Vacation Home Rentals By Owner In Islamorada, FL

The ocean is your front yard at this modern, luxurious townhome hidden away in a small, private seaside community. Enjoy the pool, the beach, the dock and the peacocks! Walk to restaurants or cook at home on your private grill. We are work-from-vacation-home friendly with desk, chair, high speed wifi. Amazing fishing, boating, sightseeing, relaxing and dining experiences are all around you here, come visit and invent your perfect vacation!brbrWelcome to your oceanfront townhome on Millionaire's Row in Islamorada, the Sport Fishing Capital of the World! Take in the sweeping ocean views on every level from the living room, the master bedroom, the screened porches and the rooftop deck. Enjoy the front yard sunrise in the morning and moonrise at night. Amazing bayside sunsets await you on the rooftop deck.brbrYour newly remodeled modern kitchen is equipped with every convenience including stainless appliances, a washer and a dryer, restaurant quality cookware and cutlery (yes, sharp knives and cutting boards!), full place settings for 8 and a large family table. Small appliances include a drip coffee maker, Keurig coffee maker, 4-slice toaster, blender, mixer, slow-cookers. Downstairs you'll find a private 3-burner gas grill with extra propane.brbrNeed to work on your vacation Pop up your desk and pull up your swivel chair anywhere you like, connect to the 100Mbps wifi and enjoy the ocean view.brbrYou'll find big-screen flat panel TVs in the living room and the bedrooms, each equipped with a Roku. Watch cable channels, hundreds of on-demand movies and shows, stream Netflix, Disney, Apple+, etc. A wall-mounted iPad in the kitchen handles TV and streaming duties as well as weather/wind/tide forecasts, recipes, news, sports.brbrThere are hundreds of dining experiences to choose from within minutes of your location, from outdoor picnic tables to ocean- or bay-front verandas to indoor dining and everything in between. Brunch, food trucks, seafood, Italian, pizza, sushi, diner counter seating, white-linen fine dining... Islamorada has it all.brbrYou'll have a guest pass for Founders Park, just a mile south of your townhome bayside. Enjoy the sandy beach, swim or snorkel with colorful fish, visit the olympic pool and the splash park. You'll also have access to the pickle ball and tennis courts, the running trails, the ball fields, batting and golf cages, and the hammock hiking trails.

Peacock Shores Islamorada - Vacation On The Beach!

