Vacation Home Rentals By Owner In Islamorada, FL

A perfect Keys home located in the heart of Islamorada in the sought-after Port Antigua community with access to the homeowner's private beach. This updated home is spacious with 2 bedrooms and 2 bathrooms. There is a huge balcony with a sitting area, dining table, and BBQ where you can enjoy your morning coffee or after-dinner drink with a view of the canal. Port Antigua is a quiet and friendly neighborhood that will ensure your peaceful stay. Fish off the dock, bask in the sun, and enjoy the private pool or bring your small boat (no lift). There is a community ramp where you can launch your boat and enjoy the incredible water of the Florida Keys. Bike riding is also available along the Port Antigua streets. Enjoy the beautiful sunsets on the beach while you sip your favorite drink, or walk along the sandy beach as you enjoy the tranquil moments at the Florida Keys. You can also enjoy excellent restaurants minutes away or visit Dolphin Research Center or Island Dolphin Care to experience the beauty of dolphins. In addition, Key West is only a short drive where you can spend a day exploring. Whether you choose to relax or adventure, our home will be a perfect fit.brbr*Long term rental welcomed br*No pets allowedbr*Non smoking homebr

Beautiful vacation home in the heart of Islamorada , Florida Keys

Islamorada, Florida, United States

Bed

Bath

Sleeps

$204.64

Vacation like a local! This charming 2 bedroom, 2 bath home is located in one of Islamorada’s quaintest and quietest neighborhoods of just 40 residences.brbrThis home is bright and tropically decorated. The master suite features a private bath with shower. The second bedroom shares the hall bath with the main living area. brbrThe backyard has a large Tiki Hut to sit and enjoy the beautiful weather and an outdoor fenced in shower to rinse off after a day on the water or a bike ride. brbrThere is a large closed in air-conditioned porch right off the kitchen where you can enjoy your morning coffee as you start your day or sit and unwind at the end of each day. From the porch, you can see the private park exclusively for the neighborhood.brbrClose to restaurants, charter boats and outdoor activities. brbrThis home is the perfect spot for a Florida Keys retreat.

Off the beaten path in one of Islamorada’s hidden gem of a community!.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$762.55

Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards and more. The main living area is located on the upper level of this oceanfront cottage and has open ocean views throughout. The open concept kitchen, living and dining room are great for entertaining. The main level has two bedrooms and two baths. The lower level is a separate living area with 2 sets of bunk beds, a living room, kitchenette and bathroom. It can be added when renting the upstairs for an additional $600 weekly. The Leatherback Cottage can be rented separately or in combination with any of the four other homes.brVACATION RENTAL LICENSE: 24-0386brIf booking more than a year in advance current prices may not reflect the 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.

Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1600.73

Sea Ranch - Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in the beachside pool. The front home sits waterfront with two bedrooms and two bathrooms. The cottage sits back on the property with two bedrooms and one bathroom. Entertain in the pool room with pool table, wet bar, poker table and more. brThe ocean front paradise is also a 'Destination/Wedding Location!' $8,000/week & $24,000.00/month. brbrThe viewing dock is just that, it is too shallow for boats, so boats are prohibited. 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.

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

Islamorada, Florida, United States

Bed

Bath

Sleeps

$517.69

Islamorada is considered the fishing capitol of the world!You can do deep sea,offshore game and back country fishing!Its bountiful reefs contain a wide variety of sea life ready to explore on your next scuba or snorkeling adventure. There are numerous diving and fishing charter boats ready to take you to the action!Visit the The Theatre of the Sea MM84.5 for a fun and informative way to learn about our under sea life,they also offer tours that let you swim with dolphins, sea lions and rays!Visit The History of Diving Museum MM83, which tells the international story of mankind’s attempts to explore, understand and venture under the sea.Take a tour on the Historical Lignumvitae Key Botanical State Park MM78.5 accessible by private boat, kayak, canoe or tour boat for a day of nature exploration and visit the Matheson House, built in 1919 to get of glimpse of early key living.Stop by Robbie's or Bud and Mary's marina and feed the giant Tarpons in the wild!You are sure to have a great timebrbrbrTrailer Storage: Trailer storage is available from Bayside Storage 2 minutes away for a small fee, ask manager for details. However you may choose to store your trailer with anyone of your choosing. Trailers may not be parked on house property. The nearest ramp is located at Founders Park about 1 mile away.brbrBeach: The nearest beach is located at Founders Park about 1 mile away. For our boater guests the 'sand bar' is located in front of Holiday Isle ocean side about 8-10 minute boat ride south of the property. MINIMUM 28 DAY STAY

