Vacation Home Rentals By Owner In Islamorada, FL

This Ocean Retreat offers breathtaking views from every room, with a 60' covered balcony that overlooks the 32' Pool/Spa and 100' Concrete Seawall on the Atlantic Ocean. We are just steps away from a beautiful white sandy beach, which is an active turtle nesting area. The home is situated near the end of a quiet road (locally referred to as “Millionaires Row”). Construction was completed in August 2020 and is appointed with high end contemporary furnishings. The open concept living area offers wall to wall sliding glass doors facing the Atlantic, to enhance the feeling of openness all ceilings are 10' or higher throughout the house. brbrBe it a romantic getaway or a family adventure, this location is the perfect spot to build lifelong memories. The expansive upper deck is a great spot to watch Manatees, Ospreys, Egrets, Herons, Sharks and the occasional pod of Dolphins cruising the flat below. On windy days Kite Boarders launch at nearby Anne’s Beach and will treat you to a show as they fly back and forth in the sunshine below. brbrThe #500/day ice machine will keep your fish box or cooler cold. and our dock is equipped with 30amp shore power and offers 4' depth. We have three kayaks (1 single & 2 doubles), two standup paddle boards, two bicycles, also available is the 12k boat lift.

You will never want to leave

Islamorada, Florida, United States

Bed

Bath

Sleeps

$625.97

Welcome to a one-of-a-kind Florida Keys escape! This unique home, originally used as the Islamorada Courthouse, has been thoughtfully transformed into a stunning waterfront getaway while keeping its historic charm. Located in the heart of Islamorada, this property offers access to what the Keys are known for: the best fishing, dining, and great sunsets.brbrFor the comfort and safety of all guests, our accommodation is designed for guests aged 12 years and older. Pets are not permitted.brbrEscape to this bright and welcoming 3-bedroom, 2-bathroom home, perfectly designed for relaxation and connection. Located right on the water, this Keys-style getaway blends indoor comfort with unbeatable outdoor living.brbrHighlights of your stay:br✔ Smoke Free environmentbr✔ Three comfortable bedrooms with cozy beddingbr✔ Two full bathrooms (no ensuite)br✔ A stylish and comfortable living room with ample seating for winding down after a day in the sunbr✔ A full kitchen with all the essentials, plus a dining table for six for shared meals and game nights.br✔ A screened in porch overlooking the water.brbrStep outside to your private waterfront tiki hut, fully outfitted with:br✔ Outdoor TV for game days or movie nightsbr✔ Refrigerator & ice maker for easy refreshmentsbr✔ Dining and lounge areas ideal for morning coffee, sunset dinners, or just soaking up the breeze.brbrOur waterfront property offers private boat dockage for vessels up to 30 feet, so feel free to bring your boat and make the most of your stay! From your own backyard, you can easily cruise through the crystal-clear waters of the Florida Keys, discover hidden sandbars, fish in world-class spots, or enjoy stunning sunsets from the water. Whether you're island-hopping or just exploring the beautiful surrounding areas, your adventure starts right here!brbrThe villa is stocked with all the basics you will need to start enjoying your vacation right away without any worries. The villa also boasts amenities like an iron/iron board, a hairdryer, beach towels, umbrella, and beach chairs. To start your day, there is a Keurig duo coffee maker (K-cup and drip), french press, and a kettle.brbrThe design of the villa consists of two separate units — one on the ground floor (yours) and another on the upper floor. Both units have separate entrances and are not connected in any way. All outdoor amenities are exclusive for you and your guests. brbrBook your stay now and enjoy waterfront living, island breezes, and all the comforts of home—Keys-style!