Islamorada, Florida, United States

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Bath

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$403.45

Sea Glass Cottage 2b 2b canal front home.brbrBring your boat or two, and enjoy your vacation or holiday relaxing and playing in the world famous Florida Keys. The Sea Glass cottage, is a beautiful canal front, keys style home on a over sized corner lot with ample parking for guests. The cottage provides our guests with direct bay or ocean access in minutes via Tavernier Creek. brbrIt is centrally located and close to Tavernier Creek Marina, a 10-acre facility that provides boat access to a full service marina. In addition, you can grab some delicious Cuban cuisine at Habanos On The Creek, fuel up or service your boat at the marina, or grab your bait supplies at Chris's Bait and Tackle for a fantastic day of fishing, diving or just enjoying the turquoise waters of the beautiful Florida Keys. brbrThe Sea Glass Cottage boasts 2 bedrooms and 2 baths. Completely remodeled with all upgraded finishes throughout. Features include beautiful cottage style wood like flooring throughout, new cottage style kitchen with built in dining, stocked coffee bar and adjacent seating to relax in the morning or evening, beautifully decorated living room with fireplace with access to patio, master bedroom located directly off front patio providing beautiful morning sunrise views. Master features a king size bed, walk in closet and completely remodeled and upgraded private bath with shower. Guest bedroom provides cottage style furnishings with comfortable queen size bed and full size sleeper sofa with view to the canal. Guest bath also completely remodeled with new cottage style decor and bathtub. brbrThe house has two separate docks that have been completely replaced and rebuilt with top of the line decking, that will accommodate up to a 60ft boat and the other up to 20ft. Never run out of space for your toys. Fish cleaning station and covered outdoor seating area to relax. Downstairs storage room provides ample space to store fishing gear, bikes, etc. brbr4 adult size brand new Panama Jack beach cruisers are available for use during your stay along with 2 adult size kayaks and 2 children's kayaks.brbrOutdoor showerbrbrNeighborhood park with kayak launching rampsbrbrMonthly and seasonal rentals welcome. brbrLocated in a well established, quiet family neighborhood. Please respect our neighbors. Guest are asked to refrain from loud parties, no destructive behavior or drugs!!! If police are called to residence during your stay, you will be ask to leave and forfeit remaining rent. Renters are responsible for cleanliness of home during your rental stay. brbrArea is perfect for walking, jogging, biking and kayaking. There is a small neighborhood grocery store with a great selection of meats and wines, BB&T bank, restaurant/bar, gas station and marina within walking distance from the residence. Additionally, there are several restaurants, dress and gift shops, dive center, paddle board and kayak rentals, dive and fish charters, seafood store, church, and a once a week farmers market.brbrThere is also a shopping center which includes Winn-Dixie, restaurants, bar, post office, movie theater, CVS, McDonald's, Dunkin Doughnuts, AT&T and Mariners Baptist Hospital. 3 miles from the house is Founders Community park with beach, playground, soccer field, outdoor gym, tennis courts, boat ramp and swimming pool.brbrCome and enjoy the wonders of the Florida keys. 28 Day minimum rentalbrbrThe Sea Glass Cottage boasts 2 bedrooms and 2 baths. Completely remodeled with all upgraded finishes throughout. Features include beautiful cottage style wood like flooring throughout, new cottage style kitchen with built in dining for 8, coffee bar and adjacent seating to relax in the morning or evening, beautifully decorated living room with fireplace with access to patio, master bedroom located directly off front patio providing beautiful morning sunrise views. Master features a king size bed, walk in closet and completely remodeled and upgraded private bath with shower. Guest bedroom provides cottage style furnishings with comfortable queen size bed and sleeper sofa with view to the canal. Guest bath also completely remodeled with new cottage style decor and bathtub.brbrKahiki Harbour is a well established, quiet family neighborhood. Please respect our neighbors. Guest are asked to refrain from loud parties, no destructive behavior or drugs!!! If police are called to residence during your stay, you will be ask to leave and forfeit remaining rent. Renters are responsible for cleanliness of home during your rental stay. Owner will be responsible for yard maintenance.brbrArea is perfect for walking, jogging and biking. (bikes provided) There is a small neighborhood grocery store with a great selection of meats and wines, BB&T bank, restaurant/bar, gas station and marina within walking distance from the residence. Additionally across from Kahiki Harbour {rt 1} there are several restaurants, dress and gift shops, dive center, paddle board and kayak rentals, dive and fish charters, seafood store, church, and a once a week produce and market.brbrWith-in one mile from neighborhood there is also a shopping center which includes Winn-Dixie, restaurants, bar, post office, movie theater, CVS, McDonald's, Dunkin Doughnuts, AT&T and Mariners Baptist Hospital. 2 miles from the house is Founders Community park with beach, boat ramp and swimming pool.brbrCome and enjoy the wonders of the Florida keys.

Sea Glass Cottage Beautiful Canal Front Home

Islamorada, Florida, United States

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Sleeps

$913.87

Village of Islamorada - Vacation Rental License No. 24-0248brbrThis home is remodeled every year in some way or form...We try to make it interesting and fun particularly for our repeat customers. Our objective is to provide the most rewarding and awesome experience possible. From the most comfortable beds you can find, to the various cooking options and outdoor eating choices. You can pretty much live outside with all the amenities for outdoor living provided at this vacation rental. brbrThis property is NOT AVAILABLE for any special events including WEDDINGSbrbr

