Vacation Home Rentals By Owner In Islamorada, FL

Located in the heart of Islamorada, our home sits on a private road with beach access. Enjoy 3 bedrooms with en-suite baths, chef's kitchen with Wolf and Subzero appliances, deck with dining table and seating, pool with tiki hut and tropical surroundings, even a putting green! Bike or walk to the best food and shops. This house is the perfect place to spend a month in paradise!brbrEnjoy secluded outdoor areas, great sunsets, excellent location by the best restaurants the keys has to offer and great quiet neighborhood of long term owners. Feel like a local here!

Turtle House Islamorada - 3 Bed/3 Bath Pool Home, Private Beach, Best Location

Islamorada, Florida, United States

Bed

Bath

7

Sleeps

$157.5

OCEAN VIEW, tiki covered rooftop deck, with concrete stairway.Escape to beautiful ocean views, sunrises / sunsets, in a charming refreshed, 1/1 house in Islamorada. brRelax in the cozy living room with a sofa perfect for unwinding after a day of exploring. brThe bedroom features a comfortable queen bed, ensuring a restful night's sleep. brEnjoy the convenience of a private bathroom with a refreshing shower. brFall in love with Islamorada, and enjoy the magic it has to offer. brNeighborhood walk on Jetty , surrounded by ocean on 3 sides, views of Islamorada sand bar, and Alligator Reef Lighthouse tower.brNeighborhood boat ramp to launch kayaks, paddleboards.brClose to waterfront restaurants & bars, live entertainment.brVery close to Founders Park, charter boating, can fish ocean, or gulf side waters.brbrSEASONAL RENTAL-brbrAvailable after 10/15/26. 20TH -30 NIGHT MINIMUM STAY @ $110.00 PER NIGHTbrLONG TERM RENTAL - 6 months to 12 month stay, $2,500.00 per monthbrHOA Approval required(minor background checks)

OCEANVIEW, ISLAMORADA - newly refreshed concrete conch cottage & tiki

Islamorada, Florida, United States

Bed

Bath

Sleeps

$2039.57

Peninsula Villa | Boat Dock | Heated Pool | Sunset Point

Islamorada, Florida, United States

Bed

Bath

Sleeps

$703.46

A 75' bulkhead on the main exit channel 3 houses from the bay.brPrivate boat slip in the neighborhood you can put your own boat with water accessbrPrivate access to the beach with picnic tables and dedicated swim area with no boat access to protect swimmers.brNearest boat ramp is 2 blocks down from the housebrbrLocated in the heart of Port Antigua, this canal front home boasts tropical vibes and can accommodate up to 6 guests to experience the “island life style.” Inside you will find an open living space permitting endless entertaining, a fully stocked kitchen with everything you need for home cooked meals, dining area for four, living room with an oversized sectional sofa, Smart TV with cable and wifi, laundry room with a full-size washer/dryer, three bedrooms (one king, two queens) and two full bathrooms.brbrStep outside to the large screened-in back porch and sip your morning coffee while watching the boats go by, or grill your catch of the day while the sun sets and lights up the sky in hues of orange, pink and purple. Biscayne Blvd is one of the few streets that backs up against our protected mangroves and provides extra privacy that other canal front homes can’t offer. The spacious downstairs area offers a covered outdoor space that can be used for dining, relaxing or escaping the Florida sun.brbrBring your boat, kayaks or enjoy the two paddle boards provided and take advantage of the 75’ of private dockage and 12,000 lb boat lift. Casa Del Pirata is only four houses in from the Florida Bay and just a short boat ride to Channel 5 bridge for easy oceanside access.brbrPort Antigua is a highly sought after community in Islamorada as it is known for its wide canals, boat ramp, and infamous bay front white sandy beach with tiki huts and picnic tables. These are private amenities and are only accessible by Port Antigua homeowners and guests.brbrThis home is located on the island of Lower Matecumbe Key. Just 5 minutes north is the world famous Robbies, which offers fishing and snorkel charters, a restaurant and bar, shops, parasailing, kayaks and paddle board rentals. You can even hand feed the enormous tarpon! Habanos is another local favorite, where you can experience oceanfront dining and classic Cuban cuisine. Downtown Islamorada is only 10 minutes north and offers endless restaurants, breweries, shopping, activities and grocery store. Key West is a beautiful 1.5 hour drive south.

