Vacation Home Rentals By Owner In Islamorada, FL

PRIVATE BEACH / Pickleball Court and Tiki Bar / Heated Pool / Designated Paradise Key

Islamorada, Florida, United States

Bed

Bath

Sleeps

$653.49

Paradise is only a click away. Our 2 BR/2.5 BA conch style townhouse is available for weekly and monthly vacation rentals. Our unit has unobstructed direct ocean views, and overlooks the resort style swimming pool. Dock space is available to rent as well for boats up to 31 ft. brThis home is great for a family vacation. There is also a beach and kayaks available. Lush, tropical landscape adorns this property.

Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$371.32

brbrWelcome to our home away from home. White Marlin Beach, Waterfront property, quick access to the Bay from our canal. The best part is that you have access to our community private beach. You can kayak, swim, snorkel, fish, sun bathe and enjoy our beautiful Sunsets right from our beach. There are many things to do and many restaurant's to choose from. brEnjoy a peaceful stay at this lovely 2-bedroom house in Islamorada. This quaint property offers a cozy atmosphere that will make guests feel right at home. The bedrooms feature a comfortable king bed and a queen bed, ensuring a restful night's sleep. The bathroom is equipped with a hair dryer and a refreshing shower. In the additional living room space, there is a sofa bed for extra convenience. Stay connected with WiFi and take advantage of the washing machine and dryer to keep your clothes fresh. With AC throughout the house, you'll stay cool even on warm days. We look forward to hosting you at our place. You will definitely relax and make memories to last a lifetime.

Charming 2-bedroom house in enchanting Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$424.61

WATER FRONT CANAL HOME 3 BEDROOM/ 3 BATH HOME. brBRING YOUR BOAT, LOTS OF PROTECTED DOCKAGE. FULLY UPDATED HOME. HIGH SPEED WiFi and ALL SMART TVs. Coconut trees provide the shade to enjoy the calm breeze as you sit in one of our comfortable adirondack chairs and enjoy the tranquility.brUpdated Wi-Fi with new easy to connect AT&T modem. brDOCK RIGHT AT THE HOUSE! FISHING FUN RIGHT OFF DOCK!brGUEST BATHROOMS RENOVATED AND UPDATED! NICE PROTECTED DOCKAGE.brLOTS TO SEE AND DO CLOSE BY! MANY RESTAURANTS CLOSE BY!brWE MAKE COMMUNICATION EASY AND ALWAYS PROMPTLY RESPOND TO OUR GUESTS.brCLEANLINESS IS MORE IMPORTANT THAN EVER!brHOME IS CLEAN AND FRESH! INTERIOR RECENTLY PAINTED! brBRING YOUR OWN BOAT OR RENT ONE LOCALLY.brbrWEEKLY STAYS ARE WELCOME. LICENSE #VR-113. brbrCharming cozy private waterfront house on Atlantic side canal. brGreat protected dockage and room for your trailer. Newly paved, private road.brbrNew kitchen with all wood cabinets, granite counter tops and stainless appliances. The kitchen is fully equiped with all the essentials.brbrThree bedrooms and three bathrooms. Downstairs bedroom has full bathroom with shower and is separate from upstairs and opens to carport. Home is perfect for four adult plus two kids.brbrWe have lots of great dockage for your boat. The large dock/seawall area extends 90 feet and includes a nice cut-in slip. The dock includes electric, water. There is also a cleaning station on the dock. Also there is plenty of room for trailers on the side of the home. It's all about the boating. brbrThere are several local boat ramp options close by. brbrKeep in mind that trip insurance is available and is recommended.brThere are many options including through VRBO or other mainstream recognizable third party providers.brBe sure to understand the coverage, benefits and limitation of any policy you purchase.brbrbrINSPECTED, PERMITTED & LICENSED BY THE VILLIAGE OF ISLAMORADA # VR-113.brbrKeywords: License #VR-113, Islamorada Florida, Lower Matecumbe, Dockage, Waterfront, WiFi, Internet, clean, Tropical, Home, waterfront, deep dockage, bungalow, shopping, dinning, beach, kayak, scuba, snorkeling, lobsterbrfishing, dock, boat, ocean, bay, Keys, key, Islamorada, Upper Keys, Lower Matecumbe, kitchen, open, clean, bright, comfortable, private, protected, deep water, boating, swimming,! Amazing