Private Beachfront Paradise

Islamorada, Florida, United States

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Bath

Sleeps

$223.34

It's not every day that you come across a rental like this. This delightful and fun 2 bedroom, 1.5 located in Lower Matecumbe offers a private beach, dockage, and enough charm as you can squeeze in. brbrThe main living space, located on the second floor, has a great open layout making it the perfect space to both entertain and unwind after a long day on the water. With wall-to-wall windows, peekaboo bay views, lively and fun décor, charming wood accents this condo is the perfect home away from home. The third floor offers a guest bedroom with two twin beds, bathroom, and master bedroom with a cozy reading nook and windows with the perfect bay view. The laid-back yet eclectic vibe of this home is gratifying to all and must be experienced.brbrEnjoy your own little slice of paradise from the beach. One of the very few beaches in the Florida Keys, Sandy Pointe offers soft sand, crystal clear waters, and the best sunsets on the island. Feeling more adventurous Hop on your boat and go fishing or take a boat ride to lunch. Placed in one of the most desirable boating locations, you are minutes away from some of the best fishing spots in the world. Enjoy backcountry fishing right in your backyard or hop over to the oceanside via Channel 5 Bridge. brbrLocated in one of Lower Matecumbe's favorite neighborhoods, Sandy Pointe is only minutes away from downtown Islamorada and Marathon. brbr28 day minimum, please inquire for rates and availability. brbrDockage is available on a first come first serve basis. 30' max length. brbrSandy Pointe 108 ~ MM74 Bayside

Zesty Lower Matecumbe Condo with Private Beach & Dockage

Islamorada, Florida, United States

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Sleeps

$675.0

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.brbrUpstairs there are three bedrooms and two baths. Downstairs there is a totally independent, one-bedroom, one-bath apartment. The house is PERFECT for those traveling with different age groups, in-laws, teenagers, or two families. The house is fully equipped with everything you will need to make your vacation a 'PERFECT' one.brbrSpend your days soaking up the sun and your evenings relaxing in the jacuzzi or in our HEATED swimming pool. THIS IS PARADISE! Being just one-and-one-half hour from Miami and one-and-one-half hour from Key West, you can easily spend a full day in either of the two, and be back on time to watch the beautiful sunset.brbrWe are just one mile from world-famous Holiday Isles, TIKI BAR. There you can sit out by the beach, or take a dip in the pool. Their live entertainment and contests give your vacation the full island effect. As if diving, snorkeling, sunning, boating, and swimming all day were not enough, do not forget to spend an afternoon swimming with the dolphins or the stingrays. Also, just one minute from the house.brbrCome and spend you PERFECT vacation at THE PERFECT GETAWAY!!!brbrPOOL HEATING WEEKLY CHARGE OF $300 AVAILABLE UPON REQUEST. RENTER MUST NOTIFY OWNER AND PAY FOR HEATING CHARGE IN ADVANCE TO ASSURE THAT POOL IS HEATED IN ADVANCE. AFTER CHECK IN, POOL HEATING CHARGE IS $400, AS POOL COMPANY HAS TO RETURN TO LOCATION TO TURN ON THE HEATER.brbrBOAT AVAILABLE FOR RENT. ARRANGEMENTS MUST BE MADE IN ADVANCE.

The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip

Islamorada, Florida, United States

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Sleeps

$1510.57

OSPREY BAY VILLA – Your private bayfront escape in the heart of Islamorada, Florida Keys! brbrRelax and enjoy incredible panoramic bay and sunset views from this elegant yet casual Old Keys Charm home, designed for the perfect family or group getaway. With a heated pool, hot tub, and deep-water dock, you’ll experience the best of island living—whether you’re soaking up the sun, exploring by boat, or strolling to local restaurants and shops.brbrKEY FEATURES:brbr*5 bedrooms, sleeps 10–12 guestsbr - 2 king bedrooms (including master suite)br - 1 queen bedroombr - 2 bedrooms with 2 queen bedsbr* 3 full bathroomsbr - Master bath with separate vanity roombr - Full bath with bathtub + separate shower, double sinksbr - Pool-level bath with shower + direct outdoor accessbr* Fully equipped gourmet kitchen with open dining room and atrium gardenbr* Spacious living room with coral rock fireplace + wet barbr* Second-level master suite with private bayfront veranda + fireplacebr* Multiple sunning decks, heated pool, and hot tubbr* Deep-water dock + boat basin (perfect for boating, snorkeling, kayaking & paddleboarding)br* Lush tropical landscaping + private sandy beach area for wadingbr* Incredible sunset views from expansive waterfront lawn and outdoor spacesbr* Secluded yet walkable to iconic Islamorada restaurants and local shopsbrbrCome, Relax & Enjoy!brYour perfect Florida Keys vacation awaits.