Islamorada's Finest Canal Front 'One Story' Vacation Home WiFi-HDTV-NO STAIRS

ISLAMORADA, Florida, United States

Bed

Bath

Sleeps

$381.41

Hawksbill Cottage - The Hawksbill Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the oceanfront property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards, oceanfront shaded tiki area and more. This peaceful garden bungalow is secluded in lush tropical landscaping. It features a king bedroom, bathroom with walk-in shower, kitchen, living room and private patio. The decor and furnishings give it a tranquil feel. The Hawksbill Cottage can be rented separately or in combination with any of the other four homes. There is a cottage above the attached garage, referred to as The Treehouse, that is convenient to rent for family and friends.brVACATION RENTAL LICENSE: 24-0416 brIf booking more than a year in advance current prices may not reflect the 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. brPlease 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.

Cozy 1-bedroom Hawksbill Cottage in Islamorada, perfect for a romantic getaway.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$208.96

Escape to Your Florida Keys Getaway – A Slice of Paradise in IslamoradabrWelcome to our beautiful 2-bedroom, 2-bathroom townhome in the heart of the Florida Keys. Whether you're looking for adventure or relaxation, our home offers the perfect balance of both.brbrAmenities & Outdoor FunbrRelax & Unwind – Lounge by the large, heated pool, soak up the sun swimby the dock or take in breathtaking sunsets from the fishing pier/dock.brbrExplore with Ease – Enjoy our two beach cruiser bikes, Kayak from our beach in our 2 single person kayaks brbrStay Active – Play on the pickleball and tennis courts or head next door to Founders Park, which features baseball and soccer fields, a beach volleyball court, a marina, and an Olympic-sized swimming pool.brbrModern Comforts – Stay connected with free Wi-Fi throughout the home and clubhouse. Smart TV's to enjoy streamingbrbrEntertainment for All – Enjoy streaming your favorite shows on smart TVs in the living room and primary bedroom. Plus, we provide board games for memorable family game nights.brbrPrime Location – Islamorada brOur townhome is nestled in Islamorada, known as the Sport Fishing Capital of the World and home to incredible wildlife. Located in a private, gated community with 24/7 security, you’ll be minutes from world-class fishing, diving, and snorkeling.brbrYour Home Away from HomebrSpacious & Comfortable –brbrUpstairs: Two bedrooms accessed via a spiral staircase. The primary bedroom features a king-size bed and a queen sleeper sofa with a Tempur-Pedic mattress. The guest bedroom has a queen-size bed.brbrDownstairs: Open-concept dining and living area with a new queen-size sleeper sofa (also with a Tempur-Pedic mattress).brbrWork-from-Paradise Setup: The primary bedroom has a dedicated workspace with a monitor, keyboard, and mouse, plus strong, reliable Wi-Fi for remote work.brbrFully Equipped Kitchen & Outdoor Dining – Cook a delicious meal in the fully stocked kitchen or fire up the BBQ grill on the back patio. Enjoy your meal at the outdoor dining table with an umbrella, perfect for morning coffee or sunset cocktails.brbrAll the Essentials Provided –brbrLinens, towels, and beach towelsbrbrHairdryers and complimentary starter toiletries (shampoo, conditioner, bath gel, lotion, and hand soap)brbrIn-unit washer & dryer for added conveniencebrbrExtra Perks & Nearby ShoppingbrPublix & Winn Dixie supermarkets are just 4 miles awaybrbrWest Marine & Bass Pro Shops for all your outdoor needsbrbrQuaint local shops and waterfront restaurants to explorebrbrImportant NotesbrDock Use: Our fishing dock is not available for guest boat docking, but it’s a fantastic place to watch for manatees and swap fish tales with fellow guests.brbrAccessibility Notice: Please note that this unit is not disability-friendly. It features a spiral staircase leading to the bedrooms, which may not be suitable for guests with mobility challenges. If you have any concerns about accessibility, please feel free to reach out before booking.brbr brCome experience the best of the Florida Keys—whether it’s adventure-filled days or tranquil nights, this is your perfect getaway.brbrBook your stay today and start making unforgettable memories.