Cozy canal in the Keys - leads directly into crystal blue ocean!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$779.9

Forget your worries in this private water front home.brbrThis private two family home is ideal of large fishing groups and multi-generational families who want separate living spaces. Four total bedrooms, two upstairs and two downstairs with bunk beds on both floors offers optimal space for larger groups. brbrHome offers a large 40 foot ocean side canal space with boat lift (max boat weight at 15,000 lbs) you can park your boat. We have an outdoor bait freezer, ice machine, and cut station. Everything you need for the seasoned fishermen and fisherwomen. If you need a boat charter, look no further, we offer that too! We will pick you up at the home with our beautiful charter boat. bigdavechartersandtours.combrbrThe home has a private pool with at tiki hut that has a smart TV you can enjoy your favorite programs while observing wildlife in the canal. We have frequent manatee and dolphin sightings! brbrThe home has two full kitchens and grill and a cut station you can make full use of after a long day of fishing. brbrThe home offers a large driveway that can fit up to four cars or three cars and a boat trailer. brbrWe are 2 hours from Key West and 1 hour from Miami. It is a premiere spot regardless of what your trip goals are, there is something for everyone. brbrBook our website fishing & excursions bigdavechartersandtours.com

Waterfront home in the heart of the fishing capital of the world.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1719.9

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

Islamorada, Florida, United States

Bed

Bath

Sleeps

$466.47

Welcome to Islamorada, the fishing capital of the world!brbrOVERVIEWbrThis NEWLY FURNISHED home offers DIRECT ACCESS to the Atlantic and is nestled in the middle of Anglers Reef, a top-of-the-line tropical paradise getaway located within minutes of many amazing attractions in the area that are sure to keep you busy. Whether your vacation includes sightseeing, ecological tours, locally produced artisan crafts, hand-feeding giant tarpon, swimming through breathtaking coral reefs, hanging out at the sandbar, relaxing by the water as you watch the sun rays glitter across the water, listening to live music within walking distance, or fishing in the most pristine water Florida has to offer. The Kay K IV out of Whale Harbor Marina offers the highest quality fishing charters in the area. This home's location offers anyone a top-notch, luxurious, affordable, and unforgettable trip to the Florida Keys.brbrBEDROOMSbrShowcasing a spacious master bedroom with a vibrant en suite bathroom with a walk-in shower and an overlooking balcony. The other bedroom offers a large accommodation for sleeping arrangements with a queen and 2 full-sized beds, as well as its own private full bathroom and balcony.brbrLAUNDRYbrNEW large washer and dryerbrbrDOWNSTAIRSbrFeaturing a half-bath and an open floor plan, which facilitates amazing conversations and laughs between the living room, dining room, and kitchen.brbrLIVING ROOMbrNewly furnished with a large, amazingly comfortable family-sized couch and 65-inch ROKU TV are sure to provide amazing entertainment.brbrDINING AREAbrBoasting an intricate root wooden table with 4 chairs and 3 bar stools, Capable of including everyone for big hearty meals. brbrKITCHENbrIncluding bar seating, a dishwasher, sink, full oven and stovetop, microwave, coffeemaker, refrigerator, and other appliances and kitchenware, this roomy kitchen provides enough counter area to prepare any meal you want. brbrBACK PATIObrFurnished with seating to enjoy meals and relax outside in the tropical breeze.brbrCOVERED CAR PORTbrlocated just outside the back door.brbrPRIVATE BEACHbrLocated on either side of the community and offers amazing views of the Atlantic Ocean. Includes patio seating, as well as paddleboards and kayaks for adventurous journeys. brbrLUXURY RESORT POOLbrLocated at the center of the community and overlooks the Atlantic Ocean. It contains chairs, recliners, and a bathroom.brbrBOAT DOCKbrAvailable to any guest for a personal watercraft at an extra cost. Electric and fresh water are included. The vessel size cannot exceed 31 feet overall. Islamarina at Snake Creek offers boat gas and fishing supplies within 1 mile of home.brbrOUR STORYbrOur family has personally vacationed at this community for 18+ years and has yet to find another area as beautiful and incorporated as this one. The close proximity to anything anyone could want from the Florida Keys is unmatched. This is what led us to purchase this cozy home and share it with others to experience this master-class vacation spot in the Florida Keys.