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

Islamorada, Florida, United States

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Bath

Sleeps

$694.42

Experience waterfront FL Keys living at its finest at The Seascape, a modern, newly constructed retreat nestled directly on the ocean where every morning begins in color, and every evening ends in calm. Here, the ocean isn’t just a view. It’s a presence. Come make memories at Islamorada's iconic tiki bar sandbar, legendary fishery, or gather on sunlit shores to relax and revel in life’s simplest joys with stunning views, direct water access, and a stylish escape from the everyday.brbrLocated in a secure, gated enclave, The Seascape provides one of the closest waterfront experiences available in the Florida Keys, complete with private dockage and sweeping ocean views. Spanning over 2,000 square feet, this spacious three-bedroom residence boasts two expansive oceanview balconies, a private exclusive entertainment lounge, and interiors curated for both relaxation and refined living. Whether you’re planning a family vacation or a retreat with friends, The Seascape is your launch point for making lifelong memories. Keep your eyes open for dolphins, manatees, and pelicans, or gaze across the water toward the iconic Alligator Reef Lighthouse and Islamorada Sandbar.brbrStylish Interiors with the Comforts of Home in MindbrThe Seascape was designed for both relaxation and entertainment, featuring:br✔ Two large balconies overlooking the ocean—perfect for outdoor dining, a morning coffee or an evening glass of winebr✔ A fully stocked designer kitchen with stainless steel KitchenAid appliancesbr✔ A bright living area with oversized sectional seating and a 65 OLED 4K TVbr✔ Thoughtful details and elegant decor throughout every roombrbrThree Private Tranquil Bedrooms with Room for Everyonebr✔ Primary Suite – King bed, private patio that extends the bedroom to the ocean front with comfortable egg chairs, and ensuite bath with a walk-in rainfall shower br✔ Second Bedroom – King bed with ensuite bath with a walk-in rainfall shower br✔ Third Bedroom – Ideal for kids or additional guests, featuring a full-size bunk bed with a pull-out trundle and ensuite bath with a walk-in rainfall showerbrbrBonus Entertainment Space – Exclusive to This HomebrUnwind in your private lower-level entertainment retreat, complete with:br✔ 55 4K Smart TV with gaming systembr✔ Ping pong table, pop a shot, mini-putt matt, board games, books, and morebr✔ Lounge area with sectional seating and bean bagsbr✔ Outdoor games like cornhole for fun in the sunbrbrPool, Private Dockage & Water Gear Includedbr✔ Dock space for boats up to 26 ft (advance reservation required)br✔ Kayaks and paddleboards available for guest usebr✔ Enjoy the community’s heated oceanfront pool with lounge chairs and a sun shelfbr*Options for nearby trailer storage will be provided since we cannot accommodate trailers onsite.brbrNearby Attractions Include:br✔ Feed the tarpon at Robbie’s Marinabr✔ Visit dolphins and sea lions at the walkable Theater of the Seabr✔ Snorkel vibrant coral reefs and local shipwrecksbr✔ Offshore fishing charters at nearby Bud n Mary's and whale Harbor marina to best enjoy the sportfishing capital of the worldbr✔ Relax at Islamorada Library Beach or Founders Park (free guest access!)br✔ Explore the charming shops and galleries of Morada WaybrbrThis awesome home comes with AC, a washing machine, WiFi, heating, and even a fitness room. With 3 bathrooms and a hair dryer, guests will have everything they need for a comfortable stay. Our place is equipped for both long or short stays to make your holiday one to remember.