Keys Getaway – 2 Bikes, Heated Pool, Small Beach & Sunset Dock Views

Islamorada, Florida, United States

Bed

Bath

Sleeps

$191.95

This two-story house is located on an ocean access canal that is literally minutes from the Atlantic Ocean. Guest can dock their boat (max. length of 32') in the backyard and be on the Ocean in just a few minutes. The front of the house faces the Atlantic Ocean with views of the ocean. The home is updated and has an open layout with volume ceilings. The master bedroom has a queen size bed with attached master bathroom. The second bedroom has bunk beds with a trundle, which sleeps 5 people. The great room has a love seat, and a sleeper sofa, which sleeps 2 adults. Guests can enjoy views of the ocean from the balcony. There is covered parking for 2 cars.

Beautiful water front home, private dock in Islamorada, World Fishing Capital

Islamorada, Florida, United States

Bed

Bath

Sleeps

$2706.47

Summary:brbrThis is a truly unique and spectacular Villa thanks to its breathtaking view of the sea and its warm sandy beach.brbrbrbrOn the stunning beach you will find paddle boards and kayaks (both for rent) and comfortable sun loungers while you sunbathe and enjoy the dreamy sunsets.brbrbrbrGet ready for a private saltwater pool with lush tropical landscaping plus a cozy cabana with a dining table, a cinema (projector) and a lovely fire pit!brbrbrbrThe interior has 4 bedrooms, 4 bathrooms and much more!brbrbrbrLicense # 24-4115brbrbrbrThe Space:brbrBEDROOMSbrbrbrbr1. Master Bedroom with a KING SIZE BED with excellent quality linens. A balcony with an amazing view of the beach and access to a full private bathroom with a hot tub.brbr2. Bedroom with a QUEEN SIZE BED and access to a full private bathroom.brbr3. Bedroom with THREE QUEEN SIZE BEDS and access to a full private bathroom.brbr4. Bedroom with TWO FULL SIZE BEDS and access to a full private bathroom.brbrbrbr*Two extra air mattresses.brbrbrbrAll the bathrooms are stocked with the toiletries our guests will need; towels are also included.brbrbrbrPerfect for large groups.brbrbrbrThe Villa has a cherry hardwood flooring throughout, Also, a fully equipped kitchen with granite/stainless appliances and a gas stove.brbrbrbrTHE VILLA HAS AN OUTDOOR CAMERA TO CONTROL WHO GOES IN AND OUT, ALWAYS LOOKING FOR OUR GUEST SAFETY.brbrbrbr-kayaks and paddle boards are available for rent only we don’t provide them, we have a partnership with a Keys rental for this!brbrbrbrOther Things to Note:brbr- This property is pet friendly.brbr$300 per petbrbr-brbr- If you want the pool to be heated, request it 48 hours prior arrival.brbrbrbr- BUGS & CRITTERS: Please note we routinely spray the property for bugs and insects, however if you do come across any little critters please keep in mind that Florida is a sub-tropical climate. To help prevent this, keep the doors closed.brbrbrbr-Propane tanks for the fire pit and grill will need to be replaced by guests at the moment they use it, if guests found it empty we will refund the refill of the tank, but guests need to take care of propane.brbrbrbr-Unfortunately we are experiencing a strange amount of seaweed at the shore by this time of the year, this is affecting all florida area!

Ocean Villa | BeachFront Paradise by Glam Homes

Islamorada, Florida, United States

Bed

Bath

Sleeps

$442.63

Bayside Retreat - Completely renovated bayfront duplex home. This bayfront home consists of three bedrooms and three baths in Lower Matecumbe. With charming island decor and the open concept living room, kitchen and dining area, the home is light and airy. The screened balcony directly off the kitchen enables you to enjoy outdoor dining with beautiful bay views. The master en-suite with a king bed and bay views, and the guest room with two twin beds are located on the main level. The loft queen en-suite on the second level with sliding doors leading out to an open balcony offers open Gulf views to the west and ocean views on the east. This home offers both ocean views and bay views from the kitchen and living room. Dockage for smaller boats and skiffs up to 24' with easy bay access and ocean access through Channel 5 Bridge. Enjoy paddle boarding and kayaking right from the bayfront beach area. There are 2 paddle boards for your enjoyment at the property. Enjoy the refreshing bayside pool.brIf booking more than a year in advance current prices may not reflect the 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. brPlease 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.

