81610 Overseas Highway
Islamorada, Florida Keys 33036
Phone: (305) 664-9166
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Islamorada Vacation Rentals

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... each bedroom upstairs has a king bed. Open living room and kitchen with oceanviews. Private downstairs apartment with kitchen, 2 bedrooms and 1 bath...2 queen beds and 1 king. Offered @ $3000 weekly and $8000 monthly.  VR-008

Enjoy spectacular sunrises daily with endless ocean views from this spacious and comfortable 5 bedroom Islamorada beach house. The upstairs offers generous living with open kitchen, living and dining overlooking the Atlantic.  Top floor living also includes an oceanfront king master bedroom, an oceanfront queen bedroom and a third queen guest  bedroom. While the downstairs accommodates additional guests with 2 separate "on the beach"  ocean queen bedroom suites with living, dining and kitchenette. Sun,sand and sea...... The only thing missing for the perfect beach holiday is you!  Offered monthly @ $12,500.

Beautiful Bay Harbor 2 bedroom/2.5 bath luxury condo located in Islamorada. Fully equipped kitchen and open living room which extends to your own screen porch. Both bedrooms have private bathrooms. Set-back ocean views overlooking the lagoon with boat dockage convenient to deep sea ocean and backcountry/ bay fishing. Relax at he pool or play a game of tennis if you prefer. Less than one mile to Anne's Beach and 10 minutes away from dining, shopping, attractions and all the best of Islamorada. Offered weekly $1,950 (20% increase on holidays for the weeklky rate) - Monthly @ $7,500.  VR-304

This Luxurious 3 bedroom Bay Harbor unit offers the perfect Florida Keys vacation experience. Lovely views of the lagoon can be enjoyed from the full length screened balcony while boat dockage just outside the unit provides quick access for off-shore sport fishing or backcountry game fishing in the bay. Beach access is available within one mile of the property. Beautifully appointed for leisure elegance, this lovely unit leaves nothing to be desired. Offered weekly @ $3,000 and monthly @ $8,000  VR-201

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.

Gorgeous views from our Bonefish Flats Beach House... every morning a new sunrise! Truly the quintessential home for island living. Completely remodeled interior and furnished with a designer's eye. The perfect way to enjoy Islamorada all year long. The home features 1 king main floor ensuite with walk-in shower and sliding doors opening directly to your oceanfront balcony. Your second main floor ensuite has a queen bed with completely remodeled bath. The home features a separate ground level queen ensuite opening directly onto the beach. The home is offered monthly for $10,700

Breezy Point is the quintesssential beach house! This oceanfront 2 bedroom 2 bath home is located on Islamorada's Lower Matecumbe Key. The master ensuite bedroom has 1 king and 1 twin bed and the guest room has 2 queen beds.. Both master and guest suites are equally roomy and both boosts gorgeous ocean views  Wide ope views from your patio while relaxing at the pool.  Patio furniture and gas grille makes outside dining the perfect choice while visiting Breezy Point. The property has a peninsula that stretches out into the ocean nearly 100 yards. Great fishing from the pier and dockage for your boat along the west side of the peninsula. Super location for paddle boarding and kayaying. Great home for families or a couple retreat. Offered weekly for $3000 and monthly for $10,000.

Beautiful bayfront pool property with boat dockage is located in the heart of Islamorada within walking distance to the best of the Florida Keys including shopping, dining and attractions. The private gated property includes a 3 bedroom, 1 bath Key West style main house and 1 bedroom, 1 bath cozy guest cottage. The natural saline filtration swimming pool and hot tub offers soft and silky,chlorine free water with spectaular Florida Bay sunsets as a backdrop to the ultimate in relaxation while the private poolside tiki hut sets the tone for many happy hours.  Enjoy great fishing, swimming and snorkeling right off the dock or launch the kayaks and paddleboards for your own backcountry excursion. Florida Bay is the angler's choice for rolling with the Tarpon and stalking the legendary and elusive grey ghost that is the Bonefish. Convenient bay to ocean access is a short trip to the splendor of the only living tropical reef in the continental US and the deepwater Gulfstream for sportsfising excitement of Sailfish, Tuna, Mahi and more. The Buttertfly Haven vacation experience will leave you exhausted from the best time ever!  And the desire to return ASAP. Offered weekly @ $3950  and monthly $13,825. VR-100

