Oceanfront Islamorada Vacation Rentals
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"Paradise Found" perfectly describes this gated 2 acre tropical estate home located in the heart of Islamorada with 250' of pristine white sand beach, swimming pool, tiki bar, and dockage. Plenty of room for everyone in the comfortable and spacious 3 bdr/3 bath main house with guest suite and separate one bedroom/ 1 bath guest cottage. The entire property to include main house and guest cottage for a total of four bedrooms and 4 baths is available weekly @ $6,000 or monthly @$19,000 or the 3 bedroom/ 3 bath main house only is available @ $5,000 per week or $16,000 per month. Holidays are subject to 20% rate increase. |
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This Islamorada home is the quintessential beach getaway. Full length oceanfront balcony offers the ideal place to relax and enjoy the endless oceanviews overlooking the beautiful white sand beach. Offshore waters provide great swimming & snorkelling. This 2 bedroom one bath home is offfered monthly for $10,000. |
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Key Breeze is just what you are looking for in a vacation home. This 3 bedroom 3 bath home is beautifully landscaped and captures what the Keys truely have to offer. The upstairs has 2 bedrooms and 2 bath and separate downstairs apartment has 1 bedroom and 1 bath. Lounge around the pool and enjoy the breeze off of the crystal clear waters. Easy access for either ocean or bay fishing. Offered weekly @ $3500 and $10,000 monthly. |
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Magnificent way to vacation! Gorgeous and private, gated 2 acre oceanfront estate home has left nothing to be desired. Contemporary furnishings and decor surround this 6000 sq. ft 5 bedroom and 5.5 bath prestigious home. Enjoy the expansive oceanviews from each of the 4 bedroom suites. Gourmet kitchen and dining room pours out into patio with only steps away from the infinity pool. Relax in your own piece of paradise with 360 degree luxury. Custom bathrooms with travertine tile and glass shower enclosures will give you the ultimate spa environment. Elevator with access to all levels. Private dock. Offered weekly @ $8800 and monthly $27,500. Holidays subject to an added 20% |
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Adventure awaits you at this secluded unique 2 bedroom and 2 bath "houseboat". Situated on it's own private white sandy beach. Enjoy all the fun of boating while staying high and dry. Bird watchers will be delighted watching the cranes and egrets at the water's edge. Conveniently located in the heart of Islamorada within walking distance to the best dining and shopping in the Village of Islamorada. The perfect setting for an adventurous getaway. Offered weekly for $1750 and monthly for $4750. |
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The ultimate island experience awaits you at Karapan I. This exquisite two story home is located on a pristine natural white sand beach with oceanviews that inspire relaxation. The 5 bedroom 5.5 bath home is ideally located in the heart of Islamorada within walking distance to all the favorite spots. Truly, this is the place to be for the perfect Keys vacation. Offered weekly for $8500 or monthly for $29,500. Holidays are subject to a 20% rate increase. |
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Maison Matecumbe Oceanview #302 Oceanviews and comfort from this upscale 3 bedroom/ 2 bath single level condo with West Indies decor ideally located in the heart of Islamorada. Tropical landscaped lagoon style pool offers a picturesque setting overlooking the ocean while comfortably furnished balconies extend outdoor living for dining and lounging. Spacious and well appointed this condo is sure to please the most discriminating of guests. Offered weekly $3250 and Monthly $8250. |
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The prettiest sunrises overlooking Islamorada's pristine Sunset Drive beach. This contemporary three bedroom and two bath oceanfront home is situated directly on the beach...perfectly appointed and the views are expansive. Enjoy swimming, kayaking and exploring right from the water's edge. The perfect beach for kite and wind surfing. A true white sandy beach in Islamorada! Offered monthly for $10,000. |
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Maison Matecumbe Poolside Townhome #304 Islamorada's exclusive Maison Matecumbe...this complex is comprised of only 9 units. Our poolside townhome has 3 bedrooms and 3 baths. There is an open living room kitchen and dining area. Enjoy the ocean breezes from your private screened porch. Maison has a heated swimming pool along with a hot tub and relaxing beach area with tiki hut. Weekly $3000 and monthly $9000. |
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Maison Matecumbe Poolside #301 Exclusive gated condominium of only nine units provide the perfect vacation location in the heart of Islamorada for the best of dining, shopping and attractions. Spacious floor plan offers comfortable living with two screened balconies just steps from the tropical landscaped swimming pool. Amenities also include a white sand sunning beach overlooking the Atlantic for spectacular sunrises. Offered weekly $3000 and Monthly $7500. |
