Vacation Home Rentals By Owner In Islamorada, FL

Showing 120 Of 365 Vacation Rentals

$1008.06

Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside

Islamorada, Florida, United States

Poolside,3 Queen Beds,1 Pull OutbrbrWelcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. Every detail and fixture was handpicked and custom crafted from the finest materials and builders.brbrInspired by the Caribbean lifestyle and design from Ocean Gardens Showroom. The Jamaican Palm is an expansive 3 bedroom, two-bathroom single home with a large great room, chefs kitchen and outdoor wrap-around veranda. Chisel stone flooring, granite countertops, Keys Stone Coral wall and custom cabinets are just a few of the high quality features the home holds. The chefs commercial kitchen features a Wolf stove, Subzero refrigeration and a separate built-in wine cooler.brbrNautical decor includes one of a kind Marine Antiques and ship lighting throughout the home. Like all our other homes, The Jamaican Palm also comes with a washer-dryer, Weber BBQ gas grill, wireless Internet and cable TV.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

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Sleeps

Exceptional(3)

$1716.73

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

King, Queen2 twins, 1 pullout. Boat DockagebrbrCustom designed and built from the ground up by resort owner Phil Sena brwith nothing compromised this luxurious Caribbean home is on the oceansbredge with 180 degrees of unobstructed ocean views and sunrises. Withbrcomplete privacy, this site is home to famous movie shoots, celebritybrweddings and family reunions.brbrCaribbean homes with 450-foot fishing pier and beach entry pool keep guestbrcoming back. Its the off-shore fishing and diving that makes it so hard tobrleave. Located on a deep-water channel with protected dockage

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Sleeps

$1792.11

/ Nightly

Private Vacation Home

Royal Palm North 3 Bedrooms, 3 Baths, Ocean Front,

Islamorada, Florida, United States

King, Queen2 twins, 1 pullout. Boat DockagebrbrCustom designed and built from the ground up by resort owner Phil Sena with nothing compromised this luxurious Caribbean home is on the oceans edge with 180 degrees of unobstructed ocean views and sunrises. With complete privacy, this site is home to famous movie shoots, celebrity weddings and family reunions.brbrCaribbean homes with 450-foot fishing pier and beach entry pool keep guestbrcoming back. Its the off-shore fishing and diving that makes it so hard tobrleave. Located on a deep-water channel with protected dockage

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Sleeps

$309.38

/ Nightly

Private Vacation Home

Gorgeous Newly Renovated 2-bedroom Townhome in Islamorada w/Pool and Boat Slip

Islamorada, Florida, United States

Experience Islamorada like a local in this perfect 2-bedroom townhome. The master bedroom features a king bed, while the second bedroom offers a cozy queen bed. Guests can relax in the delightful living room. With two bathrooms, each equipped with a refreshing shower, getting ready is a breeze. Gas BBQ, TV and WiFi. Carport For Two Cars, Pool, Tiki Hut, Boat slip and Boat rental available nearby. Also Washer Dryer in unit. Storage shed with Bike path at our door. Security front gate The serene atmosphere invites you to unwind after a day of adventure. We think our place will help you experience everything Islamorada has to offer.

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Exceptional(1)

$1370.95

/ Nightly

Private Vacation Home

Coastal Retreat in the Heart of Islamorada

Islamorada, Florida, United States

Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experience for those looking for a luxurious and private getaway. Each spacious bedroom and en suite bathroom is inspired by modern coastal furnishings. Perfect for entertaining family and friends, including a fully equipped kitchen and an outdoor grilling area. Plus, enjoy the privacy of your own pool and patio that extend from the living area. brLocated in the very heart of Islamorada, where you can explore its vibrant culinary scene with some of the best restaurants, breweries and live music in town. Choose from Square Grouper, Pierre's and Morada Bay to Green Turtle Inn, Florida Keys Brewery or Islamorada Beer Company. To experience more of what Islamorada has to offer, take part in various activities, such as visiting the Theater of the Sea or Founders Park, kayaking or paddle boarding, or even chartering a boat for deep sea fishing or diving at one of many marinas around town. brGolf cart rental available at daily or weekly rates.