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

Islamorada, Florida, United States

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Bath

Sleeps

$412.72

Windley Cottage is a welcoming, tastefully-decorated home located at mile marker 85. It's away from the highway, and just steps from the pool and docks. The “Bahamian conch style home provides irresistible charm and comfort tucked in among lush landscaping. Angler's Reef is centrally located, perfect for exploring all of the Florida Keys!brWhether you’re looking for a couples’ retreat or an exciting Keys experience with the family, this home is the answer! Flexible bed arrangements. Call 239-250-4135 for more information. IbrWe have amenities for all ages! Enjoy a swim in our temperature-controlled pool. Paddle out to the sandbar on our complimentary paddle boards or kayaks. Cycle to the many gift shops and restaurants. Scuba or snorkel the nearby coral reefs and shipwrecks, rich with underwater wonders. Dive near the popular Alligator Reef Lighthouse, which is visible and easily accessible from Angler's Reef. For a fee, dock your boat in our protected lagoon with direct, deep-channel access on the Atlantic. Nearby marinas offer boat/jet ski rentals, fishing/scuba/snorkeling charters, and party boats for fun on the water. Whether you fish from shore or our docks, flats-fish in the back bays, or deep-water fish for big game, Islamorada has it all! Swim with the dolphins and learn about the local marine life at Theater of the Sea (1/2 mile from our home). Dine at one of the fabulous nearby restaurants, many offering nightly entertainment.brbrJust 2 miles north is Islamorada Founders Park at MM 87 Bayside. The park offers a shallow water beach, ball fields, playground, fishing jetty, driving cage, 3 paddle ball courts, bocce, tennis, a large playground, basketball courts, an exercise course with 18 stations, and a multi-purpose path within the 40-acre park. brbrOther municipal parks include the Islamorada Library Beach and Anne’s Beach. The Windley Key State Geological Site, a state park, is a former coral rock quarry, where fossils of sea creatures can be seen throughout the park.brbrAfter a busy day, enjoy a glass of wine on one of our two private beaches. Play a board game on the back porch. Dim the pendant lights in the great room and turn on the fireplace as you cuddle up to watch your favorite movie after a busy day. brbr Just pack a few clothes and your toothbrush and head down to the Florida Keys for the vacation of a lifetime in the comfort and luxury of Windley Cottage! See why people from all over the world get sand in their toes and return here again and again!brbr Contactless check-in and check-out is on Saturdays. Please contact us if you want a different day. Our calendar is updated in real-time and posted rates are accurate. brbrSTR#-24-0163brFL DBPR #DWE5403337brbrNOTE: We also own a vacation rental property on Cape Cod, MA. Visit Vrbo listing 3757615 for photos and further information of this property.

OCEANSIDE ANGLERS REEF HOME- Gated Community with Pool, Dock, Private Beach

Islamorada, Florida, United States

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Bath

Sleeps

$679.26

Sure you can drive another 1.5 hours to reach Marathon but why would you do that when the best restaurants and events are right here in Islamorada. Stay in a beautiful home in one of the best communities in the Florida Keys, Venetian Shores. You can watch from your veranda tarpons jumping, sea turtles, and manatees . Sip a cocktail and watch your favorite tv show in your own private pool, or hammock away your day while reading a good book. Creating delicious meals is easy using the outdoor kitchen and you will never have to go for an ice bag run because you have a big ice maker at your disposal. The best restaurants, dive shops, fishing spots, and entertainment is just minutes away. If you would like to stay for less time, that can be accommodated by charging you a monthly rate. We only rent monthly .

Endless Summer Awaits!

Islamorada, Florida, United States

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Sleeps

$273.06

Home is located in an ocean front resort. This 2 bedroom 2 bath home is pet friendly. Home has amazing views of the Atlantic Ocean. Home sleeps 4 persons and is designed to make its guests feel at home, offering upgraded features as in stainless steel appliances, a farm sink, quartz countertops, and plenty of storage. The floorplan has an open kitchen living floorplan and a private deck with awesome views.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.

Oceanview 2BR home in a pet-friendly resort! Minimum 28-Day Reservation Required

Islamorada, Florida, United States

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Bath

Sleeps

$567.26

Welcome to your ultimate Florida Keys dream getaway! This secluded home is perfectly located in the extremely desired gated neighborhood of Bay Hammock. Come enjoy this private tropical oasis, sipping cocktails by the pool or enjoying morning cups of coffee on the balconies. brbrAs you approach this home, the striking architecture and lush landscaping set the tone for your idyllic getaway. Stepping inside, you'll be greeted by an atmosphere of contemporary elegance, with thoughtfully designed spaces that blend seamlessly with the serene natural surroundings.brbrThe heart of this vacation rental is undoubtedly the stunning outdoor area. A private pool, enveloped by a meticulously landscaped tropical paradise, beckons you to unwind under Islamorada's warm sun. You can take a refreshing dip in the crystal-clear waters or bask in the sun on comfortable loungers that line the pool's edge. For the more adventurous, an outdoor kitchen and bar awaits overlooking the pool. Imagine savoring a sunset dinner by the pool and making memories that last forever gazing at the stars around the firepit.brbrBeyond the pool area, a private boat slip offers direct access to the waterways, making it effortless to explore Islamorada reefs or embark on fishing adventures.brbrWhether you're seeking a romantic getaway, a family vacation, or a gathering of friends, this vacation rental promises the utmost in comfort, style, and convenience. And within the safety of a gated neighborhood, you can rest assured that your privacy and security are a top priority.brbrYour dream vacation awaits at this hidden gem, where the beauty of the outdoors and the luxury of modern living combine to create an unforgettable experience.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.