Adventure awaits you at this secluded unique 2 bedroom and 2 bath 60' 1948 Chris Craft "houseboat". Situated on 4 acres with it's own 300' private white sandy beach. Enjoy all the fun of boating while staying high and dry. Bird watchers will be delighted gazing at 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.  Enjoy a peaceful paddle on the kayak or cruise the bikes around town. Offered weekly for $2200 and monthly for $5800.

Enjoy great boating with direct ocean access to Alligator Reef from this 2 bedroom/ 2 bath canalfront stilt home. Location also provides convenient crossover to Florida Bay via Channels 2 and 5. Split floor plan offers space and privacy with newly remodeled full baths for each bedroom. Offered monthly for $3900.

The dream vacation awaits at this spectacular bay front 8 bedroom estate property located on Grassy Key. Plenty of room for everyone with 3 ocean king suites and one bedroom beachside bungalow in the main house, the three bedroom guest house and the private one bedroom cabana suite. The open floor plan with gourmet kitchen, living and dining offers leisure living overlooking Florida Bay while the screened porches are stylishly appointed for lounging and comfort. The open air grill terrace enhances outdoor dining with never ending bay views. Whether you are entertaining with family and friends or for business and pleasure Dream Bay provides a private resort setting that leaves nothing to be desired. Offered weekly @ $15,500 with 20% additional for all holiday weeks Monthly rate available upon request.

Beautifully updated  Exceutive Bay 2 bedroom/ 2 bath condominium located in the Village of Islamorada.  Great bayfront location with white sand beach, swimming pool, tennis courts, and clubhouse.  Conveniently located close to shopping center with grocery store, movie cinema, restaurants, shopping, fishing and attractions and also right next door  to the Founder's Bayfront park for walking trails, sunset beach and more. The unit is updated with tile floors and modern kitchen with granite countertops and stainless appliances.  The townhouse provides ground level kitchen, living, dining and full bath at entrance level while the two bedrooms are located upstairs with a second full bath. The dining area steps out onto a garden patio surrounded with tropical foliage. The living area is spaciously furnished with modern leather decor and large flat screen TV. Offered monthly for $3,500.

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 $4,500 weekly $15,000 for a 4 week stay.  VR-047

Upscale newly remodeled Islamorada pool home located on Florida Bay provides the perfect vacation destination. This 3 bedroom/ 3 bath home features polished marble tile floors, granite kitchen countertops and a private bath for each bedroom with generous sized european style marble and glass showers. Great location in the center of Islamorada next to the Lorelei is convenient to the best shopping, dining, fishing and local attractions. There is also boat dockage to complete the perfect package. Whether you are coming to tease the tarpon and stalk the elusive gray ghost or just to bathe yourself in the tranqulity of sunsets over Florida Bay, this home is sure to please everyone in your party. Offered monthly @ $10,500. Call for offseason rates.  VR-219

Spacious 3 bedroom end unit condo in prestigious Ocean Harbor with full length screened balcony overlooking the ocean. Amenities include boat dockage with immediate ocean access and convenient access to Florida Bay. Also, the complex features an oceanfront fitness center and clubhouse, swimming pool, hot tub, and tennis courts. Located in Islamorada, the Sportsfishing capital of the world, in close proximity to the best dining, shopping, and entertaiment. This unit is offered monthy @ $6,500.

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.

 This charming beach house is a hidden gem located right in the heart of Islamorada. Expansive oceanviews surround you while relaxing among the palm trees and the ever changing colors of the beautiful Atlantic Ocean. The cottage has a very unique set up with separate living both up and downstairs. The downstairs living is comprised of one bedroom and one bath along with the kitchen and living area. While the upstairs has two bedrooms and one bath... boosting oceanviews from all three bedrooms. The pier gives you hours of enjoyment... launch the paddle board or kayak for a peaceful paddle through the blue waters. The home is centrally located which enables you to bike all around town. Offered monthly $6,500.