Angler's Reef : Waterfront Beach, Pool, Kayaks & Boat Dock Available

Islamorada, Florida, United States

Bed

Bath

Sleeps

$529.11

Short Descriptionbrbr Amenities: Free Boat dockage, htd pool, BBQ grill, EV chargerbr Game room br Mins to the famous Islamorada Sandbar by paddle, boat, or kayak!br ️ Comfortable bedrooms with premium amenitiesbr Dog friendly br 24/7 guest support team for a seamless staybrbrThe SpacebrExperience relaxed island living at At the Sandbar, a modern coastal vacation rental located in the private oceanfront Peaceful Palms community in Islamorada. This waterfront townhome is ideal for families, couples, and boating enthusiasts seeking a peaceful Florida Keys getaway with upscale comfort and convenience.brGuests enjoy dock access, oceanfront community amenities, and scenic water views throughout the property. While there is no beach or direct shoreline access, the location is perfect for boating, paddleboarding, fishing, and soaking in the laid-back Keys lifestyle away from crowded tourist areas.brJust minutes from Islamorada's best restaurants, waterfront bars, parks, marinas, and local shops — and a short paddleboard or boat ride to the famous Islamorada Sandbar. This coastal retreat offers the perfect balance of privacy, location, and true Florida Keys charm.brbrWhen you arrive, you'll find a private garage with space for one vehicle (There is a parking spot in front of the villa for an additional vehicle), an EV charger, and an array of AMENITIES YOU WILL LOVE, including: a BBQ grill, two adult bikes, two kid bikes, and two paddleboards. Beyond the garage, the game room awaits, featuring a ping-pong table, life-size Connect Four, wall darts, workout equipment, TV, cozy sofa, board games, and a mini fridge—perfect for hours of entertainment.brbrOn the second floor, the open-concept layout seamlessly connects the kitchen, dining, and living spaces. The kitchen boasts top-of-the-line appliances and a peninsula with seating for six that's ideal for casual dining or morning coffee. The living room is outfitted with two comfortable sofas, a smart TV, and access to a covered balcony. The balcony features two dining areas with picturesque views of the dock, making it an excellent spot for alfresco meals or evening cocktails.brbrFor your convenience, a washer and dryer are located on the third-floor hallway.brbr♛The Primary Suite (3rd floor) provides a generously sized retreat, with calm accents, balcony with water views, king size bed, premium bedding, and a luxe primary ensuite bathroom. A frameless shower and double vanity sink offer the comforts of home.brbr ️ All bedrooms feature the following amenities:brbr✔ Premium beds, pillows, linens, and sheetsbr✔ Smart TVsbr✔ Ample closet spacesbrbrBedroom 1 (Second Floor): Queen-sized bed brBedroom 2 (Third Floor): Queen-sized bed & a twin trundle bedbrPrimary Bedroom 3 (Third Floor): King-sized bedbrbr All full Bathrooms are generously stocked with:brbr✔ Shampoo & conditionerbr✔ Body soapbr✔ Fluffy towelsbr✔ Toilet tissue brbrBathroom 1 (Second Floor): Frameless shower, sink, and toiletbrBathroom 2 (Third Floor): Ensuite, frameless shower, sink, and toiletbrPrimary Bathroom 3 (Third Floor): Ensuite, frameless shower, double vanity sink, and toilet brbr Outdoor ParadisebrRelax and unwind with top-tier amenities, including an oceanside boat dock, private community heated swimming pool, and walking proximity to the best and most popular restaurants, shops, incredible wildlife and fishing attractions. The pool area features lounge furniture, bathrooms, and is heated for swimming year-round. Watch our beautiful sunrises from the comfort of the community's oceanside dock.brbrCommon AreasbrHeated pool + lounge chairsbrRestroomsbrBoat dockbrbrBoat Dockage Information: *Dockage is included with rental reservationbr-Complimentary boat dockage (subject to availability) -Dockage is limited and based on availability. *We recommend reserving dockage upon booking.br-We can accommodate boats up to 24' .br- Contact us to confirm if the dock can accommodate your boat.br-Guest(s) are required to complete a boat dockage agreement form (BDA), to reserve boat dockage.br-There is no trailer storage or boat ramp available on-site. Our recommendations for both will be sent along with our boat dockage agreement form.brbr Neighborhood OverviewbrBeing located in the heart of Islamorada makes our property accessible to walk to over 10 restaurants, paddle board and kayak the islands, snorkel the reefs and experience the ultimate Keys Life Vacation. There are great bike, running & walking paths in Islamorada….fun for the entire family! brbrKayaks can be delivered for a cost directly to your villa for use during your stay. Islamorada is a serene paradise in the Florida Keys that embodies the essence of island living. With easy access to world-class fishing, diving, and watersports, Islamorada is the ideal destination to experience the natural beauty and laid-back lifestyle of the Keys.brbr Points of Interest: brbr- Famous Islamorada Sandbar is minutes away via boat, kayak, or paddle board!br- Islamorada Library Beach Park (7 min): Water access on a mangrove channel with amazing play equipment, shaded tables & BBQ facilities. br- Morada Way Arts & Cultural District (7 min): Stroll through art galleries, boutique shops, and enjoy local cuisine at the weekly art walk eventbr- Theater of the Sea (4 min): Enjoy interactive marine shows and swim with dolphins in this unique marine park.br- Robbie's Marina (12 min): Feed the tarpon, dine at waterfront restaurants, and shop for souvenirs at this bustling marina.br- History of Diving Museum (5 min): Explore the fascinating history of scuba diving through exhibits and artifacts.br- Anne's Beach (15 min): Relax on the sandy shores or take a leisurely swim in the calm waters of this picturesque beach.brbrHouse RulesbrbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrbr**All guests must sign our rental agreement as mandated by Florida Law.**brbr-The minimum rental age is 25. A picture ID must be provided to the company no less than 72 hours (about 3 days) before arrival.br-An accurate guest count must be provided.br-No smoking or vaping. If evidence is discovered of either smoking or vaping, the guest will be subject to a fine of up to $1,000br-No parties or events. If unauthorized persons are discovered on the premises, guests will be subject to additional fees and/or immediate eviction.br-Quiet time is from 10:00 PM to 8:00 AM. brbrStarter Supplies:brWe provide trash bags, paper towels, toilet paper, detergent, and bathroom amenities to accommodate this home's maximum occupancy for the first three days of your stay.brbrSame-Day Bookings: brSame-day bookings require approval from the company. We will ask you to provide information on your group and the purpose of your stay. If your stay is approved, we require a government-issued ID for identity verification. Your phone number must match the phone number on your account, or we will not be able to honor your reservation. Same-day reservations will not be accepted after 2:00 PM. All same-day reservations require at least 3 hours before check-in. We may have to extend check-in time to later than 4:00 PM.brbrPet Policy:brThis property is dog-friendly with an additional fee of $295, per pet. While staying with us, you are responsible for the actions of your pet. Please keep your dog(s) off the furniture and pick up all waste. All waste should be bagged and disposed of in the outside trash bin. Failure to comply with our pet policy will result in an additional $100 fee. Please let us know if you will be bringing your dog (only dogs are permitted). brbrRelease of Liability for Recreational EquipmentbrGuests agree to use paddleboards and bikes at their own risk. The property management and owners are not liable for any injuries, damages, or losses related to their use. By using these items, guests release the property management and owners from all claims and liabilities. brbrMid-Stay Cleaning Requirement:brFor all extended stays of 30 nights or longer, a mandatory mid-stay cleaning is required every 30 days.brIf your reservation is 60 days, two mid-stay cleanings will be required, and so on.brThis helps keep the home maintained during longer stays and ensures everything stays in great condition.brMid-Stay Cleaning Fee: $285brWe'll reach out after booking to schedule the mid-stay cleaning(s) and send the payment link.