Bayside Retreat: Enjoy stunning open water views in this 3-bedroom home in Islamorada.

Islamorada, Florida, United States

3

Bed

3

Bath

6

Sleeps

$272.14

This Islamorada house boasts 2 inviting bedrooms with 1 full bed and 1 king bed. The serene atmosphere and lovely decor make it a phenomenal retreat for guests. With amenities like a washing machine, hair dryer, WiFi, and AC, you'll feel right at home. The 2 bathrooms offer additional comforts like a bidet. Plus, there's an extra living space with a sofa bed for added convenience. It's easy to see why you'll be able to unwind at our place. While your experience will be private, you will have full access to all of the Sun Outdoors' resort amenities and activities. Including, 2 heated pool, clubhouse, game lawn, billiards, and much more! A social calendar for all guests is always available for those that wish to be more social!brA min of 28 nights is required for these homes.

Lovely 2-bedroom house in ocean front resort.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1148.36

Remarkable home nestled in the heart of Islamorada where you will find large outdoor spaces with outdoor dining and private lounge areas with private salt water pool and outdoor kitchen. Spacious interior with large open kitchen including convection oven, wine fridge and large island with seating area, living room with comfortable large sofa, smart TV and separate dining. Occupies 8. One Spacious bedroom with on suite and large shower downstairs and three upstairs. Master Bedroom upstairs boasts a large master bath spectacularly designed with large wet bath featuring a shower and floating bathtub for soaking in a spa like setting. Sleep in luxury with comfy linens and blackout curtains in all bedrooms all with smart TV’s, king size beds on 3 of them and 1 with 2 full size beds. Extensive upstairs terrace with access from the master bedroom and guest bedroom includes a sitting area to take in the wonderful night breezes and extraordinary sunset views. Quiet street and private beach next to the luxurious Cheeca Lodge. Walk to many restaurants and shops, close to water activities, marinas, Founders park, and wonderful cafes and shops. Supermarket nearby, golf cart rentals, bike rentals and kayaks. Show your reservation for free entry to Founders Park offering pickle ball, beach, kids playground and lots more. brbrOCEANSIDE IS A NEW DEVELOPED COMMUNITY AND THERE IS SOME TEMPORARY CONSTRUCTION ONGOING ON THE LAST TWO HOMES CLOSEST TO BEACH CONFINED TO SPECIFIC AREAS BUT THERE IS NO ACCESS TO BEACH/PIER CURRENTLY. DURING THIS TIME WE ARE OFFERING GUESTS PASSES TO THE ISLANDER RESORT STEPS FROM OUR PROPERTY. PLEASE INQUIRE WITH HOST. APOLOGIZE FOR THIS TEMPORARY INCONVENIENCE AND REST ASSURED IT WILL NOT AFFECT YOUR VACATION EXPERIENCE. brbrVisit Islamorada Chamber of Commerce website for calendar and list of local events.brhttps://islamoradachamber.com/brbrNotable residents of Islamorada:brInclude Miguel Cabrera, Gene Hackman, Jimmy Johnson, and Ted Williams. If you think the area looks familiar, you may recognize it from the Netflix TV Series BLOODLINE which was filmed in Islamorada.brbrIslamorada is known as the Sport-Fishing Capital of the World. And recently the island was named one of the 17 most romantic destinations in the U.S.brbrIf you are interested in golf carts this is their site islamoradaluxurycarts.com 305-394-5350 for rentals, let them know we sent you. There is also a Freebee transportation .You can download it in the App Store to get you around for free. brbrThere are also bike and kayak rentals nearby as well as fishing charters, boat tours, tiki tours, water sports, etc. All info is in the welcome binder in the house.