CHARMING WATERFRONT OCEANSIDE CANAL HOME-LARGE PROTECTED DOCKAGE-WiFi-SMART TVs.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1884.12

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, tiki hut on private beach, heated pool and wireless remote Internet. Southern Diversion pool and patio area has just been completely renovated with marble decks.brbrIslamorada is located one hour and 1/2 south of South Beach and two hours north of Key West. This spectacular oceanfront estate features 5 bedrooms, 3.5 baths. Bedroom One: king bed, Bedroom Two: 1King bed , Bedroom Three: 1 King bed, Bedroom Four: 1 bunk-bed with a pull-out trundle and 2 twin beds, Bedroom 5: 2 sets of bunk beds with trundle. Bottom bunk on one bed is a double. Brand new flat screens in every room.We provide a full time property manager available 24/7 for anything our guests may need. Southern Diversion offers the perfect escape and tropical dream vacation. Occupancy is 2 adults per room. Children 6 and older are considered adults. Under 6 not included in occupancy count.brbrIslamorada The Sport Fishing Capital of the World hosts an array of activities from relaxing on our private beach to world class scuba diving. From our private beach you can go catch fresh Florida lobster, Go shelling, Reef snorkeling off Cheeca Rock Reef, See live coral reefs and catch Bonefish. Southern Diversion is located directly in the Village of Islamorada (Mile Marker 82) which means you are within 5 minutes of the best cuisine Islamorada has to offer. Robbie's of Islamorada (5 min car ride) offers many different marine activities including boat rentals, jet skiing, kayak's and a delicious restaurant. Don't forget to visit Scarface in the Tarpon Feeding area. Also at Robbie's they will cook your fresh catch at the Hungry Tarpon Restaurant. If you are in the mood for a nice stroll, Bentleys Restaurant is right outside our gate or you can walk to Morada Bay where you can enjoy a relaxed beach atmosphere.brFeel free to visit other Southern Diversion Properties in The Florida Keys brhomeaway 7396601 brhomeaway 3577977brKeywords: Estate HomebrLicense No. VR 26-0394

Southern Diversion Estate Islamorada

Islamorada, Florida, United States

Bed

Bath

16

Sleeps

$663.3

Tucked away on a quiet street in Lower Matecumbe, this beautifully furnished canalfront home is everything you imagine when you think of a laid-back Keys escape. Surrounded by lush, tropical landscaping and offering total privacy, this 3-bedroom, 3.5-bath getaway has all the extras—100 feet of dockage, a heated pool and spa, and even two paddleboards ready for your adventures.brbrInside, the home is bright, spacious, and tastefully done with a clean coastal feel. Each bedroom has its own en-suite bath, making it perfect for couples or families traveling together. The kitchen is fully stocked, the living spaces are comfortable and welcoming, and there's plenty of room to spread out—both inside and out.brbrOut back, you'll find your own private oasis. Lounge by the pool, take a dip in the spa, fire up the grill, or launch the paddleboards for a peaceful cruise down the canal. The 100' dock has room for your boat and quick access to the ocean—ideal for fishing, sandbar days, or sunset cruises.brbrClose to local restaurants, marinas, and some of the best spots in the Keys—but just far enough away to feel like your own private hideaway.brbrYour slice of Islamorada paradise awaits.

Discover luxury at Stillwater Cove, a stunning 3BR retreat with beautiful pool and dockage.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$248.51

A fully furnished two bedroom, two bath townhouse located in Islamorada, also known as the Fishing Capital of the World. All amenities needed in order to enjoy a relaxing vacation. The property has a swimming pool, tennis court, pickleball court, shuffleboard, boat ramp and dock space for a boat up to 25' as stated in boat registration. brbrIf bringing a boat or renting one during you stay, proof of insurance with liability limits as well as boat registration is mandatory and should be sent to owner prior to your arrival. Use of dock space is on a first come, first serve basis with owners having priorities. Dock or ramp will not be allowed to be used until insurance and registration documents are provided to our dock master.brbrMaster bedroom is located on the third floor and has king size bed, its own private bathroom and screened porch. Second bedroom is on second floor and has queen size bed. A queen size air mattress is also available.brbrThere is a living room, dining room, second full bath and a fully equipped kitchen, as well as a large screened porch overlooking the pool and tennis court.brbrFull size washer and dryer are located in the garage. Also, a covered carport and ample parking for vehicle. Barbecue grill is stored in garage.brbrWiFi internet, televisions in both bedrooms and living room, including blue ray and DVD player.