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Exceptional(28)

$387.0

/ Nightly

Private Vacation Home

Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada

Islamorada, Florida, United States

Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing getaway, look no further. Relax with the family in this cozy Island retreat. Completely remodeled! Come enjoy the community heated pool and a morning bike run. Enjoy the Florida Keys with your own private backyard and private parking.

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Exceptional(1)

$287.07

/ Nightly

Private Vacation Home

Executive Bay Club Bayfront/Beachfront paradise

Islamorada, Florida, United States

Watch the sunset from your private balcony from this bay front , beach front townhouse/condo. Recently remodeled and fully furnished for tour enjoyment. Located in the heart of Islamorada, right next to lovely Founder’s Park.

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$525.26

/ Nightly

Private Vacation Home

Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream

Islamorada, Florida, United States

Welcome to Paradise! This fabulous Keys home with Tommy Bahama décor throughout is a Fisherman & Water Enthusiast's Dream! ***Ask about reduced seasonal rates Sept thru Nov! Located in a beautiful, quiet cul-de-sac, on a deep water canal with access to the community's private beach & private boat ramp is minutes by boat to the Florida Bay and Atlantic Ocean. This Non-Smoking, 3 Level home has amazing views and world-class sunsets. 3 Bedroom with 2 additional sleep areas and 3.5 Bathrooms sleeps 10 with the possibility of easily accommodating more. Gourmet kitchen has a commercial Viking gas stove & SubZero refrigerator. If you're looking for a home that will make everyone happy, this is it! For the fisherman, the 100 ft. seawall is perfect for fishing from or docking your boat with cleaning station, electric & water. (Boat lift available on-site for additional rate for up to 26ft vessel.) Underwater canal lights offer lots of entertainment after dark as you may see sharks, tarpon, turtles, manatee and tons of fish. For the Beach Bum, the keycard allows entrance into the community's Private Beach only minutes away, where Tiki Huts and Grills are available to spend a fantastic day and watch the amazing sunsets. Water Sports anyone With house rental and liability release we offer 3 Kayaks & 5 Stand Up Paddle Boards with Paddles & Life Jackets for hours of exploring the ocean & inter-coastal waterways. Or paddle over to the Private beach to meet up with the rest of the group. This home's location is close to fabulous dining, shopping and entertainment which we are happy to make recommendations. Interested in chartering a private fishing, scuba diving or sightseeing trip, just let us know and we can make it happen. Housekeeper is available weekly for an additional charge weekly.

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$2467.09

/ Nightly

Private Vacation Home

Oceanview 4BR Villa + Resort Perks | Bunks | Sleeps 10

Islamorada, Florida, United States

Built for the way families actually vacation, this villa at The Islands of Islamorada, a private, gated oceanfront resort in the Florida Keys, offers over 3,100 square feet of thoughtfully designed space to spread out without sacrificing comfort or style.brbrThree en-suite king bedrooms serve the adults, while a dedicated bunk room gives the kids a space to call their own. A full kitchen, dining room, and ground-floor loggia create the relaxed, at-home atmosphere that turns a stay into something more. Private balconies, a laundry room, and a two-car garage complete the picture, with select villas also featuring private elevator access.brbrBeyond the villa, enjoy access to a full suite of resort-style amenities. Spend your days between two swimming pools and a jacuzzi, unwind at the oceanfront bar or around the fire pits, or take advantage of paddleboards, kayaks, and Hobie Cat sailing, all just steps from your villa. Guests also have access to a fitness center, yoga classes, pickleball courts, a playground, and grill stations, along with 24-hour on-site assistance and property-wide high-speed internet.