Book Now! Discounted Pricing Last Minute Availability

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$2185.14

Wander Islamorada Retreat offers an exceptional collection of amenities designed for comfort, entertainment, and relaxation. Outside, guests can enjoy a stunning heated waterfront pool surrounded by a tropical lounge area and a tiki cabana for shaded relaxation. The property features a 35-foot-wide deep-water dock, perfect for accommodating larger boats—an especially valuable feature for Islamorada travelers looking to explore the Keys by water or enjoy world-class fishing and boating. Guests also have access to two paddleboards and two kayaks for on-the-water adventures, as well as ample parking with dedicated boat trailer space. Additional conveniences include laundry facilities, elegant indoor and outdoor dining areas, and thoughtfully designed spaces that blend island charm with elevated comfort.brbrSet in the heart of the Florida Keys, this area offers endless opportunities for relaxation and adventure. Spend your days snorkeling or diving in the crystal-clear waters of the nearby reefs, kayaking through mangrove tunnels, or embarking on a world-class fishing excursion in the sportfishing capital of the world. Explore the local marinas, art galleries, and boutiques that showcase the island’s creative spirit, or enjoy fresh seafood and tropical cocktails at vibrant waterfront restaurants. For a touch of nature, visit the nearby parks and beaches for paddleboarding, sunset walks, and dolphin spotting.brbrHOUSE RULESbrHosting parties and events is prohibited in this home.brbrPET POLICYbrOur pet fee is $350/stay charged at check-out. The fee goes to the cleaner for the extra work required after a pet stays. Pets are strictly prohibited in beds, indoor or outdoor furniture, or spa facilities. Pet owners will be responsible for damage and charged through their payment on file.

Islamorada Retreat / Waterfront, Pool & Boat Dock

Islamorada, Florida, United States

7

Bed

5

Bath

15

Sleeps

$1274.87

Experience the ultimate coastal getaway at this spectacular 5 bedroom, 5.5 bathroom oceanfront home, complete with deep water dockage. This stunning retreat offers the perfect blend of elegance and entertainment, making it an ideal destination for families and friends. brbrStep inside to find an open concept living space bathed in natural light. The kitchen is a chef's dream, equipped with top-of-the-line appliances, a large island, and plenty of counter space. The spacious dining area and cozy living room provide the perfect settings for gatherings and relaxation. Relax and watch the ocean's movements from the comfort of your couch, with expansive windows leading to a balcony right off the living room. brbrEach of the five bedrooms is a private sanctuary, offering luxurious bedding, and stunning views. The master suite is a true retreat, with a private balcony, a spa-like bathroom, and a walk-in closet. brbrThe expansive outdoor area is designed for leisure and fun. Lounge by the pool, take a dip in the hot tub, or enjoy a morning cup of coffee while enjoying the sunrise and ocean breeze. The deep water dockage invites you to explore the sea, and the rooftop putting green offers a unique spot for entertainment.brbrThis oceanfront luxury home promises an unforgettable vacation experience, combining top-tier amenities with the natural beauty of the coast. Whether you're seeking adventure or relaxation, this stunning retreat provides everything you need for a perfect getaway. Book now and start creating lasting memories in this idyllic paradise!

Stunning 5-bedroom Ocean's Edge home in Tavernier, perfect for up to 10 guests.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$266.7

Gorgeous and highly appointed luxury Island villa with beach access. You are right in the middle of it all with this perfect location. Walk or bike to some of the best restaurants and shopping Islamorada has to offer.

Best Location in Islamorada!! Beach access - Boat trailer parking!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$409.07