A little Piece of Heaven to wash your worries away

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1221.1

Welcome to Alligator Reef Estate, a gated oceanfront property in Islamorada offering two homes on one beautiful waterfront parcel—perfect for larger families or groups looking to enjoy the Florida Keys together while still having their own space.brThe estate includes the Conch Home, a 3 bedroom, 2 bathroom home featuring a private fenced heated and chilled pool, outdoor kitchen and bar area, ping pong table, and bicycles for exploring the area. Just in front of it sits the Lobster Home, a comfortable 2 bedroom, 2 bathroom home that provides additional space for guests.brTogether, the property offers 5 bedrooms and 4 bathrooms, making it ideal for group vacations, family gatherings, or multiple families traveling together.brBoth homes share the beautiful oceanfront grounds which include a sandy lounging area, fire pit, observation dock, and kayaks and paddleboards for enjoying the clear waters of the Keys. Whether you're relaxing by the pool, gathering around the fire pit at sunset, or launching a paddleboard from the shore, there's something here for everyone.brAlligator Reef Estate offers the perfect balance of privacy, space, and true island living—creating a one-of-a-kind Florida Keys getaway right on the ocean. brVACATION RENTAL LICENSE: 24-0389 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.brbrIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Spacious 5BR home in Islamorada, perfect for 14 guests with ocean views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$515.95

Beautiful tranquil private beach is just the beginning of what awaits you in our completely renovated beach house. Port Antigua is one of the best neighborhoods in Islamorada. Not only does it offer a private beach, but also has a private boat ramp right inside the neighborhood. With great fishing access to the bay and open ocean just through channel 5 or channel 2. Lots of amenities and restaurants in the area to list but will provide information at the property. On the second floor there is a Master Bedroom with an on-suite bathroom. Guest/2nd Room is also located on the second floor with a full bathroom right outside the door in the hallway. Full size frontload Washer & Dryer which are also located on the second floor. Kitchen and living room are also located on the second floor. In the third floor you have a second master bedroom with an on-suite bathroom and a walk in closet. Kitchen is fully equipped for all your cooking needs. There is a total of 75 feet of dock, but a boat on a lift which will remain on the property unless you need the entire dock, then an additional fee will be applied. Please inquire before reserving if additional dock space is necessary. For more information please conact me at Agueracarlos@gmail.com. Thank you!

Paradise Retreat

Islamorada, Florida, United States

Bed

Bath

Sleeps

$316.94

Welcome to 128 Tequesta Street, a charming three-bedroom, two-bath waterfront home designed for the perfect Florida Keys vacation. Located on a canal in Plantation Key, the home offers convenient dockage so you can bring your boat and enjoy easy access to the beautiful waters of Florida Bay.brbrThe outdoor space is where this home truly shines. Relax by the pool, gather with friends under the tiki hut, or mix up a drink at the outdoor bar while enjoying the warm Keys breeze. For a little adventure, hop in one of the kayaks and paddle your way out to Florida Bay.brbrInside, the home features a comfortable open-concept layout that works perfectly for families and entertaining. The kitchen includes bar seating and flows easily into the living area, creating a welcoming space to cook, relax, and spend time together after a day on the water.brbrWhen you're ready to explore, you're just minutes from Plantation Key and the best of Islamorada — including great restaurants, local shops, marinas, and grocery stores.brbrWhether you're boating, relaxing poolside, or exploring the Keys, 128 Tequesta Street is the perfect place to experience the laid-back island lifestyle.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.