Charming 3BR retreat in Islamorada, perfect for family getaways!

Islamorada, Florida, United States

3

Bed

Bath

Sleeps

$190.11

Make yourself at home in this 2-bedroom Islamorada townhome retreat. The space features a king bed and a 2 full beds, comfortably accommodating guests. With two bathrooms that include refreshing showers, getting ready is a breeze. Stay comfortable year-round with heating and air conditioning.. This lovely, peaceful townhome offers the perfect spot to unwind after a day of exploring. Kick back, relax, and enjoy everything Islamorada and our townhome has to offer.

Serene 2-bedroom townhome with AC in charming Islamorada

Islamorada, Florida, United States

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Sleeps

Select Dates for Price

This luxurious 4 bedroom, 3 bathroom house offers exceptional opportunity to experience the Florida keys in style with its flawless blend of coastal elegance and modern comforts. This property promises an unforgettable retreat for relaxation and adventure. Located in Lower Matecumbe key, mile marker 75, in the highly desired community of Port Antigua, this home has private access to one of the most desired beaches in the Florida Keys with its gorgeous white sand, tiki huts, picnic tables, grill and a private boat ramp makes this a great location to get away for a while. brbrThe main floor layout is open and ready for entertaining with its ping pong/pool table and kitchen island seating. There are four bedrooms with plenty of space to spread out. The two upper bedrooms are en suite style with bathrooms which includes the king bedroom and a double bunk beds room - a twin over full and another full over full. The main floor includes two more bedrooms which share a bathroom - a queen bedroom and other room has twin bunk beds with separate twin and trundle. House includes a total of 9 beds and sleeps 11 comfortably!brbrKitchen has been remodeled and updated with gourmet appliances including a wine/beverage cooler, toaster, Keurig coffee maker, and plenty of kitchenware and barware to entertain. Full washer/dryer.brbrOutdoors includes comfortable balcony seating area, BBQ and dock space for your boat. The property features dockage with a 20,000 lb lift for boat enthusiasts with direct access to the bay. Plenty of free parking and space in front for your boat trailer. brFree WIFI internet included with streaming access on all three TVs. brbrTo comply with local laws and HOA requirements, the minimum rental period is one month, and guests must be at least 25 years old to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.br

Port Antigua Retreat on Canal with Boat Lift and Private Beach Access

Islamorada, Florida, United States

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Bath

Sleeps

$705.38

141 LeSerra Lane - Located at mile marker 76, LeSerra Lane is a three-bedroom, two and a half bath oceanfront home that checks all the boxes needed to make your upcoming vacation the best yet! Enjoy your morning coffee watching the sun rise over the Atlantic Ocean. Jump in your boat and head out to some of the best fishing Islamorada has to offer or simply hang out by the private pool with a cocktail in hand and grill up your catch! We dare you to not have a good time at this property! VACATION RENTAL LICENSE: 24-0020 Please note, the pool is heated from Oct 1-April 1.brPer Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.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.

Relax in this 3BR open water view home with private pool in Islamorada.