At The Sandbar: Partial Ocean View, Htd Pool, Free Dockage, GameRoom, EV Charger

Islamorada, Florida, United States

Bed

Bath

Sleeps

$385.02

3/2 Waterfront Home in Lower Matecumbe Key in Islamorada, Florida. Featuring a 70' ft private dock with 2 boatlifts (1- 10,000 lbs capacity, 1- 20,000 lb capacity)- both available for rental separately. Home is minutes away from most attractions. brThis beautiful home accommodates up to eight people and is completely decorated.brbrMaster Bedroom has a King-size bed with a flat panel LCD Television. Southern facing window lets in plenty of natural light. Bedroom features a master bath and a walk in closet with ample room for storage.brbrBathroom #2 has a queen sized bed and a private televisionbrbrBathroom #3 has two full size bunk beds and a private television. brbrOne full sized bathroom in addition to master bath is conveniently located by bedrooms.brbrThe living room has an entertainment center with a flat panel LCD Television. Lovely Kitchen /dining area featuring a table for 8. brbrUpstairs balcony extends width of property and contains a BBQ and seating area. brbrDownstairs storage room has a half bath, full size washer & dryer, Ice Machine, Refrigerator, Freezer and plenty of space for Fishing equipment/rod storage. brbrProperty downstairs has an outdoor shower, a fish cleaning station and 2 elevator boat lifts (10k lbs & 20k lbs) available for rental separately. Owner must approve boat lift rental before booking the property if you plan to bring your boat.