Off The Charts-Waterfront Tiki Bar & Private Dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1282.5

Islamorada Rental License: VR - 065 *** SATURDAY TO SATURDAY RENTALS ONLY!brbrIf your preferred dates are not available, check our other home, The Last Resort Too - VRBO #4357870, MM 77, or contact us with an inquiry here, SPECIFYING The Last Resort ToobrbrCHECK OUT A FEW WORDS FROM THE OWNERS BELOW THE INITIAL INFORMATION...brbr4 bed/5 bath beachfront on over 1 acre with a private beach, heated pool & dockbrSeparate upstairs Den area sleeps up to 6 kids.brbr* 7 Day minimum rental - Saturday to Saturday *brSORRY, NO WEDDINGS OR LARGE EVENTS ALLOWED br Max 8 adults + 4 childrenbrYou must be 25 years+ to rent this home and must be staying for the duration of the rental.brbrOur house is one of the most highly sought-after vacation homes in Islamorada that regularly books years in advance. The Last Resort is a firm favorite of multi-generational families and friends looking to create memorable moments that last a lifetime in a lush, private, and tropical setting.brbrAs owners, we have spent 24+ years providing the best possible Keys experience for guests. Michele handles the day-to-day operations of the property and ensures guests have everything they need for a stress-free vacation. We believe that guests should not have to worry about 'extra or hidden' charges, so our rates INCLUDE many of the things other vacation rentals charge for, such as pool heat, BBQ gas, kayaks, and baby equipment. Though the property is self-catering, we supply many household items so you don't have to worry about purchasing them, such as laundry detergent, dishwasher detergent, garbage bags, kitchen paper, cleaning fluids, etc.brbrWe also don't charge a security deposit or pet fee. We operate on an honor & integrity system, giving our guests an authentic Keys experience that keeps them returning year after year as repeat guests.brbrFrom years of international travel with our kids, one of my pet peeves was the amount of equipment that I had to pack just to go on vacation. Another was arriving at houses that were sparsely stocked or having to rent additional equipment. Greg and I made the commitment to provide as many supplies and equipment for our guests, from all kitchen equipment to baby equipment, from hairdryers & straighteners to lifejackets and water shoes, all to alleviate the need for guests to stuff their suitcases and truly make it a 'pack your shorts, flip-flops & toothbrush' kind of house.brbrThe Last Resort is truly in a beautiful setting, and we look forward to the opportunity to host you, your family, and your friends someday.brbrMichele & Gregbrbr.... AND NOW THE HOUSE...brbrBuilt in 1922, this historic Conch Style oceanfront executive retreat boasts overwhelming views of the Atlantic, large open verandas, 165 feet of private sandy beach, a 15 x 30 seaside heated swimming pool, 37 ft. concrete protected dockage on the canal adjacent to the house, and a gated entrance. Quiet seclusion awaits you at this unique destination.brbrThis 4-bedroom, 5-bath home with 4,000 square feet of living area is situated on over an acre in a private, tropical setting. Located in an upscale neighborhood in famed Islamorada, this fine home offers you the ability to relax, entertain, and enjoy the many recreational activities found only in the Florida Keys! br brRecognized by international publications as a preferred location for resort and swimwear photo sessions, the interior is casually furnished, tropically decorated, and offers every imaginable convenience.brbr* Ralph Laurenbr* Victoria's Secretbr* Abercrombie & Fitchbr* Michael Korsbrbr* Opening shot Bloodlinesbr* Promo shot HGTV Dream Homebrbr* Variety of European magazinesbrbrYou'll find an abundance of great island shops, full-service marinas, and popular local restaurants nearby! br brIdeal home for extended families, as most of the living space is on the ground level. Also, wide-covered front and back porches are ideal for outdoor entertaining/relaxing. The rear veranda overlooks breathtaking ocean views, palm trees, and a private sand beach. The front veranda overlooks a beautiful, tropical landscaped yard. Our home also has a rooftop deck overlooking the palm-lined sand beach and brilliant shades of the tropical ocean.brbrAmenities: Two-story home with front and back covered porches, a 15x30 heated in-ground pool, a 165-wide private sand beach, and beautiful landscaping. House includes phone, high-speed wireless Internet/DSL line, dual-zone central air conditioning, ceiling fans in all rooms, 3 cable/smart TVs (both Masters & Living room)(2 smart TVs in the kids' Den, DVD player, and Bluetooth speakerbrbrFull kitchen includes a microwave, dishwasher, refrigerator, beverage fridge, coffee maker & Keurig 2.0, toaster, cooking utensils, and linens provided. 2 washers, 2 dryers, and 2nd fridge in the Laundry room. Jacuzzi tub in the downstairs Master bath.brbr brGas grill (BBQ). Pets are allowed with advanced permission. 37-foot concrete private dockage with mains water and direct ocean access is available on our canal lot adjacent to the oceanfront home, with plenty of room for a boat trailer.brbrThere is one exterior camera on the front porch pointing towards the driveway. and a 2nd camera on the exterior of the laundry room door. There are no other cameras anywhere on or on the property.brbrFeel free to send us an inquiry for any further information before making a booking decision. We are always happy to help.brbrMichele