Islamorada, Florida, United States

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Bath

Sleeps

$471.53

ANGLERS REEF is a quiet oceanfront community of Key West inspired homes, streets, and walking paths, that wind through a quaint village-style retreat. Located at Mile Marker 85 by Theater of the Sea, Windley Key Geographical Site, Snake Creek Marina & some of the best bars and restaurants in Islamorada.brbrGREAT LOCATIONbrThe house is in a quiet section of the community, away from the highway and just 2 homes from the ocean. Our porches are shaded and face a tree-lined yard with a view of the ocean.brbrOCEANFRONT RESORT-STYLE SWIMMING POOLbrThe pool is both heated & chilled so that it is always a perfect 87 degrees.brbrTWO PRIVATE SANDY BEACHESbrThe South Beach has a shoreline & ocean access. A tandem kayak sits on the beach for your use, (additional kayak, paddleboards, jet ski & boat rentals are available close by and available for drop-off to your beach or dock).brbrThe North Beach, a white sandy beach, is located just steps from the house.brbrDEEP WATER MARINAbrThe marina is just steps away from our house and is part of the community and enjoyed by all guests.brbrOUR HOUSEbrBuilt in 2007, this home, is bright and cheery with tile floors, high ceilings, and many large windows. It is newly decorated for the Keys and surrounded by lush tropical landscaping.brThe main floor has an open plan with, tile floors, granite counters, stainless appliances, flat screen TV w/DVD players, cable with PREMIUM CHANNELS, A DVR, Fast WiFi.brbrThere are 2 bedroom suites with flat screen TV’s and private baths located on the 2nd floor. Both baths have frameless glass showers and granite vanities. Rear bedroom has an ocean view and a private porch.brbrISLAMORADAbrParks in Islamorada, Village of Islands: Just 2 miles north is Islamorada Founders Park at MM 87 Bayside, which offers activity or relaxation for the whole family. An Olympic-sized pool with diving area, a shallow water beach, water sports rentals, ball fields, fishing jetty, bocce, tennis and basketball courts, vita course with 18 exercise stations, multi-purpose path, skate park and dog park all are within the 40-acre park. Fees may apply. Village municipal parks also include the Islamorada Library Beach and Anne’s Beach. There is the Windley Key State Geological Site, a state park, at the site of a former coral rock quarry. In addition to shady walks through unique foliage, fossils of sea creatures can be seen throughout the park. A free guidebook is available at the visitors center for use during your stay in the park. Islamorada also offers an 18-mile bicycle path that extends the length of the Village.brbrScuba/Snorkel!: Islamorada, long recognized as the 'Sport Fishing Capital of the World,' is now an icon among sport divers for a similar reason: a massive population of tropical marine life. High-profile coral heads and broad ledges shelter huge congregates of French grunt and goat fish, while regal queen angelfish casually graze amid the reef recesses. Friendly green moray eels swim freely along the spur-and-groove channels, and reclusive nurse sharks lurk beneath the overhangs. Islamorada offers a wide variety of shallow coral reefs, mini walls, shipwrecks, and even an underwater habitat for scientific research, the Aquarius. To learn more about Islamorada or any other manner of local lore, stop by the Chamber of Commerce at MM 82.5.

OCEAN VIEW ANGLERS REEF - POOL, BEACH. Walk or bike to local food + bars

Islamorada, Florida, United States

Bed

Bath

Sleeps

$397.74

This lovely oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500' of stunning private beach. Protected deep water marina (slip available at additional cost) with a deep channel out to the Atlantic. Single and Tandem Kayaks as well as Stand Up Paddleboards available for your use. Launch kayak from the private beach and try your luck at Islamorada's famed bone fishing in the flats right out front. Brand new in 2008, this home is fully equipped. Tile showers, Stainless appliances, granite kitchen counters, 3 Flat Screen TVs, & more! brbrIslamorada is the 'The Fishing Capital of the World' Great fishing in the gulf or ocean side. There are plenty of guides you can hook up with, as well as 'head boats' where you can walk on for a reasonable cost and fish the reef (just a few miles offshore). Bring your own boat or charter with a guide.Try your luck fishing right out front for bonefish, permit & barracuda on the flats. Or check out the mangroves for snapper and snook. Enjoy the views of the turquoise waters; swim in the large heated pool or just relax in the surrounding lush garden area overlooking the Atlantic; take a quiet stroll through the complex; take in some sun on the private beach. Restaurants: a short walk north is Hog Heaven (a night spot) and the Island Grill; a few miles south is upscale Pierre's on the Gulf and the more casual Islamorada Fishery next door (both are next to Worldwide Sportsman for fishing tackle, clothing, and a large indoor aquarium); also a few miles south is Holiday Isle, the Green Turtle Inn & many more eateries. Some other favorites are Ziggys and Maddogs, Morada Bay, Marker 88 and the famous Cheeca Lodge.Attractions: Theater of the Sea is about 1/2 mile south. Founders Park is just a mile or two north. Feed the Tarpon at Robbies, Boat and Wave Runners rentals within walking distance. We have second home listing 3788659 see for positive reviews. Saturday to Saturday rentals preferred and other options only considered off season. Vacation rental license # VR-281.br

