Vacation Rentals By Owner In Islamorada, FL

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

Bed

3

Bath

12

Sleeps

$1048.66

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

Bed

Bath

Sleeps

$478.34

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

$1494.8

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

Bed

Bath

Sleeps

$682.89

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

Bed

Bath

Sleeps

$349.85

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 559 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Islamorada, Florida, United States

Bed

Bath

Sleeps

$382.49

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 559 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Tropical Paradise Retreat in Islamorada! Pool, Pet-friendly, Free Parking!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$382.49

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 559 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Comfort and Convenience! Swimming Pool, Free Parking, Pets Allowed!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$782.75

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

Bed

Bath

Sleeps

$484.76

Windley Cottage is a private home in the exclusive gated community of Angler's Reef. This welcoming, tastefully-decorated home is located at mile marker 85, 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. ts central location is 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, 3paddle ball courts, bocce, tennis, a large playground, and basketball courts, an exercise course with 18 stations, and a multi-purpose path within the 40-acre park. Bring your rental agreement for free entry to the 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 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 or simply click on Book Now. 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.

ISLAMORADA PARADISE in ANGLERS REEF - Pool, Dock, Beach, Kayaks, Paddle Boards

Islamorada, Florida, United States

Bed

Bath

Sleeps

$382.49

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 559 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$758.25

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 559 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Best Place to Unwind! 2 Spacious Units, Free Breakfast, Swimming Pool!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$239.16

Discounted 3 to 6 months rentals. Plan your perfect getaways to paradise. 1/1 Fully Renovated Beautifully Designed Condo. Mm76 Sleeps 4. Boat dock equipped with water, electric & cleaning station as well as boat & trailer storage first come/ serve. 300k liability insurance required for boat. Private boat ramp also available. Enjoy all the community amenities pool, tennis court, pickle ball, shuffle board, corn hole, & life size tic tac toe. Building shares a washer & dryer. Bring home your Fresh Catch & prepare it in our fully equipped kitchen with all new appliances and a fully stocked for all your prep & cooking needs. We also provide a Weber gas grill. Condo is located on the 3rd floor. Minutes from the Famous Robbie’s and Anne’s Beach. Enjoy an array of restaurants , breweries, bars, shopping, fishing charters, dive & snorkel shops as well as weekly farmers markets. Islamorada full moon parties are always a great idea. Paradise Found

Condo

Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat

Islamorada, Florida, United States

Bed

Bath

Sleeps

$649.41

PROPERTY NAME: Little Bay Cottagebr82246 Overseas Highway, Islamorada, FloridabrbrLOCATION: Cottage located directly on the Florida BaybrbrMINIMUM STAY: Weekly or MonthlybrbrMILE MARKER: 82.2brbrDETAILS: br- Located on a one-acre lush tropical setting in a gated compound directly on Florida Baybr- One of 3 separate units for rent by the week or month, each sleeping up to 6 peoplebr- Protected dockage for up to a 34-foot boatbr- Sunning area with lounge chairs on the peninsulabr- Hammocks, pergola, and tiki for relaxingbr- Panoramic views of Florida Bay from the covered balconybr- Spacious interior with 2 bedrooms, 2 bathrooms, and a queen-size sleeper sofabr- Updated kitchen with new appliances and granite countertopsbrbrLittle Bay's Cottage is a ground-floor home with a unique floor plan. The main living area is in the center of the house, with a kitchen, dining area, sitting area, and full bathroom. To the right is a large bedroom with a king bed and full bathroom. The laundry area with a full-size washer and dryer is also located in this room. To the left of the living area is an enclosed sunroom that can be used as a second bedroom at night. The sofa in the sunroom converts to a queen-size sleeper, and there is also a twin-size Murphy bed. The cottage offers a little more privacy than the duplex units, but it does not have water views.brbrThe three units are available for rent by the week or month. Each unit sleeps up to 6 people, so you can rent one or all of them for a family reunion. Protected dockage in the little bay can accommodate boats up to 34 feet long. There is also a sunning area with lounge chairs on the peninsula, as well as hammocks, a pergola, and a tiki hut. All of the units have central air conditioning, a flat-screen TV in the living room, and WiFi. brbrSLEEPING ARRANGEMENTS: Sleeps 6 comfortablybrPrimary Bedroom: King Bed, Bathroom with Shower brGuest Bedroom: Queen Sleeper Sofa and Twin Murphy Bed, Bathroom with showerbrbrAMENITIES INCLUDE: Dockage for up to a 34 ft boat, Charcoal grill, Hammocks, Pergola, Swim and Snorkel in the bay. There is also Cable TV, WiFi, washer and dryer, air conditioning and free parking. brbrACTIVITIES: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures. Near by, there is John Pennekamp Coral Reef State Park, Theater of the Sea, Robbie's Marina and Islamorada Fishing Pier.brbrENHANCED CLEANING, DISINFECTION AND SANITIZATION: Our number one priority is the wellbeing and safety of our guests. We have contactless check-ins and check-outs. Our properties are cleaned and sanitized by professionally trained and equipped housekeepers who provide quality service, security and personal accountability. We use CDC housekeeping protocols, approved disinfectants and personal protection equipment. Our properties are private, well maintained, hygienic and sanitized. A whole safe and private space just for you and your family.