Next available - August 2026 - Oceanfront - Heated Pool - Dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1454.47

Relaxing is made easy at Coral Cove 8, moving from open, airy living spaces to your own private pool. Bright modern finishes meld with traditional Key West style, Coral Cove 8 offers island living in style. This retreat is just a short walk or kayak from our docks and boat basin to the heart of downtown Islamorada, where you will find great dining, music, spas, art galleries and boutique shopping. Coral Cove 8 offers three bedrooms with ensuite baths, plus a powder room on the main floor. Full kitchen, seated island and living space open out onto our private deck and pool with our docks just beyond and all feature magnificent Bayfront views. Relax, recharge and rejuvenate -- Coral Cove 8 can make your getaway a dream vacation.

Beautiful bayfront house, private pool and dock, right in Downtown Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$387.16

Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located in Islamorada's Port of Call community. 5 minute walk or bike ride to several of Islamorada's best restaurants!brbr*Only 10 units are nestled on this oceanfront piece of paradise along Millionaire's Row in Plantation Key/Islamorada. brbr*Perfect location in heart of Islamorada, the Sport Fishing Capital of the World! 90 minutes from Miami, 20 minutes from Key Largo, 90 minutes to Key West brbr* 2 Bedrooms and 2 1/2 bathsbrbr*Bedding: King, Full bunks, Twin bunksbrbr*Sleeps up to 5 but max of 4 adults due to bunksbrbr*Modern kitchen with quartz countertops, all the gadgets for a gourmet meal including Keurig AND regular coffee pot, all pots and pans, utensils, Kitchen-Aid appliances, built in ice/water on freezer, Washer/dryerbrbr*3 Flat-Screen TV's, all with HD stations, over 1800 On-Demand Movies, voice control (one in each bedroom plus living area)brbr*All new mattresses and linensbrbr*Beautiful direct Atlantic ocean view from unit with Palm Tree breezes from screened oversized porches brbr*1550 square feet, covered carport with room for two carsbrbr*Wifi throughoutbrbr*Built out California Closetsbrbr*Seamless Glass Enclosed Shower in Master Bath, tub/shower in glass enclosed guest bathbrbr* Experience 360 degree views from the roof top deck and look out at the finest Islamorada sunrise and sunsets! brbr*Black out Draperybrbr*Get ready to feel the sand between your toes!brbr*Unit has its own barbeque grill and picnic table. brbr*Community includes heated pool, chickee hut with common area barbecue grills and an ocean front sandy beach. Dock is newly built after Hurricane Irma and contains 10 boat slips. Fish off the the new dock or use the two ladders to lower yourself in and out of the ocean for snorkeling or a casual swim in the Atlantic Ocean!brbr* Grounds are home to several Peacock families with babies! You may see them strolling around or take a walk just north of the property and you will be sure to find them!brbr*This hidden gem awaits you with sandy beach, Atlantic Ocean, sunrise and sunsets and all the comforts of your own home or five star hotel room.brbrCheck out our other VRBO Vacation Rental, Island Dreamz Bay House, Vrbo 2076205brbrState of Florida DPBR Vacation RentalbrLicense #DWE5404235brbrVillage of Islamorada Vacation RentalbrLicense #VR-25-0241