Welcome to your home away from home in Islamorada, the heart of the Florida Keys. This beautifully designed two-bedroom, two-bathroom residence offers a perfect blend of comfort, style, and convenience in a world-class resort setting. Fully furnished with thoughtful coastal décor, this home invites guests to unwind, relax, and enjoy the serene rhythm of island life. All you need to bring are your flip-flops, sunscreen, and plenty of beach towels—everything else is already here, ready for your stay.brbrFrom the moment you arrive, you’ll be surrounded by the laid-back luxury and scenic beauty that make Islamorada one of the most desirable destinations in the Florida Keys. This residence provides all the essentials for a long-term stay, including a fully equipped kitchen, modern appliances, in-unit laundry, and spacious living areas designed for comfort and connection. With two full bathrooms and generous bedrooms, the home easily accommodates up to six guests, making it ideal for couples, families, or friends traveling together. Every corner of the space reflects coastal elegance, from its soothing color palette to the relaxing island-inspired furnishings.brbrGuests enjoy full access to all resort amenities during their stay. Spend your days lounging by the waterfront resort-style heated swimming pool, or soak up the sun in the oceanfront tanning area where the seabreeze and gentle waves create the ultimate relaxation experience. The resort also features a clubhouse for gatherings, billiards tables, and an outdoor game lawn—perfect for enjoying a casual afternoon with family and friends. For those who love adventure, complimentary kayaks and paddleboards are available, offering the perfect opportunity to explore the turquoise waters surrounding the resort.brbrThe resort’s oceanfront boardwalk provides the perfect place to enjoy morning coffee or an evening stroll as the sun rises or sets over the Atlantic. Whether you prefer quiet moments of reflection or engaging in community activities, this property offers the best of both worlds. The resort’s social calendar is full of events for guests looking to connect with others, yet the peaceful layout ensures that solitude is never far away.brbrJust beyond the resort, you’ll find the charm and culture that make Islamorada so special. Known as the Sport Fishing Capital of the World, the area offers endless opportunities for anglers of all levels—from backcountry flats fishing to deep-sea charters in the open ocean. For water enthusiasts, Islamorada’s reefs and mangroves invite exploration through snorkeling, scuba diving, and eco-tours that highlight the area’s vibrant marine life and clear waters.brbrWhen it’s time to dine, Islamorada offers an impressive variety of options—from fresh seafood and local favorites to fine dining and waterfront cocktails. Many restaurants will even cook your catch after a day of fishing, giving you a true Keys-style dining experience. Within minutes of the property, you’ll find local gems serving everything from sushi and tacos to elegant oceanfront cuisine, ensuring there’s something for every palate.brbrFounders Park, located directly across the street from the resort, is one of Islamorada’s best-kept secrets. This beautiful public park features a sandy beach, swimming area, walking and biking trails, a marina, and pickleball and tennis courts. It’s an ideal destination for guests looking to stay active, enjoy a day by the water, or take in the scenic beauty of the Keys. Whether you want to spend your day lounging on the beach or participating in community recreation, Founders Park provides the perfect complement to your resort experience.brbrInside your home, you’ll find a warm and inviting atmosphere that makes it easy to settle in. The open-concept living area is perfect for entertaining or simply relaxing after a day in the sun. The kitchen comes fully equipped with stainless steel appliances, solid surface countertops, and all the cookware and utensils needed to prepare meals with ease. The dining area flows naturally into the living room, where large windows allow natural light to fill the space and bring in the beauty of the surrounding landscape.brbrEach bedroom is comfortably furnished with quality bedding and ample storage, providing guests with their own peaceful retreat. The two full bathrooms are modern, bright, and equipped with all the essentials you’ll need during your stay. The inclusion of a washer and dryer adds an extra level of convenience, especially for extended stays.brbrGuests who choose to work remotely during their visit will find a peaceful and inspiring environment that’s well-suited for productivity. The home’s layout provides quiet nooks and comfortable seating areas, along with high-speed internet access to ensure a seamless experience for remote work or streaming entertainment.brbrThis home’s elevated design also enhances the view and provides peace of mind with its hurricane-rated construction. You can relax on your balcony or patio and enjoy a mix of ocean glimpses and stunning views of the resort’s landscaped grounds, complete with tropical palm trees, bright flowers, and gently swaying sea breezes. The location provides just the right balance of tranquility and convenience, with easy access to all resort amenities and the best of Islamorada.brbrGuests will appreciate that this property is part of a secure, well-maintained resort community that offers both privacy and connection. Whether you’re here to unwind, explore, or simply enjoy the island lifestyle, this home provides everything you need for a memorable extended stay.brbrA minimum stay of 28 nights is required for this property, making it ideal for those seeking a month-long retreat or an extended seasonal getaway. The home is designed for guests looking for more than just a vacation—it’s for those who want to experience what it truly means to live in the Florida Keys. From morning sunrises to peaceful evenings by the water, every moment here embodies the beauty of island living.brbrCome experience the best of Islamorada in a home that offers both comfort and character. With full resort access, modern amenities, and proximity to beaches, dining, and outdoor recreation, this is the perfect destination for guests who want to combine relaxation, adventure, and the timeless charm of the Florida Keys. Whether you’re visiting for a month or for the season, you’ll quickly discover why life moves a little slower, smiles last a little longer, and every day feels like paradise in Islamorada.brbrMinimum stay: 28 nights. Reservations are now being accepted for guests seeking an extended stay in a resort community that perfectly blends privacy, convenience, and the magic of the Florida Keys.