Charming 3-Bed, 2-Bath Canal Home in Tavernier, FL, with Private Pool!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$399.57

Escape to your own slice of paradise in this beautiful canal-front vacation home in Tavernier. This spacious property offers the perfect setup for families or groups traveling together.brUpstairs features a 3-bedroom, 2-bathroom home with comfortable living spaces and everything you need for a relaxing stay. Downstairs, a separate 1-bedroom, 1-bath apartment provides additional privacy, making it ideal for extended family or friends traveling together.brThe outdoor space is designed for relaxing and entertaining. The private pool is located in the front of the home and the property is gated, creating a very private setting to enjoy the Florida Keys sunshine. Pool is heated by request at an additional charge. In the backyard, you'll find a tiki hut, outdoor kitchen with bar seating, and a large TV, perfect for grilling fresh seafood, watching the game, or enjoying evening cocktails.brBoaters will appreciate the canal-front location with dockage and two boat lifts, making it easy to bring your boat and explore the beautiful waters of the Florida Keys right from your doorstep.brWhether you're lounging by the pool, entertaining under the tiki hut, or heading out for a day on the water, this Tavernier home offers the perfect blend of comfort, privacy, and classic Keys living.brAlso note, this beautiful home is available for monthly rentals only.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 spacious 4-bedroom canal home in beautiful Islamorada!

Islamorada, Florida, United States

4

Bed

Bath

Sleeps

$1836.16

Gorgeous 30’ oceanfront heated pool. House on an exceptionally private, natural beach and oceanfront seawall in Islamorada - observation dock for paddle boarding, fishing and kayaking. Property is flanked by natural preserve on one side and has wide open expansive ocean views. The private beach is located along a wildlife protected turtle nesting beach that left natural for turtle nesting season. brbrThere is an incredible 180 degree water view from almost every room in the house. Spectacular sunrises flood the rooms with golden light reflected off the ocean. The sun rises over the water every morning within your view. The sunsets are equally stunning over the peninsula leaving the view with purple and pink clouds. Constant onshore breeze drifts through the house with pure, invigorating ocean scents. brbr2 Paddle boards and 2 kayaks are included with rental as the waters off the house are perfect for exploring by kayak. 2 cabanas for rest and relaxation - one by the pool and one the dock. The wildlife is stunning and you are bound to see amazing creatures during each outing! There is also an amazing State Park (an island) just a paddle away. Alligator Reef Lighthouse is on the horizon and the ocean views from the end of the observation dock are simply incredible. The oceanfront pool is heated to 86 degrees.brbrThe house is a 100% non-smoking property. The observation dock is for non-motorized vessels only as the tides can get very low during full moons.brbrTHIS PROPERTY RENTS SATURDAY TO SATURDAY brRobbie's of Islamorada is down the street from the property a half mile and offering an outdoor restaurant, jet ski rentals, tarpon feeding, shops, fishing charters, snorkeling trips & sunset cruises to the Lighthouse.brbrAbout the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel and is exceptionally clean and easy to enjoy.brbrWe privately own a total of 5 boutique vacation rentals in Islamorada:brVRBO listing #1576833 (5 bedroom)brVRBO listing #1054019 (5 bedroom)brVRBO listing #1977457 (7 bedroom)brVRBO listing #689629 (5 bedroom)brbr (no boat dockage due to tides)brbrLICENSE #: 26-0279 - Islamorada

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Islamorada, Florida, United States

Bed

Bath

10

Sleeps

$2697.57

Welcome to Mermaid's Bay Boutique Estate, an extraordinary bay-front retreat located in the heart of Islamorada. Set behind a private gate and spanning more than 3.5 acres of lush tropical landscape, this secluded estate offers a rare blend of privacy, history, and natural beauty, with over 300 feet of waterfront and sweeping views of the Florida Bay.brbrOriginally built in the 1940s and lovingly preserved, Mermaid's Bay is a hidden gem in the Keys. The estate includes three thoughtfully appointed homes, offering a total of eight bedrooms across the property. Each home is designed to provide its own sense of space and serenity, while still feeling connected to the overall estate. brbrThe spacious main house features four bedrooms, each with its own ensuite bathroom, and is ideal for gathering and entertaining. Two additional cottages, each with two bedrooms and one bathroom, offer charming, private accommodations for couples or smaller families. All three homes include private porches, individual yards, dedicated parking, and well-equipped kitchens, making it easy to settle in and feel at home. Details like outdoor grills, soft linens, and complimentary toiletries are provided to make your stay as seamless as it is comfortable.brbrBeyond the homes, the estate features a resort-style pool and spa, a private beach with hammocks and lounge chairs, a large protected boat basin, a small boat ramp and an array of amenities including kayaks, paddle-boards, and bikes. Whether you're soaking in the sunset from the shoreline or heading out for a day on the water, Mermaid's Bay offers the perfect backdrop for an unforgettable stay in the Florida Keys.brbrRentals are from Friday to Friday. Differing dates may be approved on a case-by-case basis.brbrThe estate can be rented as a whole or as individual units. Please contact us for more information.brbrThis property is locally managed by Solace Properties. Once your booking is confirmed, you'll receive a rental agreement via email to review and sign. Rental payments are processed directly through Solace Properties, while VRBO collects their service fee separately. For any questions or assistance, Solace Properties will be your main point of contact.

Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1302.29

brbrThe Dock View House is a spacious four-bedroom, four-and-a-half-bath home located within Mermaid's Bay Boutique Estate—a private 3.5-acre bayfront retreat in the heart of downtown Islamorada. The estate features 300' of bayfrontage, a pool and hot tub, protected boat basin and more. Originally built in the 1940s, the home retains its island charm while offering modern comforts and generous indoor-outdoor living.brbr brbr• Resort-style shared amenities, including heated pool and spabr• Sandy beach with hammocks, lounge chairs, and tiki hutbr• Large protected boat basin and small boat rampbr• Complimentary kayaks, paddle boards, and bikesbr• Multiple living spaces: sunlit solarium, large living room, dining roombr• Bayside entry directly to beach and dockbr• Private grill, patio seating, and dedicated parkingbrbr brbr4 Bedrooms (each with private ensuite)brbrLeft Wing:br• Downstairs Bedroom: 2 Queen Bedsbr• Upstairs Bedroom: King Bed + Small adjoining room with sleeper sofabrbrRight Wing:br• Downstairs Bedroom: King Bedbr• Upstairs Bedroom: King Bed + Small office spacebrbr4.5 Bathroomsbr• Four private ensuite bathroomsbr• Two half baths—one in each wing's stairwell hallwaybrbrLiving Areasbr• Chef-style kitchen with modern appliancesbr• Dining room overlooking the waterbr• Large living room and bright solariumbr• Double-sided (non-working) fireplace at the center of the homebr• Large windows with open water views from most roomsbrbrIn-Home Amenitiesbr• Washer/dryerbr• Filtered water dispenserbr• Smart TVs and high-speed Wi-Fibr• Personal safesbr• Starter supplies provided, including toiletries, paper goods, and coffeebrbr brbrThe protected boat basin accommodates boats of various sizes and provides direct access to the Florida Bay. Dockage and trailer storage are included with the stay. A small ramp is available.brbr brbrIdeally located in downtown Islamorada and within easy walking distance to restaurants, breweries, local shops, and popular attractions.brbr brbrRentals are from Friday to Friday. Differing dates may be approved on a case-by-case basis.brbrThis property is locally managed by Solace Properties. Once your booking is confirmed, you'll receive a rental agreement via email to review and sign. Rental payments are processed directly through Solace Properties, while VRBO collects their service fee separately. Solace Properties will be your primary point of contact throughout your stay.

Spacious Bayfront Home with Heated Pool, Deep Dockage, Kayaks and More

Islamorada, Florida, United States

4

Bed

Bath

10

Sleeps

$293.52

brbrTime Well Wasted is an inviting three-bedroom retreat located in the Port Antigua neighborhood of Lower Matecumbe Key. A highlight of every stay is access to the private bayfront homeowners' beach—a peaceful stretch of sand along the Florida Bay with tiki huts, calm shallow water, and space to relax under the sun.brbr brbr• Access to private homeowners' beachbr• Dockage for boats up to 20 ft (quick access to Florida Bay)br• Use of neighborhood boat rampbr• Kayaks and paddle boards provided for guest usebr• Spacious covered porch with seating, grill, and golden-hour viewsbrbr brbr3 Bedroomsbr• Primary Suite: King bedbr• Guest Bedroom 1: Queen bedbr• Guest Bedroom 2: Two queen bedsbrbr2.5 Bathroomsbr• Master ensuite bathroombr• Jack-and-Jill shared bath between guest rooms (each with private vanity and toilet)brbrLiving Areasbr• Open living and dining areabr• Fully equipped kitchenbr• Large covered porch for outdoor grilling and loungingbrbr brbrLocated just minutes from the Florida Bay. Enjoy quick, easy access to world-class backcountry fishing on your skiff, or explore the calm waters by kayak or paddle board.brbr brbrPort Antigua is a quiet, upscale neighborhood on Lower Matecumbe Key—just a short drive from downtown Islamorada's restaurants, marinas, and shops.brbr brbrFor the safety and security of our guests and the property, this home is equipped with exterior security cameras. These are located outside the home only and do not record audio.brbrThis property is locally managed by Solace Properties. Once your booking is confirmed, you'll receive a rental agreement via email to review and sign. Rental payments are processed directly through Solace Properties, while VRBO collects their service fee separately. For any questions or assistance, Solace Properties will be your main point of contact.