5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$743.27

126 Palermo DrivebrCheck out this new to the Vacation Rental Market home in Venetian Shores on canal with 70' dock, pool, tiki hut and hot tub.brbrCall Jennifer for more information 305-240-0592.brbrCompletely remodeled in 2021, this concrete home has very spacious bedrooms (each with a KING bed), beautifully appointed with all new furniture, new gourmet kitchens and new bathrooms.brbr70’ of Deep Water dockage included in rate. Bring your big boat(s)! Large, deep canals with Drawbridge out to ocean via Snake Creek! Parking for one trailer on lot.brbrTwo Bedrooms and Two full Bathrooms upstairs with large kitchen and open living floor plan. There is also a full sized washer and dryer and large closets. Wonderful screened porch for your morning coffee where you will be sure to see some great wildlife (tarpon rolling, birds and an occasional dolphin or turtle)!brDownstairs (separate) you will find a Large ONE King Bedroom and Full Bathroom with full kitchen and large living room. Walk out the sliders to the pool deck, and amazing view of the canal.brbrOur on site care taker is in a separate apartment (ground level street side) and is there to help with maintaining the property and is a great resource for local fishing spots!brCome enjoy your next vacation in the best neighborhood in the Keys! Close to restaurants, parks/beach, the famous Islamorada Sand Bar and so much more!

Venetian Shores Home -DOCK remodeled 3/3 POOL/Hot Tub! Deep water Dockage

Islamorada, Florida, United States

Bed

Bath

Sleeps

$331.58

Escape to Anglers Reef, Islamorada’s premier gated community where coastal charm meets resort luxury. This fully renovated two-bedroom, two-and-a-half-bath home—one of the largest floorplans in the neighborhood—comfortably sleeps 8 guests.brbrUpstairs, two spacious suites offer private retreats. The primary suite features a king bed with premium linens, private balcony overlooking the Atlantic, and an ensuite bath with walk-in shower and double vanity. The guest suite includes two queen beds and a full bath.brbrOn the main level, the open-concept living area includes a sleeper sofa, remodeled kitchen with KitchenAid appliances, bar seating, dining area, and a smart-TV-equipped lounge.brbrGuests enjoy resort-style amenities—two sandy beaches, a heated pool, private marina, kayaks, and palm-lined walking paths.brbrBook your Anglers Reef getaway today and experience the best of Islamorada’s oceanfront living.

Renovated Anglers Reef 2BR + Sleeper + Ocean Views, Pool, Marina, Sleeps 8

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$723.62

PROPERTY NAME: Bellabr109 Valencia Drive Tavernier, FL 33036brbrLOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Venetian ShoresbrbrMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedbrbrMILE MARKER: 86brbrDESCRIPTION: Luxurious 4-Bedroom Home in Venetian Shore – A True MasterpiecebrStep into your dream home in the highly sought-after Venetian Shore neighborhood! This stunning 4-bedroom, 5.5-bath residence offers a perfect blend of sophistication, comfort, and entertainment – making it ideal for family living and hosting guests.brKey Features:brChef's Kitchen: Equipped with top-of-the-line appliances from Wolf, Sub Zero, Bosch, and more. Whether you're preparing a casual meal or hosting a dinner party, this kitchen will inspire your culinary creativity.brEntertainment Paradise: Enjoy hours of fun in the Game Room, complete with a pool table, foosball, and classic arcade machines including Miss PacMan, Frogger, and Donkey Kong. For even more excitement, try your luck with the slot machine, or unwind at the full bar with plenty of seating.brPrivate Office & Spacious Layout: Work in peace in the dedicated Private Office, and take advantage of the expansive living areas that create a warm and inviting atmosphere.brMaster Suite Retreat: The Primary Bedroom offers the perfect sanctuary, featuring an en-suite bath with a claw-footed tub, separate toilet room, full shower, and dual vanity for a spa-like experience.brGuest Rooms & Bath: Two spacious Guest Rooms connected by a Jack & Jill bathroom ensure comfort and convenience for family and guests.brUpstairs on 3rd Level you have the Ultimate Mans cave, Two Tv's , Sofa, Bar Area with Mini Refrigerator and Ice Maker for enjoying cocktails while watching your favorite sportsbrRoof Top Sun Deck for sunbathing or enjoying the beautiful stars at nightbrOutdoor Paradise: Relax or entertain in the open and spacious pool area, featuring a heated pool with a built-in seating shelf for ultimate comfort.brOutside Full Bathroom located next to the Pool areabrUnmatched Comfort & Style: Every room is beautifully furnished with top-tier pieces, creating an atmosphere of both luxury and warmth.brDeep water for the bigger boats with no fixed bridges to the OceanbrOnly a short boat ride to the Famous Sand BarbrbrSleeping Arrangements: Sleeps 9 comfortablybrPrimary Bedroom: King, with ensuite bath with Tub, Shower, Dual sinks and a separate toilet roombrGuest Rooms upstairs, both have Queen beds with a Jack and Jill Bathroom brGuest Room downstairs, Queen bedbr3rd Level has a pull out single couch for sleepingbrbrAmenities Include: Heated Inground Pool, Dockage for boats up to 30 ft 2nd floor balcony for outside entertaining just off Kitchen. brActivities: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures.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.