Pet Friendly 2BR/2BA Steps from the Water’s Edge with Unparalleled Sunrises

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1109.35

Welcome to your private oceanfront retreat in Islamorada, Florida Keys. Located in the exclusive gated community of Angler's Reef, this spacious 4-bedroom, 3-bath waterfront vacation home includes a private 31-foot boat slip at no additional cost, stunning Atlantic Ocean views, direct beach access, a resort-style pool, and a newly renovated gourmet kitchen.brbrWhether you're planning a family vacation, fishing trip in the Fishing Capital of the World, boating adventure, or relaxing Florida Keys getaway, this home offers the perfect combination of luxury, comfort, and convenience.brbrWhy Guests Love This Homebrbr✓ Private 31' Boat Slip Included (No Extra Fee)brBring your boat and enjoy easy access to some of the best offshore fishing, reef fishing, backcountry fishing, diving, and snorkeling in the Florida Keys. Your protected private marina slip is just steps from the home, making it easy to head out on the water whenever you choose.brbr✓ Prime Oceanfront LocationbrWake up to breathtaking Atlantic Ocean sunrises and panoramic water views from multiple private balconies and wraparound porches. Enjoy morning coffee overlooking the water or unwind with a sunset cocktail after a day on the boat.brbr✓ Resort AmenitiesbrGuests enjoy access to Angler's Reef's oceanfront swimming pool, sandy beach, marina, and beautifully maintained tropical grounds. Complimentary kayaks and paddleboards are available for exploring the nearby waters and sandbars.brbrThe HomebrDesigned for families and groups, this two-story coastal home comfortably accommodates up to 8 guests.brbrMain LevelbrThe open-concept living area is bright, spacious, and designed to maximize the spectacular ocean views.brbrFeatures include:br• Newly renovated gourmet kitchenbr• Viking stainless steel appliancesbr• Stone countertopsbr• Wine coolerbr• Large pantrybr• Expansive dining areabr• Comfortable waterfront living roombr• Queen bedroombr• Full bathroombr• Washer and dryerbrbrLarge wraparound porches extend the living space outdoors, creating the perfect setting for dining, entertaining, or simply enjoying the ocean breeze.brbrSecond Level: The upper floor includes three additional bedrooms:brbrPrimary Suitebr• King bedbr• Private ensuite bathroom with dual sinksbr• Private covered balconybr• Panoramic Atlantic Ocean viewsbrbrGuest Bedroombr• King bedbr• Balcony accessbr• Ocean viewsbrbrGuest Bedroombr• Queen bedbr• Balcony access in hallwaybrbrA full shared bathroom serves the guest bedrooms.brbrAngler's Reef CommunitybrAngler's Reef is one of Islamorada's most desirable gated waterfront communities, known for its private marina, tropical landscaping, oceanfront pool, and convenient location.brbrNearby activities include:br• World-class sportfishing and charter fishingbr• Offshore and reef fishingbr• Snorkeling and scuba divingbr• Sandbar excursionsbr• Paddleboarding and kayakingbr• Dolphin encountersbr• Waterfront diningbr• Sunset cruisesbr• State parks and nature trailsbrbrYou'll be just minutes from many of Islamorada's most popular restaurants, marinas, breweries, and attractions.brbrIncluded with Your Staybr• Private 31' boat slip (#21)br• Oceanfront community poolbr• Sandy beach accessbr• Kayaks and paddleboardsbr• High-speed Wi-Fibr• Washer and dryerbr• Free parking for 2-3 vehiclesbr• Fully equipped gourmet kitchenbr• Multiple ocean-view balconies and porchesbrbrGuest FavoritesbrEasy dockage for our 31-foot boat.brThe sunrise views from the upper porch were incredible.brPerfect home base for our family fishing vacation.brbrCheck-In: 4:00 PMbrbrBook your Islamorada waterfront vacation today and experience why guests return year after year to enjoy the boating, fishing, and laid-back luxury of the Florida Keys.