Tarpon Bend ocean view with boat lifts

Islamorada, Florida, United States

Bed

Bath

Sleeps

$785.52

Happy Tarpon - A special place for you in the beautiful Florida Keys. Enjoy our recently renovated home in the heart of Islamorada. Furnished for easy tropical living. You can swim in the heated pool after a day on the water Boating, Fishing, lobstering, Sailboarding, Skindiving or Canoeing. Islamorada has it all. Your boat is next to the house in the deep-water boat dock. The dock holds up to a 28' foot boat in the protected canal. You will have direct access to the Back country and world-class flats fishing. It is a short run to the Ocean for world-class deep sea fishing. There is also a fish cleaning station next to the dock with fresh water. brbrThe center-piece of our home is the heated private Pool directly outside the living room and kitchen. Fishermen, kayakers, paddle boarders and canoe enthusiasts alike return year after year. You will love Happy Tarpon. Definitely a great place to relax and enjoy between fishing or scuba or catching lobsters or even sightseeing. !!br brHappy Tarpon has 3 bedrooms and 3 1/2 baths. A full-size laundry. And a fully equipted kitchen. brThe marble floors, comfortable beds and tropical furniture make this home delightful easy living.brHappy Tarpon is centrally located to all that Islamorada has to offer: Walk 1/2 a block to the Lorelei Restaurant and Marina or to other nearby restaurants and activities. We have excellent shopping, dining, fishing, boating and scuba diving in the Florida Keys. brCONTACT OWNER FOR MORE INFORMATIONbrIslamorada, Village of Islands Rental License #26-0321brbrKeywords: Single-family home, Private Heated Pool, Private Boat Dock, Sunset views. On Florida Bay. Beautifully renovated two-story Islamorada house, free Wifi, cable TVs, Easy Access to Back Country Fishing and Ocean Fishing. Peaceful. Private Home. Manatee watching for the docks. Scuba Diving. Kayaking. Paddle Boarding. Snorkeling. Manatees. Fly Fishing. Off-shore fishing. Swimming. Sunbathing. Shopping. Guided Fishing. Bird Watching. Eco tourism. Wildlife viewing. Para sailing. Pier fishing. Wind surfing.

Enjoy Happy Tarpon: Boat Dock - Private Pool - Islamorada Sunsets & Family Fun!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$2531.12

Kara Pan - Islamorada's Premier Oceanfront Estate Home... Kara Pan 1. Discreet Key West style home is situated on a four-acre parcel surrounded by lush landscaping and a natural white sand beach dotted with palm trees. When entering the winding driveway, you will be intrigued with anticipation of the captivating views that are only seconds away. Kara Pan is comprised of five en-suites each with its own personality. Every bedroom suite has French doors that invite you out to the expansive wrap around balcony and gorgeous ocean views. The open concept kitchen, dining room and living room offers families the comfort of dining together. Kara Pan also offers their Carriage House which has one bedroom, one bath, living room and kitchen if you need a little extra space. Enjoy the privacy of your own heated swimming pool, hot tub, tennis and basketball courts. You are in walking distance to many of Islamorada's boutiques, cafes, shops and galleries. The Art Walk is located minutes away within walking distance and is scheduled every third Thursday. Weekly rental rate: $14,500 and monthly rental rates available upon request. The Carriage House is $1000 added to the rate. brVACATION RENTAL LICENSE: 24-0293brIf 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.

Experience luxury in this 5-bedroom oceanfront home in Islamorada, perfect for 12 guests.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$2035.35

Exquisite Oceanfront - Luxury and tranquility await you at this elegant Islamorada oceanfront estate. Drive through a gated entry to your own paradise. The entire property offers spectacular views of the Florida Keys waters and boasts 150 feet of luxurious beachfront living. The main house offers four bedrooms and four bathrooms with a powder room adjacent to the living area. Two king ensuites are located on the main level along with a twin bedroom and shared pool bathroom. The upstairs is dedicated to your own master suite with spa bathroom and cozy living area. French doors open to your private oceanfront veranda to catch the morning sunrise and ocean breezes. Separate one bedroom, one bath guest home. Relax in the infinity edge pool and spa while cooking lunch or dinner at the outdoor grill and bar. Two kayaks, bikes and beach toys are included with the property. VACATION RENTAL LICENSE: 24-0325brIf 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.

Discover luxury in this 5-bedroom exquisite oceanfront pool home in beautiful Islamorada.