Luxurious Home Located In Venetian Shores

Islamorada, Florida, United States

Bed

Bath

Sleeps

$407.33

Discover the Keys from a unique perspective at this Islamorada rental home, a true haven for fishing enthusiasts! Positioned near the island's end, this residence offers secure dockage and immediate access to the Florida Bay and Atlantic Ocean – a fisherman's paradise with some of the best tarpon fishing in the world.brbrAfter a day of outdoor adventures, relax in this well-appointed home with various views. The third floor houses the master suite with its own balcony, providing an intimate spot for sunset views and an ideal vantage point for planning your next fishing expedition. Mullet are always around, offering fresh bait for your angling pursuits right from the premises.brbrThe main level features an open layout with a living room, gourmet kitchen, and a generously sized bedroom and bath. The lower level boasts three more bedrooms, a bathroom, and a living area accessed by an interior spiral staircase – perfect for solitude or communal enjoyment after a successful day on the water.brbrExplore nearby trailer storage options for your convenience. With a two-vehicle limit on the property, your boat trailer can be stored off-site. The dock accommodates vessels up to 34 feet, and the boat lift handles boats up to 26 feet – ensuring you're well-equipped for an extraordinary fishing experience.brbrA sandy beach on the premises is perfect for easy paddleboard launches or simply unwinding. Plus, relish the chance to witness dolphins frolicking in the nearby waters directly from the porch, adding an extra touch of magic to your island getaway.brbrImmerse yourself in Islamorada's charm at this retreat, where every detail invites you to experience the perfect blend of adventure, relaxation, and unparalleled fishing opportunities. br

Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$484.11

Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of parking. Outdoor shower and BBQ. Upstairs has 2 bedrooms (1 with a king and 1 with 2 queens), a hallway full bathroom, living room, kitchen combo with stove, dishwasher, and fridge, W/D. Downstairs has a mother-in-law suite with 1 queen bed and a queen sofa pullout with own kitchen, stove, and fridge. Full bathroom in the suite. Ramp at Sea Bird Marina for a fee.brbrPayment with credit card thru the VRBO website only. Any other request is a SCAMMER.br

New saltwater pool, pet friendly, waterfront house with dock

Islamorada, Florida, United States

3

Bed

Bath

8

Sleeps

$397.1

Welcome to Casa Del Pirata! brbrLocated 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 paddle boards 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.brbrThis could be just the getaway you need, for more information contact us at (305) 664-0077.brbrHave any questions Feel free to ask away! Coastal Vacation Rentals of the Florida Keys is located in the heart of Islamorada and has a full office staff to ensure you have the best vacation possible.brbrReservation Deposit & Cancellations: A reservation deposit equal to one-half (50%) of the total reservation amount is due at the time of booking. TENANT shall be entitled to a refund of the one-half (50%) reservation deposit, less any non-refundable fees, if the reservation is cancelled at least 60 days prior to the occupancy date. The remaining balance, including any required security deposit, is due no later than 60 days prior to the occupancy date. If the cancellation occurs within 60 days of the occupancy date, the full reservation amount shall be non-refundable. If the booking is made less than 60 days prior to the occupancy date, the full reservation amount shall be due at the time of booking, and TENANT shall not be entitled to a refund of any amounts paid in the event of cancellation. As an exception to the foregoing, TENANT shall be entitled to a refund of all amounts paid if COASTAL re-rents the property for the same amount and for the full rental period. If the property is re-rented for fewer days or at a lower rate, COASTAL may deduct from the refund the difference between the total amount due under TENANT’s original reservation (including all taxes and fees) and the amount received from the subsequent rental. brbrInstant quote prices and calendar availability are subject to change without notice and are not guaranteed. Please contact Coastal Vacation Rentals of the Florida Keys to speak to one of our associates to confirm pricing and availability.