Oceanfront 4BR Retreat w/ Private 31' Boat Slip, Pool & Beach, gourmet kitchen

Islamorada, Florida, United States

Bed

Bath

Sleeps

$695.54

This Beautifully renovated Compound / Property Comes With A recently completed and Magnificent Landscape Oasis , That Begins With the Coral Stones And Fire Bowl Entrance To A Large Golf Putting Green For Everyone In The Family To Enjoy ⛳️, Plenty Of Shaded Areas With Palm Trees a Coral stone Fire Pit and Hammock area With Comfortable Sittings that’s just perfect For Family Gatherings and fishing stories , (including the one that got away) and/or just total relaxation . and Much More . Truly The Perfect Vacation Home For Any Size Family. .Has 3 distinct Sleeping Quarters ,one in the Upper Floor Home ( This Spacious And Accommodating 2nd Floor Suite have its Own Entrance ,King Size Bed , Small Fridge/ Microwave Oven , Nespreso Coffee Maker , Sitting Vanity With Mirror , A 65 In TV And A Large Confortable Scenic And Relaxing Wrap - Around Balcony ). On Ground Floor and With Access from the Swimming Pool Area ,you’ll find Entrance to an Area With Two Beautiful Bedrooms With Queen Size Beds and One Full Bathroom all Attached to The Main house Also On Ground Floor That Have 3 Bedrooms, one of them a Master Bedroom With double Glass Doors , 65 inch TV and direct access and views to Swimming Pool And Harbor. Additionally, Two Full Bathrooms Large Kitchen and Living room with Wall/entertainment unit and a 65 in TV . .Sleep 10-12 Comfortably. Compound located in a Magnificent and rare Canal End With An Extended Waterfront View. Easy Access To Best Hidden Beach In Islamorada With Otherwise no Access to Public except by Boat, It’s Only 3-4 min by Power Boat vs 15 Min Of A Breathtaking Scenery Kayaking ( kayaks provided with the property ) Along The Coast. Enjoying Nature At It’s Best ,Watch The Abundance Of Pelicans, Playing And Passing Dolphins And Gentle Manatees On Your Way. Only 5 Min By Boat To Atlantic Ocean And 15 Min To The World Famous Alligator Reef For Some Of The Best Snorkeling The Florida Keys Have To Offer, There’s Also Anne’s Beach Only 1/4 miles Walking Distance .Enjoy The Newly Build Lagoon Shape Swimming Pool And Tiki Hut For A Refreshing Cocktail Or BBQ . Don’t Feel Like Cooking No Problem , Local Restaurant With Great Food Just short Walking Distance. Yes This Wonderful Property Has It All For A Memorable And Relaxing Vacation. 135 feet of Dockage Good For Multiple Boats .1hour 25 min from Miami Airport, 1hour 25 min from key west. ( New Updated Pictures To Follow Soon ).

Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home

Islamorada, Florida, United States

6

Bed

Bath

12

Sleeps

$521.27

Beautiful coastal boho-style home located in the highly sought-after Venetian Shores neighborhood of Islamorada. This spacious waterfront property offers plenty of dockage and quick access to both the Atlantic Ocean and Florida Bay via Snake Creek, making it a great choice for guests bringing a boat. The dock is equipped with shore power, water, and a fish cleaning station, making it easy to rinse down the boat and prep your catch after a day on the water. Islamarina is conveniently located right at the entrance of the neighborhood, where you can grab fuel, bait, and other essentials before heading out.brbrThe home features a flexible layout with two bedrooms and one bathroom downstairs along with a convenient kitchenette, while the upstairs offers two bedrooms and two bathrooms with the main living space and kitchen.brbrJust off the upstairs living room, you'll find a cute porch with a swing, the perfect spot to relax with your morning coffee or unwind in the evening while enjoying the island breeze.brbrDownstairs, the outdoor space is designed for relaxing after a day on the water, featuring sun loungers, a fire pit, and an in-ground spa, creating your own private Keys-style retreat.brbrWith its relaxed coastal boho style, excellent boating access, and inviting outdoor spaces, this Venetian Shores home is the perfect place to experience the laid-back Islamorada lifestyle.brIf booking more than a year in advance current prices may not reflect the 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. brPlease 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.

Spacious 4-bedroom canal home in Islamorada, perfect for families or groups.

Islamorada, Florida, United States