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$2496.35

/ Nightly

Private Vacation Home

Oceanfront + Resort Perks | 4BR Villa (Sleeps 8)

Islamorada, Florida, United States

This oceanfront villa at The Islands of Islamorada, a private, gated oceanfront resort in the Florida Keys, represents the pinnacle of the experience, oriented directly toward the Atlantic with unobstructed ocean views from every level.brbrSpanning three stories and over 3,100 square feet, the home offers three en-suite king bedrooms and a private twin room, creating an elegant, unhurried setting for up to eight guests. A full kitchen, dining room, and ground-floor loggia invite the kind of easy, indoor-outdoor living the Florida Keys does best. Private balconies, a laundry room, and a two-car garage complete the experience, with select villas also featuring private elevator access.brbrBeyond the villa, enjoy access to a full suite of resort-style amenities designed for both relaxation and activity. Spend your days between two swimming pools and a jacuzzi, unwind at the oceanfront bar or around the fire pits, or take advantage of paddleboards, kayaks, and Hobie Cat sailing, all just steps from your villa. Guests also have access to a fitness center, yoga classes, pickleball courts, a playground, and grill stations, along with 24-hour on-site assistance and property-wide high-speed internet.

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$2219.64

/ Nightly

Private Vacation Home

4BR Oceanview Villa | Accessible + Resort Perks

Islamorada, Florida, United States

Spacious, thoughtfully designed, and fully accessible, this three-story villa is part of The Islands of Islamorada, a private, gated oceanfront resort in the Florida Keys. Offering over 3,100 square feet of open living space, the home features ADA-compliant design, private elevator access to every level, and welcomes dogs for a seamless stay.brbrThree en-suite king bedrooms and a twin room comfortably accommodate up to eight guests, while a full kitchen, dining room, and ground-floor loggia create the relaxed, at-home rhythm that defines a stay in Islamorada. Private balconies, a laundry room, and a two-car garage complete the experience.brbrBeyond the villa, enjoy access to a full suite of resort-style amenities designed for both relaxation and activity. Spend your days between two swimming pools and a jacuzzi, unwind at the oceanfront bar or around the fire pits, or take advantage of paddleboards, kayaks, and Hobie Cat sailing, all just steps from your villa. Guests also have access to a fitness center, yoga classes, pickleball courts, a playground, and grill stations, along with 24-hour on-site assistance and property-wide high-speed internet.

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$2205.0

/ Nightly

Private Vacation Home

Oceanview Living + Resort Perks | 4BR Villa

Islamorada, Florida, United States

Enjoy abundant space with spectacular Atlantic Ocean views at The Islands of Islamorada, a private, gated oceanfront resort in the Florida Keys. Designed for seamless indoor-outdoor living, this villa offers over 3,100 square feet of thoughtfully appointed space, creating a relaxed and elevated setting for your stay.brbrThree en-suite king bedrooms and a twin room comfortably accommodate up to eight guests, complemented by a full kitchen, dining room, laundry room, ocean view balconies, and a two-car garage. Select villas also feature private elevator access to every level.brbrBeyond the villa, enjoy access to a full suite of resort-style amenities. Spend your days between two swimming pools and a jacuzzi, unwind at the oceanfront bar or around the fire pits, or take advantage of paddleboards, kayaks, and Hobie Cat sailing, all just steps from your villa. Guests also have access to a fitness center, yoga classes, pickleball courts, a playground, and grill stations, along with 24-hour on-site assistance and property-wide high-speed internet.

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Sleeps

Exceptional(77)

$2449.39

/ Nightly

Private Vacation Home

Private Beachfront Estate with Resort-Style Pool & Pier

Islamorada, Florida, United States

Welcome to a private beachfront estate on the ocean side in Islamorada where refined comfort meets the ease of a luxury resort. With 5 bedrooms and 6.5 bathrooms, this spectacular property is exceptionally well suited for couples traveling together, family celebrations, and multigenerational getaways. Set across beautifully designed resort-style grounds, the home offers an elevated vacation experience with standout amenities including a private fishing pier, pickleball, mini golf, basketball Pop a Shot, ping pong, kayaks, bikes and so much more. From sun-soaked days by the pool to peaceful mornings on the water and effortless evenings gathered with family and friends, every detail is designed to deliver the space, privacy, and lifestyle that make a Florida Keys stay truly unforgettable.