Casa Del Pirata / 3 bed / 2 ba Canal Home in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1077.98

Located directly on the water in fabulous Venetian Shores, Islamorada’s premier community. Our luxurious 5 bedroom/ 5.5 bath home in Venetian shores overlooking the blue waters of Snake Creek and the Islamorada wildlife sanctuary, has everything you need for your Florida Keys vacation. This home is only minutes from the best fishing in the world with no fixed bridge for access. You will find peace and privacy as the tide rolls in and out with nothing but mangroves behind you. brbrMake a gourmet meal near the pool in the outdoor kitchen or relax on the screened balcony just off the dining room or have a family movie night with any of the ultra hi-definition televisions. Cable, Wi-Fi and high speed internet are included. Retire to the master suite and watch the world famous sunset over the mangroves all from the comfort of the private rooftop area. Then enjoy a steam in the custom steam shower or the comfort of your king size Sleep Number bed. brbrYou’re here to enjoy the great outdoors. Enjoy a dip in the heated pool or hot tub. Show off your skills at the gourmet outdoor kitchen with gas appliances and a Kamado Joe charcoal grill for that die hard BBQ expert! Worried about no see ums or Mosquitoes interrupting your time Not here. With the mosquito net, tiki torches lit, and fire pit, they won’t dare to say “hi. If they do, push the mosquito net button and you’ll be able to enjoy the outdoors which is the purpose of your trip!brbrAfter a day of fishing or on the water, relax in the pool while food is cooked on the grill or the kamoda Joe while watching the game on the TV.brbrRelax and enjoy watching the wildlife, and feeding the resident snapper and tarpon behind the house after the sun goes down. If your lucky, you may meet the manatee or pods of dolphin that swim by from time to time. Dock your boat on our 55 feet of dock. Please feel free to use the 650-pound ice machine conveniently located just inside the garage. There are several two-person kayaks for you to explore with. We welcome you to experience our home and make memories that will last a lifetime!!!

Islamorada Paradise on Snake Creek

Islamorada, Florida, United States

7

Bed

4

Bath

10

Sleeps

$250.77

Sun Outdoors resort offers first class amenities, in the heart of Islamorada, near many restaurants, and across the street from Founders Park. brbrMake yourself right at home behind controlled access gates. Enjoy amazing views of the Atlantic, and be a social butterfly when you want to join others at the Resort Clubhouse. The resort offers a social calendar and events, or privately entertain in your own home. Lay back and enjoy the Isla Life your way! brbrThe home is two levels, with parking underneath. Primary bedroom upstairs, secondary bedroom downstairs. Both floors have full bathrooms. Home is furnished with everything you would need, brbrDisclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.brbrMinimum 28-day reservations required.brBedding Configuration: King bed, 2 Twin beds, Futon

Amazing 2-bedroom waterfront resort home! Minimum 28-Day Reservation Required

Islamorada, Florida, United States

Bed

Bath

Sleeps

$273.33

This beautiful home has stunning views of the Atlantic Ocean. This home has 2 full two bedroom, two baths and is fully furnished - just bring your suitcase. brbrWhile here, you will have full access to all of the Sun Outdoors Islamorada resort amenities and activities. Including, a heated pool, clubhouse, outdoor game lawn, billiards, and ocean front tanning chairs and boardwalk. A social calendar for all guests is always available for those that wish to be more social, while fine dining is only a minutes drive in Islamorada.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee.