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 $9950 or monthly for $29,500. Holidays are subject to a 20% rate increase.  VR-082

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 $10,000 monthly.

Leila's Beach House ...The perfect Islamorada beachfront home... centrally located right in the heart of Islamorada. Gorgeous sunrise views all throughout the home. Lounge on the oversized deck and enjoy the colors of the ocean. The house is comprised of 2 bedrooms on the main level and a master en suite secluded upstairs. Relax at your private oceanfront pool. Paddle boards, hobbie cat and bikes are included for your enjoymnet at the beach house

Fabulous Bayfront property with boat dockage in the most sought after location in Islamorada. Rental options include a duplex with 2 bedrooms and 2 baths per unit. Also available is a large separate 2 bedroom/ 2 bath cottage. Units may be rented separately or all together if available for a total of 6 Bedrooms / 6 Baths for entire one acre property . Duplex available Weekly $2500 each unit and monthly $7500 each unit. Cottage also available weekly $2500 or monthly $7500 Unit A -VR-084, Unit B- VR-085, Unit C- VR-086

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.  VR-077

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 with renovated kitchen and granite countertops 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 @ $9,000.  VR-124

Islamorada's exclusive Maison Matecumbe, comprised of only 9 units, offers privacy and luxury in the heart of Islamorada. This impeccably maintained 3 bedroom/3 bath townhouse with open living, kitchen and dining flows into the screened balcony, completely furnished to extend indoor/outdoor living, enhanced with picturesque ocean views and panoramic sunrises. The upstairs king master with ensuite bath and spa tub, wet bar and open balcony with forever ocean views provides the perfect setting for sunset cocktails and evening stargazing. With a natural white sand beach and large tropical landscaped swimming pool this well appointed townhousee leaves nothing to be desired. Conveniently located in close proximity to all the best of Islamorada. Offered weekly @ $3300 and monthly @ $9900.  VR-021

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.   VR-111

Gorgeous bayviews from this 3 bedroom 3 bath Port Antigua bayfront home. Beautifully furnished with just the right touches. Fully equipped kitchen for all the chefs in the family... bayviews while your cooking! White sandy beach for swimming. 90' of protected dockage with running water and fish cleaning station. Offered @ $8800 a month.

Beautifully appointed bayfront property located on private road in the heart of Islamorada. This new home offers bayfront living at its best with heated swimming pool, bay views, boat dockage and great swimming in the crystal bay waters. Also great boating with convenient ocean access. The spacious gourmet kitchen completes this home to offer the ultimate Fl Keys vacation. Offered monthly @ $20,000. 20% rate increase for holidays.

"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 $6,000.

Beautifully furnished canalfront home in Key Largo.Three bedrooms and 2 bath upstairs with a seperate 1 bedroom 2 bath downstairs apartment. Superb dockage with easy ocean access. Outside seating overlooking the swimming pool along with outside dining area. Great family home with all the comforts. Offered monthly for $6750

Newly renovated Palms unit on the 4th floor. Located oceanfront in Islamorda. Nicely decorated with an Island flare. The complex offers gorgeous views and heated swimming pool. Two bedrooms and 2 baths with open living room, kitchen and dining room. Beautiful oceanviews from your private patio. Monthly rates $3300

Enjoy "Old Florida " charm in this bayfront 3 bedroom 1.5 bath conch cottage located in the heart of Islamorada on two private acres with luscious Mangos and Key Limes in season. Dockage available in the protected boat basin with convenient bay to ocean access. Secluded swimming / snorkeling in the bay with outdoor freshwater shower. Bayfront Tiki for island style relaxation and enjoying spectacular Florida Keys sunsets. The perfect escape plan for a vacation getaway that is sure to refresh and renew the weary soul. Offered monthly $6,000.