Islamorada, Florida, United States

5

Bed

5

Bath

10

Sleeps

$241.01

PROPERTY NAME: Fisherman's Gembr113 Iroquois Drive Islamorada, FloridabrbrLOCATION: Oceanside Canal home with Boat dock and Boat RampbrbrMIMINUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedbrbrMILE MARKER: 74brbr This waterfront, ground-level Islamorada home, featuring lavish amenities and gorgeous views, is destined to be the highlight of your next coastal escape. A lush outdoor space invites you to unwind on the dock, grill up the catch of the day, and grab a kayak for a sunset rowing session. Conveniently located, you'll find Robbie's of Islamorada, Long Key State Park, and the Theater of the Sea, all within an 11-mile radius. Spend a day feeding the famous tarpons, exploring the natural beauty of the Florida Keys, and interacting with exotic marine life. Windley Key Fossil Reef Geological State Park, close by, offers unique geological formations and fossilized coral for nature enthusiasts. Long-term boat rentals are available nearby if you prefer sport fishing, snorkeling, or scuba-diving.brbrStep into this delightful hideaway and be welcomed by sunlit, open-concept living areas bursting with colorful coastal decor. Lounge on the plush sofa to stream your favorite shows on the smart TV, or enjoy your morning coffee on the well-furnished patio as the boats float by. A well-appointed kitchen boasts modern appliances, ample counter space, and everything you need to craft a delicious home-cooked meal. With ultra-high-speed internet perfect for gaming or business activities, this rental is ideal for any work-from-home professionals hoping to get a little work done vacation-style.brbrFollowing a day of fun in the sun, sway in the hammock and let the sound of the waves serenade you to sleep in paradise.

Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property

Islamorada, Florida, United States

Bed

Bath

Sleeps

$515.1

Village of Islamorada license #24-0370br138 Anglers Way and boat slip #1 for 26' max boat length for this slip (extra fee)brCall me for more information 305-240-0592br2 large bedrooms amd 2.5 bathrooms. largest floorplan of two bedroom in Anglers.br Community kayaks and paddleboards are avail to use (just have to sign a waiver)brThis large Oceanfront Villa has 2 bedrooms (one with king bed and the other with One QUEEN SIZE BED and twin bunk beds) and 2 full bathrooms located on the 2nd floor, both with private balcony's. Down stairs there is a half bath, a full kitchen with stainless steel appliances, granite counters, living/dining room, wood floors, cable TV, Wi-Fi and 2 open porches with seating.This oceanfront resort is a boutique complex of 52 homes inspired by Key West architecture that was built in 2007. Gate community, located off the Old Hwy at MM 86 in Islamorada. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home’s boat slip is available for rent with a deep channel out to the Atlantic. Be at Alligator Light house or the Famous Islamorada (Holiday Isle) sandbar in minutes. Launch your kayak or paddle board from the private beachbrbrKayaks are now available to all homes (provided by the community) on a first come, first serve basis. A waiver needs to be signed (attached to welcome email) in order to be able to use them.brbrPlease 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.brbrCome on down and put your toes in the sand. It's always better in the Florida Keys.Angler’s Reef is the perfect place for all fishing and diving enthusiasts. Islamorada is known as “The Sport fishing Capital of the World”. Water activities abound including: diving, snorkeling, Para sailing, kiteboarding, paddle boarding, kayaking, and more. You may even spot manatees at the Dock. Fine dining and unique shops are within walking distance: Island Grill (Famous for their tuna nachos) serving breakfast, lunch and dinner oceanfront with live music. For late night entertainment, walk on over to Hog Heaven for a fun night of dancing. Also, within in walking distance is Theatre of the Sea, where you can watch a live dolphin show or even swim with the dolphins!brbrBring your boat (up to 26') max. If you have a larger boat, I will need to put it in another slip and there is an additional fee.

Islamorada-Anglers Reef-LARGE/updated/Views DOCKAGE AVAILABLE

Islamorada, Florida, United States

Bed

Bath

Sleeps

$723.07

Islamorada Vacation Rental LICENSE #: 26-1243brbrSpacious five bedroom home on huge canal. Tons of dockage, bait freezer, and fish cleaning station!! SUPER PRIVATE!!! brbrAmazing waterfront restaurants close by!!! Boat rental and paddle board/kayak company that will deliver boat to dock for your stay. brbrDream home in they keys is a 4000 square foot home on water with heated/chilled Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. It has 5 large bedrooms and three baths. Equipped with four king beds, one queen bed, one queen sofa sleeper, a futon and four singles. All top quality mattresses. All down beddering and sheets 800 or higher. Both the down stairs and up stairs have tv and dvd. Three of the bedrooms have TV's. The kitchen is extremely spacious and well-equipped. brThe screened verandah overlooks the pool and water area filled with blooming tropical landscaping. The veranda has two seating areas and a large teak table that can extend to 10 feet and seat 12 comfortably. Just a sliding glass door from the kitchen. Windows and sliding glass doors make up most of the house providing the feeling of living at one with the tropics. brbrThe outdoor entertainment area is complete with heated pool, barbecue grill and 100 foot of dock space on deep natural, crystal clear canal which is right at channel two.brBeautiful Tiki Hut to enjoy our wonderful weather.brbrMy cancellation policy is I ask for a booking deposit (VRBO takes THEIR fee) at this time, I then as for the balance 60 days prior to your stay. As long as I can rebook your dates I refund 100%. VRBO also refunds their service fee when I refund 100%. VRBO does not give me this option on their site. I send you a contract when you book, detailing this. brKeywords: House

Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access

Islamorada, Florida, United States

5

Bed

Bath

12

Sleeps

$793.13

Located in the sweet spot of the Florida Keys - Islamorada. Custom built and designed by an Award winning architect in 2019. Wonderful floor to ceiling glass captures amazing ocean views. Warm reclaimed teak flooring. Fabulous ocean front views, 4 outdoor ocean view patios plus 1 small outdoor Master bath deck. Chef appointed kitchen with Wolf stove and Subzero fridge. Wolf wine cooler and warming oven. Ocean front Master bedroom has its own private balcony and bathroom suite. Guest bedroom has ocean front views and private bath. Other guest bedroom has queen bed and private bath. brbrVanishing edge pool on all sides and spa. Pool & spa heat, bubble jets and lights are controlled from your iPhone. 50 foot of beachfront property, great for paddle boarding, kayaking, kiteboarding and snorkeling. Bicycles and paddle boards included. Great loft space with lots of natural light from clerestory glass. 3,050 ft.² of livable space on three levels.brbrIncluded is a 23 foot Contender boat docked next door at our resort property for guest use. Boating experience is required.brbr

Ocean Front Contemporary Beach House, Islamorada.

Islamorada, Florida, United States

4

Bed

Bath

6

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

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Bath

Sleeps

$1534.63

TED’S PLACEbrbrLicense # VR052 - Minimum Stay 1 Week, Saturday thru Saturday – Unbeatable Location - 1.5 acres – Bayfront – Gated & Secluded – Walking Distance to Lorelei and other great spots - 5/4 Home with Heated Infinity Pool and Hot Tub – Protected Dockage for Boats up to 30’ – Easy safe and secure parking for your boat trailer - Stunning Views – Great Amenities inc. Paddleboards, Kayaks, Gym, Outdoor Grill Station & Bar, Sunset Cabana, Smart TV’s, Indoor & Outdoor Sonos Sound System, Pool Table, Ping Pong, Shuffleboard, Cornhole, Firepit.brbrDesigned to be the ultimate vacation home for couples, families with teenage children or groups of fishing friends. brbrPlease note that Ted's Place has multiple deep water features within close proximity of the house. brbrbrTHE LOCATIONbrbrTed’s Place – the spectacular former estate of Ted Williams is superbly situated at Mile Marker 82 in the heart of fabulous Islamorada – the Village of Islands, the Sportfishing Capital of the World and recently described by the Miami Herald as ‘the Cool Key’.brbrIts central location on Upper Matecumbe Key means easy access to the best that Islamorada has to offer. A short stroll to the end of the street takes you to the Islamorada Fishing Club or the Lorelei Restaurant and Cabana Bar – popular hangouts for locals and visitors alike. Explore further afield and you will find many of the area’s top-rated marina’s, restaurants, craft breweries, tiki bars, art galleries and boutiques.brbrSet well away from the busy Overseas Highway, this gated estate fronts directly on to glorious Florida Bay for breathtaking sunsets and panoramic views of shimmering, teal waters, mangrove islands and the turquoise horizon.brbrIslamorada is uniquely positioned at the confluence of the Atlantic, the Gulf of Mexico and the Everglades National Park. For fishing friends and families this is a seriously fishy venue. The world record producing bonefish flats of Shell Key are seconds away from the dock, a few minutes further takes one to the tarpon hotspots of Florida Bay or the Oceanside flats. The fertile fishing grounds of the Gulfstream are easily accessed via nearby Whale Harbor Channel. Opportunities for lobstering, snorkeling, kayaking, paddle boarding and nature watching abound right outside your door. brbrWhen Baseball legend Ted Williams moved to the Keys in the fifties, he had the pick of the best waterfront locations to call home. He chose here. After spending a week treading in his footsteps, you will understand why. brbrTHE ESTATEbrbrSpanning 1.5 acres and accessed via an electric gate on quiet Madeira Road, Ted’s Place is truly a tropical paradise. A long, winding driveway leads you through expansive, mature gardens populated with hundreds of native trees, shrubs and flowering plants, all designed to attract an abundance of butterflies and birdlife. Towering, swaying palms surround the main home, rambling Bourgainvillea provide vibrant splashes of color and comical curly-tailed lizards stand sentry on the stone garden walls.brbrAccessing the bayside of the estate you are immediately struck by the infinity-edged swimming pool and spa and an assortment of patio’s, decks, outdoor dining areas and a bar area - all laid out to