Enjoy the Ocean from the deck of this 2BR. Minimum 28-Day Reservation Required

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$250.77

Prime location for a relaxing stay, take in the views of the Atlantic from your private balcony. This 2 bedroom,2 bath, has everything that you would need to make this your best vacation ever! brbrWhile here, you will have access to all the resort clubhouse amenities or, play some billiards, work out in the fitness room or just hang out along the boardwalk to read a book or watch the sun setting from a rocking chair. Walk across the street to Founders Park and enjoy beach access or a game of pickle ball. It’s all up to you. brbrThe home is privately owned and decorated, brA min of 28 nights is required for these homes.

2-bedroom home with stunning ocean views in a resort!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$578.01

This New construction has all the bells and whistles to make your stay unforgettable. Located in the heart of Islamorada and the Florida Keys this 2 story home offers access to both the Gulf and Atlantic, has its own private recreational room with pool table and right outside you will find a modern heated pool with spa! brbrThis home offers 3 bedroom and 3 full baths (2 en-suite) upstairs and 1 room and 1 full bathroom first floor in recreational room. Bedroom breakdown: 1 king room, 1 queen room, 1 twin room, 1 rec room with queen sleeper. Sleeps 8 comfortably and we offer Corduroy’s famous convertible bean bag that converts to twin. The recreational room has a sleeper sectional, large 75 inch flat screen tv and new pool table. brbrHome has a full kitchen on second floor with everything you need to make a home cooked meal. Kitchen island features 4 counter stools and dining area accommodates 6-7 guests. All rooms including family rooms have their own NEW smart TVs. Family room TV 65 inch flat screen. In October 2022 will add a bar and mini fridge in the recreational room for further convenience.brbrBring your boat up to 40 feet! You will have your own slip located just steps (less than 30 seconds away) from the home. There is parking right in front of the boat for unloading/loading if needed. It is very convenient! brbrThe home is gorgeous and you will be among the first to stay! Everything is brand new just for you! We make it convenient to just move in by offering a full Keurig Coffee Bar where you can make your own latte and cappuccino! Offer shampoo and conditioner in all bathrooms, offer laundry detergent, dishwashing soap and dishwasher detergent, toilet paper and paper towels!brbrPlease inquire if thinking of bringing a pet:)brbrWe welcome YOU to stay in paradise!

NEW Luxury Modern Coastal Home in Islamorada

Islamorada, Florida, United States

4

Bed

4

Bath

8

Sleeps

Select Dates for Price

private entrance and parkingbrprivate street on canal/oceansidebrlarge room with private bathbrTV, internet, refrigerator, microwavebrkayak and boat right off the dockbrbrIslamorada is located right in between Key Largo and Key West brbr2 beaches one block awaybr(1) public with meandering boardwalk and covered picnic tablesbr(2) private beach just for renters in our homeowners associationbrbrTheater of the Sea of Islamorada brSea life and other live showsbrbrWorldwide Sportsman - huge brsports/shopping store withbr—see large indoor AQUARIUM withbrour local fish br—explore inside actual size replica of Ernest Hemingways BOAT the Pilarbr—eat and WATCH THE SUNSET at largest TIKI restaurant docksidebr—watch them FEED THE SHARKSbrnightly on the restaurant dockbr—dine more intimately upstairs at ZANE GREY LOUNGE with stunning SUNSET views on Florida BaybrbrTake winding footpath to next door Morada Bay Restaurant ON THE BEACH seating-known for unique tapas menubrbrCROSS the street to Florida keys Brewery-one of 3 breweries in Islamorada brbr—HANDS ON Diving Museumbrfull of diving history and artifactsbrbrFEED THE TARPON at Robbies brEAT ON their DOCK from wonderful menu itemsbrSHOP at the many local artists booths all around RobbiesbrA TRUE KEYS EXPERIENCEbrbrAnd soooo much more ONLY IN ISLAMORADA br