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Exceptional(4)

$889.95

/ Nightly

Private Vacation Home

Ultimate luxury vacation home in Islamorada, Florida!

Islamorada, Florida, United States

SPECTACULAR HOME AND FISHERMAN'S PARADISE IN VENETIAN SHORES! This home is located in close proximity to many shopping and dining options and is 1 mile south of Founder's Park which offers many amenities such as a beautiful beach, play ground, pool and marina to name a few. The property features a 70' concrete dock on deep water canal which opens directly to Snake Creek for quick and easy access to bay or ocean; beautifully furnished 5 bedrooms/4.5 baths; private master retreat with gorgeous bath on third level; marble floors throughout; elevator; FABULOUS chef's kitchen with Wolf gas range and huge island; large terraces and fantastic entertaining spaces; Sonos wireless sound system throughout; outdoor kitchen on ground level next to beautiful pool. A true paradise.

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Exceptional(2)

$500.63

/ Nightly

Private Vacation Home

Welcome to Our Beautiful Spacious 2 BR Home in the Heart of Islamorada, Florida

Islamorada, Florida, United States

Experience the perfect getaway in our stunning 2-bedroom home located in the vibrant heart of Islamorada, Florida. Nestled amidst lush tropical surroundings, this beautiful property offers the ultimate blend of comfort, luxury, and adventure. Whether you’re looking to relax by the pool, explore the nearby waters, or enjoy the local dining and shopping, our home provides the ideal base for your vacation.brbrIf you're a boater- this is your spot. Centrally located and close to all the amenities in Islamorada from the spectacular lighthouse and sandbars which is only minutes away to all the best restaurants!brbrPLEASE NOTE: we are only allowed per the city of Islamorada for 28 days rentals. Please contact with any questions prior to booking.

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$1457.14

/ Nightly

Private Vacation Home

Gorgeous bayfront Snappy Turtle: Spacious 4BR home in Islamorada with open water views!

Islamorada, Florida, United States

Escape to paradise at this stunning bayfront home in Lower Matecumbe, Islamorada. With breathtaking open bay views, a private heated pool, and plenty of space to unwind, this 4-bedroom, 3.5-bath retreat is perfect for your next Keys getaway.brbrStep inside to an inviting main level featuring a spacious living area, fully equipped kitchen, and dining room—all designed for gathering and making memories. A convenient half bath is also located on this floor.brbrUpstairs, you'll find three comfortable bedrooms and two full bathrooms, offering the perfect blend of privacy and convenience. But the true highlight awaits on the top floor—your own private sanctuary. The master suite boasts a luxurious bedroom, an en-suite bathroom, and a dedicated living room with spectacular water views.brbrOutside, soak up the Florida sun by the heated pool, sip cocktails as you watch the sunset over the bay, or launch your water adventures right from your backyard. Whether you're fishing, boating, or simply relaxing, this Islamorada gem is the ultimate Keys escape.brbrBook your stay today and experience the magic of bayfront living!

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Sleeps

Exceptional(7)

$566.57

/ Nightly

Private Vacation Home

Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.

Islamorada, Florida, United States

Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and private dock, close to the best restaurants, and sight seeing. Peaceful, quiet and relaxing! Just what is needed to take your mind off of business and a great place to spend the winter months in turquoise, warm waters. Fish, read a book, swim, head to Key West, shop, eat, drink, enjoy the Florida Keys.

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Sleeps

Exceptional(3)

$631.3

/ Nightly

Private Vacation Home

Enjoy a serene stay at Peaceful Palms 3 in Islamorada with ocean views.