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Islamorada beach home! Everyday a new sunrise! Gorgeous oceanviews from this 3 bedroom 2 bath home. Vaulted wood ceilings and charming decor. Shaded porches overlooking the Atlantic. Heated swimming pool. Ocean access for boating is available at the homeowner's boat ramp for in and out boating. Ample room for boat and trailer storage on the property. Offered @ $10,500 monthly and $3500 weekly. |
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This spacious oceanfront home and guest house offers a 4 bedroom 3 bath main house and 3 bedroom 2 bath guest house. Heated swimming pool, observation pier, putting green and horseshoes. The main house can be rented separately for $6,500 weekly. Entire 7 bedroom 5 bath main house and guest cottage offered for $ 7,500 weekly $22,000 monthly. |
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Maison Matecumbe Oceanfront Townhome #309 Panoramic views from the one and only oceanfront townhome in the exclusive Masion Matecumbe gated complex comprised of only 9 units. This upscale 3 bedroom 3 bath end unit has everything you will need for the perfect seaside getaway. The spacious accommodations offer expansive sunrises and refreshing ocean breezes from your private screen porch. Tropical landscaped pool is just steps outside your door. Amenities include a private master suite with wet bar,spa bath and ocean balcony. This unit is tastefully appointed and sure to please the most discriminating guests. Located in Islamorada Village Center at MM 80 convenient to all the best shopping, dining and fishings spots in town. This is definitely where you want to be for the ultimate Florida Keys experience. Offered weekly @ $3500 and monthly @ $8500. |
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Whimsical beach cottage with unobstructed oceanviews. This home offers 2 bedrooms and 2 bath upstairs with a separate 1 bedroom 1 bath downstairs apartment. Wraparound porch to enjoy your time here in the Keys. Gorgeous oceanviews and atlantic breezes are yours to treasure. Kayaks for exploring the shallow waters. Community boat ramp for your boating convenience. Offered monthly @ $6000. |
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Fun beach house right in the heart of Islamorada! Balconies overlooking the oceanfront plunge pool and sandy beach. Outside shower perfect for a day at the beach. This 3 bedroom 2.5 bath home with open living room and kitchen surrounds you with full oceanviews. Offered $4,200 weekly $12,600 monthly |
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Adorable oceanfront bungalow! Centrally located in Islamorada on 1 acre of private sandy beachfront. This home is just perfect for a couples get-a-way or for a small family vacation. A crowd pleaser for all anglers. Beautiful sunrise views every morning. Have fun fishing or just relaxing from the pier. Offered weekly at $2950 or monthly $7000. |
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Oceanfront home with 3 bedrooms and .3 baths. Upstairs has 2 bedrooms and 2 baths and downstairs is a separate 1 bedroom 1 bath apartment . Beautiful sunrises. Open kitchen and living room with wide open views. Offered $2,900 weekly $7500 monthly. |
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Escape from "it all" at Karapan II, an exceptional Island home located in the heart of Islamorada. The natural white sand beach and ocean views are the perfect setting for the ultimate relaxation experience. Vaulted ceilings and open floor plan provide a spacious and comfortable environment enhanced by the uniquely exotic furnishings. This 4 bedroom 4 bath home is within walking distance to the best Islamorada dining, shoppping and attractions. Once you visit this ideal vacation spot you will want to return again and again. Offered weekly for $8,500 and monthly for $27,500. |
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Oceanviews forever! This 5 bedroom/ 4 bath Islamorada home is situated on one of the Keys rare sugar sand barefoot beaches. Three master suites open onto the balcony overlooking the Atlantic for 180 degree oceanviews. This very well appointed open floor plan home features a gourmet kitchen and modern upscale baths. There is a game room with a billiard table, fooseball, darts and ping pong. Offered weekly $6,000 and monthly $20,000. |
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Adorable beach house with panoramic views of the Atlantic. Enjoy tropical breezes from the ooceanfront balcony. Property features a chickee hut, hammock, and oceanfront fishing dock. This beautifully furnished 3 bedroom 3 bath home with updated baths and a stylish Bistro kitchen sleeps six. Offered weekly $3,200 monthly $8,500. |
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Step out your door and onto the beach! Beautiful sunrises from this 4 bedroom 3 bath oceanfront home situated on a natural stretch of white sandy beach located in Islamorada. Upstairs is 2 bedrooms and 2 baths. Open living room and kitchen with oceanviews. Private downstairs apartment with kitchen, 2 bedrooms and 1 bath. Offered @ $3000 weekly and $8000 monthly. |