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

Islamorada, Florida, United States

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Bath

Sleeps

$273.33

This home is in a resort. This is a 2bedroom 2bath home, Home has stunning views of the Atlantic Ocean. Home sleeps 6 and is designed to make all guests feel at home, offering upgraded features as in stainless steel appliances, a farm sink, quartz countertops, and plenty of storage. The floorplan has open kitchen living area a private deck with awesome views.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.

Oceanview 2 bedroom with jaw-dropping views! Min 28-Day Reservation Required

Islamorada, Florida, United States

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Bath

Sleeps

$380.62

Resort Style Venetian Shores Home with 70 ftbrDock on a 100 foot wide canal Completely remodeled. Two Bedrooms with King Bed, Queen bed and two pull out sofa beds. High speed Wifi, Two Flatscreen tvs, Two full Bathrooms. Beautiful walk around 360 porch with safty gates. BBQ Grill. 20,000 pound Boat lift. Relax with sunsets under the Tiki Hut. 5 min away from your local family sandbar and a mile away from Founders park. The closest boat ramp is founders park.

Islamorada waterfront villa

Islamorada, Florida, United States

Bed

Bath

Sleeps

$458.33

brBeautiful Key West Style home 2 BR 2 BA (en suites) + 1 HF BA Sleeps 6brIslamorada Vacation rental #24-3018brbr108 Anglers Way and boat slip (max 31') FOR EXTRA FEEbrbrCall Jennifer for more information 305-240-0592.brbrThere is no other neighborhood like Anglers Reef in Islamorada. It's beautiful Key West style pastel colored homes inside resort community, with garden like flora and fauna such as bougainvillea meticulously maintained, with a fantastic oceanfront swimming pool and boat docks and views over the Atlantic Ocean that will take your breath away. Just minutes from many local shops, bars and restaurants. Access to the ocean does not get any easier than at Anglers Reef.brThere Are 52 Homes at Angler's Reef With Only 36 Boat Slips. Our home has the option for you to bring your own boat and use the dock. It is a Safe, Gated Community with very little traffic, truly an oasis. Enjoy coffee or cocktail on one of four porches, (each bedroom upstairs has its own balcony and bathroom) Or enjoy the community Paddle Boards and Kayaks or just relax with a Netflix movie.brbrYou will tell you are someplace special when you see our 2-bedroom, 2.5-bathroom house, surrounded by wonderful landscaping, amazing palms, bougainvillea, and some of the most colorful tropical foliage that only the tropical Florida Keys can offer.brbrThe first floor offers a spacious, wide open layout with very comfortable couches. Granite counter tops, all updated appliances, kitchen is stocked with pots and pans, utensils plates, everything you will need to prepare anything. Stay entertained during your downtime by watching your programming of choice on any of the home’s 3 flat screen TVs with hulu subscription, or surf the web via the complimentary wireless internet access.brbrChildren of all ages will love the pool and the fact that there is no road traffic, and the geckos will keep young kids entertained for hours!brbrThroughout your visit, you and your companions will get to enjoy outstanding recreational facilities at Angler’s Reef. These community amenities include a heated swimming pool with outdoor bathrooms, chaise lounge chairs and tables overlooking the breathtaking blue waters of the Atlantic Ocean, and boat slips available for rent. Look forward to soaking up the sun at either of the 2 private beaches, located just a few short steps away from every home that flank the marina. Also the world famous Islamorada sandbar and Alligator Reef are a short boat ride from the opening of the channel.brbrbrPlease note, as of Aug 1, 2024. you will no longer be able to store a trailer outside the gate on the grass any longer. Trailers fitting under the carport are able to be stored there. Otherwise, we can recommend local storage lots you can contact.

108 Anglers Reef Islamorada 31' BOAT SLIP AVAILABLE

Islamorada, Florida, United States

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Bath