Refreshing new construction... bayfront home with everything that you have been looking for. Professionally designed and decorated to appeal to everyone's rental preferences and priorities. This Gulf front estate home offers 4 bedrooms and 4.5 baths. A perfect destination for the discerning traveler. All four bedrooms have private large bathrooms. Huge master bath with a sauna, gorgeous glass shower and high end jetted tub. State of the art TV's and electronics. Open living room, sitting room, dining and gourmet kitchen to enjoy family and friends. The 180 degree water views from the house are exquisite! Large open porches allow for sunset dinners and day long views of the gulf waters. Enjoy the fun of the shuffle board table, ping pong and the swimming pool.The lushly landscaped property is completely fenced in with a private electric gate. Protected dockage and beach area makes for the perfect outdoor entertainment . Offered weekly for $8000  VR-067

Prime Port Antigua location with boat dockage and immediate bay access. The full length screend patio overlooking the Parmallee Plantation is a tranquil place to while away the time watching the many pelicans, ospreys, manatees and other wildlife that grace this peaceful location..... or hop on your boat and be one minute from spectacular sunsets and worldclass fishing. The homeowner's association hosts one of the best natural white sand bayfront beaches in the Upper Keys. Convenient ocean access is available through the Channel 5 Bridge. This 3 Bedroom/ 3 bath stilt home offered monthly $4,000.

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 $13,500.

Whimsical open bayfront home transforms you instantly into vacation mode. This 4 bedroom 3 bath home offers 3 bedrooms and 2 baths upstairs and a separate 1 bedroom and 1 bath apartment downstairs. Enjoy the gorgeous bay waters and beautiful sunset views. Boaters paradise with protected deep water dockage. Offered monthly @ $8000.

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.  VR-102

Year round sunsets at "Sunset Cay"... Gorgeous bayviews from this 4 bedroom 3 bath bayfront home located in the quiet neighborhood of Indian Waterways. Upstairs has a large open living room and dining room. The kitchen has been recently updated with stainless appliances. Two bedrooms and 2 baths complete the upstairs. Private downstairs separate apartment with full kitchen, dining area, 2 bedrooms and 1 bath. The upstairs and downstairs both have screened porches directly on the bay. Great boat dockage and boat ramp located on the property. Offered monthly @ $7000

Just what you were in search of! Five bedrooms / four bath bayfront home. Expansive bayviews and sunsets for your enjoyment. This fabulous home will set the tone for a memorable vacation. Perfect family home to keep the kids occupied and the adults relaxed and happy. Bayfront swimming pool to spend the warm days by. If saltwater is your calling there is outstanding swimming and snorkeling directly from the dock. Offered @ $12,000 monthly.

Enjoy great boating, fishing and swimming from this three bedroom/ two bath ground level Venetian Shores canal home located on Snake Creek with immediate ocean to bay boating. Convenient to Founder's Park for access to the bayfront beach and olympic-size swimming pool. Offered monthly @ $5,500.

Spacious and comfortable Venetian Shores home includes deepwater boat dockage in the homeowner's marina. Full length screened porch offers outside dining and lounging overlooking the canal. Plenty of space to stretch out with three bedrooms/ two baths upstairs and two bedrooms and one bath downstairs. Conveniently located to Founder's Park for bayfront beach access, tennis courts and olympic-size swimming pool. Offered monthly @$5500.

Villa Morada Bayfront perfection aptly describes this exquisite Islamorada bayfront home which offers comfort and luxury overlooking Florida Bay. Five spacious bedrooms each with ensuite bath provide plenty of privacy for everyone. All bedrooms have their own television and there is also a theatre set media room for group movie viewing complete with a playstation for the gamers. The well equipped gourmet kitchen is set up to serve casual and formal meals with ease whether dining inside or out on the porch overlooking the bay. Florida Bay offers excellent backcountry game fishing and also convenient ocean access for deep sea sport fishing. The crystal bay waters are ideal for swimming, snorkeling, and lobster hunting in season. The downstairs lounge extends gracious living to the outdoors with a shaded living, dining and grilling area poolside, complete with air hockey. foosball and a pool table. With swimming pool, hot tub, beach, kayaks, and boat dockage to accommodate up to a 40 ft boat, fun in the sun is assured. Truly, no detail is left unattended. This perfect home, set against the backdrop of a spectacular Florida Keys sunset is sure to provide a memorable vacation experience that will last a lifetime........or, until your next visit. Please call for rates and availability.

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