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Maison Matecumbe Oceanview Townhouse #306 This exlcusive Maison Matecumbe complex provides a private resort setting of only 9 units with spectacular oceanviews and amenities that will make this the ideal Florida Keys vacation destination. Ideally located in the heart of Islamorada where all the best fishing, dining, shopping and favorite spots are. This tastefully furnished unit is sure to provide the ultimate seaside escape. Amenities include spacious master suite with wet bar, private spa bath and ocean balcony. Available weekly @ $3,000 and monthly @ $8,500. |
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Lovely two bedroom oceanfront condominium on Plantation Key in Islamorada! Beautifully updated & comfortably furnished. Views of the Atlantic Ocean from every room! Offered monthly $3400 |
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Unobstructed oceanviews from this 2 bedroom 2 bath oceanfront condo. Updated unit. Swimming pool and tennis court. Centrally located for shopping or dining. Just minutes away from snorkeling, diving and fishing. $1300 weekly and $3950 monthly. |
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"All in One" package in this great 2 bedroom/ 2 Bath oceanfront Islamorada condo to include boat doockage, sunning beach, swimming pool, fitness center and tennis courts. Sprawling floor plan offers a spacious feel not often found in a condominium. Executive style master bedroom features a large bath with spa tub, separate step-in shower, dressing room and walk-in closet. Screened balcony overlooking the ocean provides spectacular sunrises and oceanviews. This upscale gated property is located at MM 88 for convenient access to shopping, dining and attractions. Available monthly for $5,000. |
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The perfect vacation experience can be found in this five star deluxe 4 bedroom/ 4.5 bath penthouse condominium. This unit is spacious and tastefully decorated with designer furnishings and a gourmet kitchen. The dining and living areas offer gorgeous ocean views overlooking the boat basin. There is also a rooftop sunning deck that allows for panoramic views and ultimate relaxation. Amenities inside the unit include a private sauna, steam room and media room while the upscale boutique condominium complex features a heated swimming pool, hot tub, clubhouse, and fitness center. Boaters will enjoy the boat dockage connveniently located right in front of the unit with ocean and bay access while beachcombers will love Sea Oats Beach located across the street from the unit. These accommodations are sure to delight the most descriminating of guests and will provide the ultimate experience for pampering and relaxation. Arrangements can be made for the adjoining unit to provide a total of 7 bedrooms and 7baths for large groups. The only thing missing here for the perfect vacation is you. The 4 Bedroom/ 4 bath unit is offered weekly for $6,500 or include adjoinng unit for a full 7 bedrooms/ 7 baths for $9,500 weekly. Please inquire for monthly rate. |
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Trendy island style 3 bedroom/3 bath condominium offers oceanviews, boat dockage and beach access across the street at Sea Oats Beach. Upscale boutique condo offers resort style living with heated swimming pool, hot tub and clubhouse. Offered weekly for $4,000. This unit can be adjoined to penthouse to provide a total of 7 bedrooms 7.5 baths available weekly for $9,500. Please inquire for monthly rate. |
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Beautifully appointed 3 bedroom/ 2.5 bath Islamorada condo offers great oceanviews overlooking the boat basin. Boat dockage providing ocean and bay acces is conveniently locted in front of the unit. Breachcombers will enjoy the white sand beaches located just across the street. There is a also a heated swimming pool, hot tub and club house. This vacation destination leaves nothing to be desired and is sure to please even the most discriminating guest. Offered weekly for $3500 and monthly $9000. |
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Elegant 2 bedroom/ 2.5 bath oceanview condo located in Islamorada. This tastefully appointed unit leaves nothing to be desired with boat dockage in front of the unit and access to the white sand beach across the street. This resort style complex is complete with a fitness center, luxury swimming pool, hot tub and clubhouse. Offered weekly for $2800 and monthly $8000. |
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Oceanview 2 bedroom/ 2.5 bath Islamorada condo offers stylish island living in a resort setting. The accommodations leave nothing to be desired with boat dockage, swimming pool, hot tub, clubhouse and fitness center. The gourmet kitchen and spa bath complete the package for the ultimate vacation experience. Offered weekly for $2800 and monthly $8000. |
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