Vacation Home Rentals By Owner In Islamorada, FL

Showing 365 Of 365 Vacation Rentals

$431.9

Islamorada's Premier Boating Neighborhood; Venetian Shores. A boaters paradise.

Islamorada, Florida, United States

Nestled within the serene surroundings of Islamorada, Florida, awaits a charming oasis at 116 Stromboli Drive. This single-family home, gracefully situated in the heart of one of Florida's most picturesque locations, invites you to embrace coastal living at its finest.brbrTucked away in the tranquil neighborhood of Islamorada, this residence offers the perfect blend of comfort, convenience, and coastal allure. Boasting an address that epitomizes the essence of tropical tranquility, 116 Stromboli Drive is not just a home; it's a retreat—a sanctuary where every day feels like a vacation.brbrStep inside this meticulously crafted abode and discover a spacious layout designed to accommodate modern living while exuding timeless charm. With three bedrooms and two bathrooms spread across approximately 1,728 square feet of thoughtfully designed living space, this residence offers ample room for relaxation and entertainment.brbrAs you enter, you are greeted by an ambiance of warmth and hospitality, characterized by an abundance of natural light that floods the interiors, accentuating the inviting atmosphere. The heart of the home lies within its open-concept living areas, where family and friends can gather effortlessly, creating memories to last a lifetime.brbrThe well-appointed kitchen, complete with contemporary appliances and ample cabinetry, beckons culinary enthusiasts to indulge their passions and create culinary masterpieces. Whether preparing a casual meal or hosting a festive gathering, this culinary haven is sure to inspire.brbrRetreat to the comfort of the private quarters, where tranquility reigns supreme. The spacious bedrooms provide a serene sanctuary to unwind after a long day, while the bathrooms offer a spa-like experience, inviting relaxation and rejuvenation.brbrBeyond the confines of the home, outdoor living takes center stage, courtesy of the expansive lot size of 7,000 square feet. Step outside to discover a lush tropical paradise, where verdant landscaping sets the stage for al fresco dining, leisurely strolls, or simply basking in the Florida sunshine.brbrConveniently located in the coveted ZIP code 33036, residents of 116 Stromboli Drive enjoy easy access to a plethora of amenities and attractions. From pristine beaches and water sports to shopping, dining, and entertainment, the best of Florida living is right at your fingertips.brbrWith its idyllic location, impeccable craftsmanship, and unparalleled charm, 116 Stromboli Drive presents an extraordinary opportunity to embrace the quintessential Florida lifestyle. Whether seeking a permanent residence, a vacation getaway, or an investment opportunity, this coastal retreat offers a rare combination of luxury, comfort, and convenience. Welcome home to 116 Stromboli Drive—where every day feels like a vacation, and paradise awaits at your doorstep.

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$2025.9

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Private Vacation Home

Oceanfront Luxury Residence, Infinity Pool, Rooftop Sunset Terrace, 29 Night Min

Islamorada, Florida, United States

Aurora Sands is an exclusive oceanfront estate in Islamorada brought to you by Your Keys Vacations that is designed for elevated coastal living and extended luxury stays. Overlooking the Atlantic, this modern retreat blends refined design with seamless indoor-outdoor spaces, offering privacy, comfort, and effortless entertaining in the heart of the Florida Keys.brbrThe home features expansive living areas filled with natural light, curated coastal interiors, and panoramic water views throughout. Designed for gathering, Aurora Sands includes two full chef’s kitchens — one indoors and one outdoors — both equipped for large groups with generous seating, multiple cooking and grilling options, ice makers, beverage coolers, and ample prep space.brbrOutside, guests enjoy a private resort-style setting with an infinity-edge pool & jacuzzi, spacious lounge areas, and a rooftop terrace ideal for sunset cocktails or morning coffee overlooking the ocean. The layout was thoughtfully designed for both relaxation and connection, making it perfect for extended family stays, seasonal escapes, or executive retreats.brbrSpacious bedrooms, spa-inspired bathrooms, and high-end finishes throughout create a serene atmosphere that feels both luxurious and welcoming. Enjoy your own private beach while still in close proximity to Islamorada’s best marinas, dining, and excursions, Aurora Sands offers the rare balance of tranquility and convenience.brbrAvailable for extended stays, Your Keys Vacations presents Aurora Sands in Islamorada. New to the luxury rental market, Aurora Sands delivers the privacy of a private estate with the experience of a boutique waterfront resort.

