayakers haven. Oceanfront location with protected dockage allow you to enjoy kayaking out to the crystal clear waters surrounding Tavernier Key. Experience the peaceful serenity of the keys. High speed internet.

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US $2,500-3,500/Weekly

Ocean's End
Islamorada, Florida (Lower Matecumbe)
Oceanfront
Heated Pool
3 br, 3 BA

Located at Mile Marker 76.5 just south of downtown Islamorada with 3 bedrooms, 2 BAths, this private oceanfront home sleeps 6-8. With well appointed Key West Style, this oceanfront home offers a heated pool with open water ocean views along with the utmost privacy in quiet Lower Matecumbe. Great BAlconies off kitchen/dining offer terrific inside/outside living space. There is dockage at the nearby marina available. DSL available.


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US $3,500-3,900/Weekly


Village of Islamorada License #

Paradise Cove

US $6,900-10,500/Weekly




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Key Largo, Florida
Oceanfront
Heated Pool
Deep Water Dockage
3 br, 4 BA or 6 br, 4 BA

Paradise Cove of Key Largo offers 6 acres, gated, private, tropical lush landscaping with private marina and boat slip and two, breath taking, private homes. The oceanfront private estate with Sugar Palm, a 3 story brand new mansion with elevator and private pool with Jacuzzi. The exquisite guest house, Hibiscus, is located just 100 ft. From the main house. Yet, very private. The ultimate in privacy and luxury awaits you to enjoy this incredible vacation experience.

Sea Oats

US $6,900-8,000/Weekly





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Village of Islamorada License #

Islamorada, Florida
Oceanfront
White Sandy Beach
5 br, 5 BA



This fabulous oceanfront property sits on the most beautiful white sandy beachfront. Upscale and well appointed the five bedroom home includes 3 Master Suites with private BAth; patio doors opening onto oceanfront Balcony. 5000 square feet of living space that includes: 50 inch HD flat screen TV in living room Flat screens in all bedrooms.Privacy and/or blackout shades in all bedrooms Monitored alarm system throughout house Fully equipped Gourmet kitchen with Stainless GE Monogram appliances, ice maker, wine cooler, high top BAr, microwave, convection oven and more Commercial Sized Stainless Steel Propane BBQ grill on patio Central A/C and Heat Billiard table off living room Game room (Darts, Ping pong, FoosBAll) downstairs in lower level Located at MM 74.5 just minutes from downtown Islamorada.

Southern Diversion

US $7,000-8,000/weekly





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Village of Islamorada License #

Islamorada, Florida
Oceanfront
Heated Pool
150 foot Dock
2 acres of privacy
4 br + den, 3.5 BA

Located at Mile Marker 82.9. This private, gated home offers 4 large bedrooms plus den w/sleeper. 3.5 BAths, sleeps 13. Estate home on 2+ acres in downtown Islamorada, this is truly a diversion from the hustle and bustle life brings! So, relax and enjoy island living in lush landscaped grounds including: heated pool, private dock, white sandy beach area. Extensive amenities, including children's play area, High-speed internet and screened BAlcony to take in the incredible sunrise! Open air layout with great indoor/outdoor living space, this private home welcomes your family to the Keys.


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Seafarer

US $3,000-4,000/weekly





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Village of Islamorada License #



Islamorada, Florida
Bay Front
Heated Pool
Dockage
Privacy
5 br, 4 BA

Located right in Islamorada at Mile Marker 82, this gated property allows for family fun from sun up to sun down. Accommodates 8-10 comfortably. Boaters will love the nearby ocean/BAy access. Large BAyfront property with private boat BAsin, heated pool and five bedrooms. The open waterfront view can’t be beat and you can enjoy the best of Islamorada Sunsets in privacy at this beautiful BAyfront dream.
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San Roc
US $5,000 - 6,500/Weekly




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Village of Islamorada License #

Islamorada, Florida
Oceanfront
Beautiful Pool with Jacuzzi
Dockage
4 br, 3 BA

2.5 acres of naturally landscaped grounds in a premier area of Islamorada, Florida -- known as "Millionaires Row" are your hidden oasis at San Roc Estate. It has 4-Bedrooms (3 King Beds, 2 Twin Beds), and 3-Bathrooms, and is tropically decorated to complement its surroundings. Enjoy luxurious sunrises, ocean breezes and full moons from your own Private Beach

Tuscan Bay
US $15,000-20,000/weekly






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Village of Islamorada License #



Islamorada, Florida
Bay Front
Heated Pool
Dockage
Exclusive Privacy
9 br, 4 BA



Check Tuscan Bay Availability


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Imagine Rentals
81167 OverSeas Highway
Islamorada, FL 33036
Phone: +1 305-396-9002
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