Islamorada, Florida, United States

Welcome to Peaceful Palms, a 3-bedroom, 3-bathroom townhome that's all about easy, laid-back island living. Tucked away in Islamorada, this spot has everything you need for the perfect getaway—boho coastal vibes, plenty of space to relax, and access to a gorgeous community pool.brbrInside, you'll find bright, open spaces with natural textures and beachy tones that feel like a breath of fresh air. Each bedroom is its own little retreat, and with three bathrooms, no one's waiting in line after a day out in the sun.brbrSpeaking of the sun, the community pool is just steps away, ready for lazy afternoons with a good book or a quick dip to cool off. And when you're ready to explore, you're in the heart of Islamorada—close to amazing restaurants, fun waterfront spots, and some of the best fishing in the world.brbrWhether it's sipping your morning coffee on the balcony or catching the sunset after a full day of adventures, Peaceful Palms is where the best kind of memories are made. Come see for yourself—you won't want to leave!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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Sleeps

Exceptional(2)

$404.42

/ Nightly

Private Vacation Home

Boater's Paradise

Islamorada, Florida, United States

brThis incredible property in Islamorada is the ultimate getaway, offering a spacious and flexible layout with 9 beds—perfect for family reunions, large groups, or anyone seeking a luxurious Florida Keys escape. With 2,000 sq ft of living space under air, plus an additional secured lot for RVs, jet skis, boats, and recreational vehicles, this home is tailored to outdoor enthusiasts and boaters alike.brbrA true boater’s paradise, the property boasts 100' of dockage, a private boat slip, and convenient free on-site boat trailer parking on the adjacent lot. The approximately 5 ft deep canal is perfect for maneuvering a 46.6 ft Bertram, with plenty of room to comfortably turn around, and the open Atlantic Ocean is just 1/8 mile away for easy access to world-class fishing and watersports.brbrInside, the home features a fully stocked kitchen with an additional refrigerator in the laundry room next to the washer and dryer. A bait freezer is also conveniently located on the side patio adjacent to the dock. The flexible sleeping arrangements allow for single beds to be converted to Continental Kings, ensuring comfort for all guests. This Smart Technology home offers multiple areas for socializing, recreation, and relaxation, including three separate patio spaces equipped with shade sails and Edison lights, perfect for enjoying the warm Florida evenings.brbrWhether you’re here for adventure or relaxation, this one-of-a-kind property is designed to offer the best of both worlds, making it the perfect place for an unforgettable stay in the Florida Keys.

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$523.63

/ Nightly

Private Vacation Home

Discover One Too Mini, a cozy 3-bedroom getaway in Islamorada, perfect for 8!

Islamorada, Florida, United States

This charming 3 bedroom ground-level home is located in the private gated community of Bay Hammock on Upper Matecumbe in Islamorada. Enjoy a heated pool, a comfortable island setting, and the relaxed lifestyle the Florida Keys are known for.brbrBoaters welcome — inquire within about bringing your boat! The community boat basin offers a boat slip available for use, making it easy to get out on the water and enjoy some of the best fishing and boating the Keys have to offer. Perfect for a laid-back getaway in a quiet, private neighborhood.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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Bath

Sleeps

Rent a place that suits your needs

Condo

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Hotel resort

View 23 Hotel resort

Private vacation home

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Villa

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Most popular vacation rentals in Islamorada

$1588.39

/ Nightly

Cottage

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Islamorada, Florida, United States

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$1719.90

/ Nightly

Private vacation home

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

Islamorada, Florida, United States

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$1716.73

/ Nightly

Private vacation home

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

Islamorada, Florida, United States

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$1606.37

/ Nightly

Private vacation home

Oceanfront Keys Escape | Private Beach & Pool | 3 Acres

Islamorada, Florida, United States

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$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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$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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$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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$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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Sleeps

$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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Bath

Sleeps

$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

$1008.06

$1716.73

$1792.11

$309.38

$1370.95

$387.0

$287.07

$525.26

$2467.09

$2496.35

$2219.64

$2205.0

$2449.39

$889.95

$500.63

$1457.14

$566.57

$631.3

$404.42

$523.63

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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