maximize the spectacular open water views.brbrA small mangrove island protects the sea wall and dockage creating a shallow lagoon that shields boats from excessive wind and waves. It’s also an ideal place to kayak and paddle board on windy days. Most days an Osprey perches on the largest palm, surveying the lagoon for its preferred prey of Mullet. Schools of large Snapper and Parrotfish hang out in the shade of the floating dock and families of Manatee’s visit on a frequent basis. If you are lucky you may witness dolphins playing beyond the island in the deeper waters of the Bay.brbrIf you are not transfixed by the natural beauty of it all, there are many further outdoor features to occupy your time – a small gym located in the garden room, a pool table, darts board and ring toss in the bar area, shuffleboard on the porch, ping pong in the entryway, corn hole in the yard and a fire pit for toasting marshmallows on cooler winter evenings.brbrIf you are tired of the Ted’s Place you are tired of life. Kick back, relax and enjoy this serene oasis.brbrTHE HISTORIC HOMEbrbrTed Williams was the quintessential all-American hero. His achievements as a baseball hitter for the Boston Red Sox remain unsurpassed to this day. In between setting all time batting records he served his country with distinction as a fearless fighter pilot during World War II. Upon his retirement from baseball he headed south to Islamorada where he quickly distinguished himself as one of the best fisherman the Keys had ever seen. The media attention Williams brought with him truly put Islamorada on the map as one of the leading sportfishing destinations in the world.brbrTed Williams evidently loved the Keys and its people. The fact that he lived in this house for forty years makes Ted’s Place one of the most historically significant homes in the Upper Keys.brbrToday, the original concrete shell of Williams house still forms the superstructure. But beyond that, subsequent owners have upgraded the interior and exterior to create 5,400 sq/ft of living space (3,600 sq/ft interior and 1800 sq/ft of porches, balconies and terraces) laid out and equipped for contemporary lifestyles, but careful to preserve the Old Florida charm. The ground floor of the home offers an open plan living design and features a well equipped kitchen by the modern masters, Bulthaup and a dining area furnished in the minimalist mid-century modern style with superb views towards the water. Large sliding glass doors bring the outdoors in to the living areas and provide plenty of natural light. One en-suite bedroom makes up the ground floor.brbrUpstairs, there are a further four bedrooms and three bathrooms. The master suite is as large as some condominiums in the Keys and opens on to a large balcony overlooking Florida Bay. All bathrooms are equipped with the best power showers and porcelain from Hans Grohe and Duravit. Large Smart TV’s are situated in the living room and master bedroom and Wi-fi is available throughout the home. Please note the 5th bedroom has two twin beds - the other 4 bedrooms have King beds..brbrThe owner of this home is an avid saltwater fly fisherman and this is reflected in the fine artwork by notable marine artists such as Al Barnes, Tim Borski, Jorge Martinez and Roge Fowler that adorns many wall spaces.brbrTo stay at Ted’s Place is to immerse oneself in the natural beauty of the Florida Keys whilst still enjoying the creature comforts one would expect from modern living. You may find you never want or need to leave the Estate except perhaps by boat – any of the many great fishing guides in the area will be happy to pick you up by skiff or bay boat right at the dock.

Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.

Islamorada, Florida, United States

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Bath

Sleeps

$1102.08

Heart of Morada - This unique townhome is located bay front at Mile Marker 81.5 on U.S. Highway 1 in the heart of downtown Islamorada. Just beyond the discreet gates, an easy walk or bike ride away, is all that this Florida Keys village has to offer boutiques, galleries, dining, spa relaxation, beaches and the ultimate saltwater fishing experiences. Kayak, paddleboard or boat for a day of flats fishing right from your backyard. Or simply enjoy home in lush tropical surroundings at your private 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. brVR-24-2069 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.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.

Experience luxury at Heart of Morada, a 3-bedroom condo in beautiful Islamorada.

Islamorada, Florida, United States

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