Peaceful Home with Skiff Dockage + Access to Private Bayfront Beach

Islamorada, Florida, United States

Bed

Bath

Sleeps

$317.6

Your cozy getaway awaits in quiet Venetian Shores at this bright and airy house. Deep water canal! Easy and QUICK access to the Ocean only 2 canals away! With 3 bedrooms including 2 queen beds and 2 twin beds, this marvelous property offers a tranquil escape. Enjoy 2 bathrooms, 1 with tub and 1 with a shower. Plus an queen size futon in the living room. Bright, beautiful view and a 100 foot, deep water dock on canal, great fishing!! Separate living area. Full kitchen with appliances. Gas grill outside. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out. Pet friendly. Free access to Founders Park with pool, beach and pickle ball courts only 1 mile from home. https://fl-islamorada.civicplus.com/435/How-to-Obtain-a-Founders-Park-Guest-Pass

Comfortable, Spacious 3-BR, 2-BA-1 level home- DEEP dock on canal, Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$412.27

Escape to Sun Outdoors Islamorada in the Sport Fishing Capital of the World. Live your best Keys life in this beautifully designed 2 bed, 2 bath oceanfront home in a prime resort location. Start your mornings with coffee on your private balcony as the sun rises over the Atlantic, then spend your days boating, fishing, snorkeling, or diving some of the best waters around. When it’s time to kick back, you’re just minutes from iconic tiki bars, local restaurants, shops, and grocery stores—everything you need for effortless island living. Bring your boat—there’s a marina on site with a slip for up to a 20’ boat, plus resort-style amenities including a pool, beach area, food truck, and a clubhouse with games, ping pong, gym, and fun community events. Sunshine, salt air, ocean views, and laid-back luxury… you just found your new favorite vacation location. brbrPlease inquire about dockage availability and pricing. brbrSun Outdoors Islamorada - Waters Way brMM87 Oceanside brbr28 night minimum. Please inquire for rates and availability.

Sun Outdoors Islamorada ~ Beautiful Oceanfront 2 Bedroom Home

Islamorada, Florida, United States

Bed

Bath

Sleeps

$430.74

Dockside Daydream – Waterfront Paradise in the Florida KeysbrWelcome to Dockside Daydream, your tropical escape in the heart of the Florida Keys. This 3-bedroom, 2-bath waterfront retreat blends laid-back island charm with modern comfort, offering the perfect setting for both relaxation and adventure.brFeatures:br• Prime Waterfront Location – Wake up to sparkling water views and gentle ocean breezes.br• Private Dock & Boat Ramp – Launch your boat, kayak, or paddleboard right from the backyard.br• Private Beach Access – Enjoy sun-soaked days and unforgettable sunset views on your own stretch of sand.br• Outdoor Living – Spacious deck and patio for lounging, dining, and sunset cocktails.br• Island Style Interiors – Bright, airy spaces with coastal-inspired décor.br• Fully Equipped Kitchen – Cook up fresh Keys seafood with ease.br• Comfortable Bedrooms – Cozy, inviting spaces designed for restful nights.br Perfect For couples seeking romance, families craving fun in the sun, or friends ready for a Keys adventure. Whether you’re snorkeling, fishing, boating, or simply unwinding by the water, Dockside Daydream is your gateway to unforgettable memories.

Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures

Islamorada, Florida, United States

Bed

Bath

Sleeps

$315.0

FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full bathrooms and a loft for gaming etc. freshly painted all new furniture & fixtures, all new. Inside you have washer/dryer stainless steel appliances fully equipped kitchen. Dishwasher, microwave everything for your comfort. The premises is a gated community with private beach, boat ramps, Olympic pool clubhouse, Nearby shopping, restaurants, Gas etc.

FULLY RENOVATED piece of paradise. 2 bdrs, 2 king beds, 1 Queen bed 2 full baths

Islamorada, Florida, United States

Bed