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Exceptional(1)

$580.65

/ Nightly

Private Vacation Home

Canalfront home in Safety Harbour in Islamorada, with 4 bedrooms and a pool.

Islamorada, Florida, United States

Safety Harbour Canalfront - Safety Harbour Canalfront Home. Fabulous, protected dockage right outside your home! This canal front home consists of three bedrooms and two bathrooms upstairs along with an open concept living room, dining room and kitchen with the 4th bedroom and bath located on the ground level with its own private entrance. Beautiful canal side heated swimming pool and 100 feet of protected dockage. Easy access to the bay and the ocean under Channel 5 Bridge. brbrIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

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Exceptional(1)

$2808.64

/ Nightly

Private Vacation Home

Islamorada Beach Beachfront, Fire Pit & Pool

Islamorada, Florida, United States

Welcome to Wander Islamorada Beach, a luxurious three-story, six-bedroom beachfront property. Enjoy three living rooms, a social room, a beachfront terrace, a third-story oceanfront terrace, and a private pool. Nestled in a beautiful cove with a rare natural beach, this elegant home includes two paddle boards and two kayaks for your enjoyment.brbrSECURITYbrFor security, there is a ring camera on the exterior of the front door at this Wander. There are no other cameras inside your Wander home.

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Exceptional(1)

$770.63

/ Nightly

Private Vacation Home

New Listing! Spacious 5/5.5, Pool, Waterfront Home in Islamorada, Private Beach

Islamorada, Florida, United States

New Construction Residence in the Sunny Florida Keys luxury community of Port Antigua, Islamorada, w/ private crystalline beach & bayside entertainment facilities. This residence boasts an incredible floorplan w/ dedicated entertaining areas on the 1st floor: 2 full baths, 1 bedroom, patio w/ AC reel room. Saltwater pool w/ jets overlooks a 50' reinforced concrete dock & seawall along a canal w/ ocean access. The 2nd floor features 3 bedrooms, 2.5 bathrooms, modern European gourmet kitchen w/ superior stainless steel JennAir appliances, Calacata Quartz counters, island, & spacious living room w/ wet bar. 3rd floor private master suite features sumptuous bath, vaulted ceilings, & balcony w/ sweeping views.brDetails:brMaster Bedroom - King Size BedbrBedroom 1, 2, 3, 4 - Queen Size BedsbrWasher/DryerbrBarbecuebrCabana Bath

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Most popular vacation rentals in Islamorada

Exceptional(1)

$1588.39

/ Nightly

Cottage

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Islamorada, Florida, United States

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Exceptional(1)

$1719.90

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Private vacation home

Private Beach / Private overwater dock / Heated Pool / Mahi Key

Islamorada, Florida, United States

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Exceptional(1)

$1716.73

/ Nightly

Private vacation home

Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina

Islamorada, Florida, United States

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Exceptional(1)

$1606.37

/ Nightly

Private vacation home

Oceanfront Keys Escape | Private Beach & Pool | 3 Acres

Islamorada, Florida, United States

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Exceptional(1)

$1600.73

/ Nightly

Private vacation home

Discover Sea Ranch in Islamorada: spacious 4BR home with private pool and stunning views.

Islamorada, Florida, United States

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Exceptional(1)

$1595.07

/ Nightly

Private vacation home

Experience luxury at Little Bay Compound in Islamorada with stunning views.

Islamorada, Florida, United States

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Exceptional(1)

$1510.57

/ Nightly

Private vacation home

Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!

Islamorada, Florida, United States

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Exceptional(1)

$1409.53

/ Nightly

Private vacation home

Experience luxury at The Sapodilla House, a stunning 5-bedroom waterfront retreat in Islamorada.

Islamorada, Florida, United States

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Exceptional(1)

$1433.51

/ Nightly

Condo

Experience luxury at Coastal Cove Villa, a 4-bedroom retreat in beautiful Islamorada!

Islamorada, Florida, United States

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Exceptional(1)

$1948.66

/ Nightly

Private vacation home

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

Islamorada, Florida, United States

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Vacation Home Rentals By Owner In Islamorada, FL

$431.9

$2025.9

$580.65

$2808.64

$770.63

Rent a place that suits your needs

Most popular vacation rentals in Islamorada

$1588.39

$1719.90

$1716.73

$1606.37

$1600.73

$1595.07

$1510.57

$1409.53

$1433.51

$1948.66

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