Cottage

Lush tropical plantings in a gated compound located directly on the Florida Bay

Islamorada, Florida, United States

Bed

2

Bath

Sleeps

$1197.33

Welcome to our beautiful Venetian Shores Canal Home—a luxurious waterfront retreat offering the ultimate Florida Keys experience! This spacious and elegantly furnished getaway features a private pool and spa, an outdoor kitchen, and everything you need for an unforgettable escape.brbrIncredible Amenities: Step inside, and you'll be welcomed by an open-concept living area that merges indoor and outdoor spaces seamlessly. With large windows framing canal views, the living room invites you to unwind in comfort. The fully-equipped gourmet kitchen is perfect for any cooking enthusiast, but the outdoor kitchen is where you'll want to be. Fire up the grill and dine alfresco on the expansive patio, surrounded by beautiful views.brbrPrivate Oasis: Outside, you'll find your own little paradise. The pool and spa on the back patio are ideal for a refreshing swim or a relaxing soak. Lounge poolside with a cold drink, soak up the sun, or unwind in the shade—tropical landscaping enhances the serene, secluded atmosphere, perfect for those vacation snapshots.brbrWaterfront Paradise: For boaters and water lovers, the canal-front location off Snake Creek is unbeatable. Enjoy quick access to the Florida Bay or Atlantic Ocean. With a private dock, you can bring your own boat or rent one nearby to explore the stunning waters of the Keys. Whether fishing, paddleboarding, or simply taking in the water views, this home is a haven for all things aquatic.brbrComfortable Bedrooms: The home's four tastefully decorated bedrooms provide a restful escape, each with comfortable bedding, canal views, en-suite bathrooms, and queen-sized beds for total comfort and privacy.brbrDiscover the Keys: Located in the coveted Venetian Shores neighborhood, you're close to local attractions like world-class fishing spots, the Theater of the Sea, and the unique shops and restaurants in Islamorada.brbrBook your stay at this Venetian Shores Canal Home with a pool, spa, and outdoor kitchen, and experience the best in luxury, comfort, and relaxation in the Florida Keys. Make lifelong memories with family and friends in this tropical retreat—your perfect Keys vacation awaits!

Casa Del Mar: A spacious 5-bedroom canal retreat in beautiful Islamorada.

Islamorada, Florida, United States

Bed

Bath

10

Sleeps

$719.96

Welcome to 104 Leoni Drive, a stunning new home in the highly sought-after Venetian Shores neighborhood of Islamorada. This 4-bedroom retreat has it all—a private pool, deepwater dockage, and a prime waterfront location with easy access to both the Ocean and Florida Bay.brbrStep inside, and you'll immediately feel at home. The open-concept living area is bright, airy, and beautifully designed, with high-end finishes and plenty of natural light. The gourmet kitchen has everything you need to whip up meals after a day on the water, and the spacious living room is perfect for unwinding in the evenings.brbrEach bedroom is thoughtfully designed for comfort, with plush bedding and stylish touches. The primary suite is a true retreat, featuring a private balcony with incredible waterfront views—the perfect spot for your morning coffee or an evening cocktail.brbrOutside, the pool invites you to soak up the Florida sun, while the private dock makes it easy to head out for a day of boating, fishing, or just relaxing by the water. With deepwater access via Snake Creek, you'll be on the ocean or bay in no time.brbrLocated in one of the best neighborhoods in Islamorada, you're just minutes from great restaurants, shopping, and all the fun the Keys have to offer. Whether you're here for adventure or just to kick back and relax, this home is the perfect place to do it all.brbrBook your stay today and experience the best of waterfront living in the Florida Keys! 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.

Luxury Waterfront Escape- Brand New Home In Venetian Shores

Islamorada, Florida, United States

Bed

3

Bath

8

Sleeps

$739.01

Recently updated Islamorada waterfront rental. Fully furnished and equipped kitchens! Come bring your boat or rent one to keep at the large private dock with cleaning station. brPlenty of parking to keep your trailer onsite as well as multiple other cars. This quiet community has direct access to the Gulf as well as the private beach area pictured.

Gulf access, private dock and private neighborhood beach!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1108.1

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Villa

Deactivated due to Bad Review and Low Productivity compared to other listings.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1462.5

Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 4 bedroom private oceanfront house overlooks the bay, with unparalleled privacy and nearly 2 acres of tropical trees, private boat docks and some of the best unobstructed sunset views the keys have to offer. Complete with fire pits, private outdoor seating, chaise lounges and plenty of room to unwind and relax.brbr*Guests can use all the amenities offered at La Jolla Resort including the pool and beach area.

4 Bedroom Private Oceanfront House - Bahia

Islamorada, Florida, United States

Bed