BEAUTIFUL ISLAMORADA KEYS HOME

Islamorada, Florida, United States

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Bath

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$440.48

Village of Islamorada Vacation Rental license #24-0372.br113 Anglers WaybrCall Jennifer for more information 305-240-0592. (2 houses side by side available)brThere is no other neighborhood like Anglers Reef in Islamorada. It's beautiful Key West style pastel colored homes inside resort community, with garden like flora and fauna such as bougainvillea meticulously maintained, with a fantastic oceanfront swimming pool and boat docks and views over the Atlantic Ocean that will take your breath away. Just minutes from many local shops, bars and restaurants. Access to the ocean does not get any easier than at Anglers Reef. When we first found Anglers Reef on vacation six years ago we were sold and never went anywhere else.brbr The Blue Marlin House:brbrThere Are 52 Homes at Angler's Reef With Only 36 Boat Slips. Our home has the option for you to bring your own boat and use the dock (additional cost) . It is a Safe, Gated Community with very little traffic, truly an oasis. Enjoy coffee or cocktail on one of four porches, (each bedroom upstairs has its own balcony and bathroom) Or enjoy the community Paddle Boards and Kayaks or just relax with a Netflix movie.brbrYou will tell you are someplace special when you see our 2-bedroom, 2.5-bathroom house, surrounded by wonderful landscaping, amazing palms, bougainvillea, and some of the most colorful tropical foliage that only the tropical Florida Keys can offer.brbrBlue Marlin's first floor offers a spacious, wide open layout with an over-sized sectional couch. Granite counter tops, all updated appliances, kitchen is stocked with pots and pans, utensils plates, everything you will need to prepare anything. Stay entertained during your downtime by watching your programming of choice on any of the home’s 3 flat screen TVs with hulu subscription, or surf the web via the complimentary wireless internet access. We also offer two bikes that you are available for you to ride.brbrbrThe second floor offers a spacious Primary Bedroom with comfortable King size bed and an en-suite bathroom. There is a balcony and a television for you to enjoy. brFull size washer and dryer is in the hallway for your convenience.brThe Guest bedroom has a brand new Queen over King BunkBed with new comfy mattresses (Jan 2024). This room also has an en-suite bathroom with bath tub and a TV and balcony.brbrChildren of all ages will love the pool and the fact that there is no road traffic, and the geckos will keep young kids entertained for hours!brbrThroughout your visit, you and your companions will get to enjoy outstanding recreational facilities at Angler’s Reef. These community amenities include a heated swimming pool with outdoor bathrooms, chaise lounge chairs and tables overlooking the breathtaking blue waters of the Atlantic Ocean, and boat slips available for rent. Look forward to soaking up the sun at either of the 2 private beaches, located just a few short steps away from every home that flank the marina. Also the world famous Islamorada sandbar and Alligator Reef are a short boat ride from the opening of the channel.brbrNext door is the Yellowtail House. For large parties or families both can be rented together, their layout is identical and both share high end furnishings. brbrA dock is available also for an additional cost.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.brbrTHE HOUSE JUST GOT A TOTAL INTERIOR REPAINT AND NEW FLOORING AND ITS BEAUTIFUL!

Anglers Reef Islamorada 2/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool

Islamorada, Florida, United States

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Bath

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$449.57

Come stay at the Tipsy Turtle in Angler's Reef! This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Angler's Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture. Quaint streets & walking paths wind through this village-styled retreat. 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 ($500/week). Or launch our kayaks and Paddleboards from the private beach (kayaks and paddle boards available for all guests to use). This home has 2 Master bedrooms located on the 2nd floor. The first bedroom has a King Sleepy's Curve Foam Mattress and the Second has another King Sleepy's Curve Foam Mattress. Each bedroom has a private bathroom and each having a private porch with an ocean view, and has 2 more porches downstairs with ocean views for morning coffee or cocktails. Upgraded Queen Sleeper Sofa downstairs sleeps 2 more . Homes decor includes stainless appliances, granite counters, Brazilian cherry hardwood floors, 3 flat screen TVs including Cable & WiFi. Check-in/Check-out days are Saturday. Message me should you wish to check in/out on a different day. Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrIslamorada is synonymous with the best fishing - gulf, backcountry or ocean. There are plenty of guides, charters or boat rentals. You can also try for hogfish, snapper, mahi, tuna, bonefish, tarpon, snook, & more. Right at the Anglers Reef docks you can catch mangrove snapper, ladyfish, jack crevalle, moonfish, grunts, mullet & barracuda depending on season. We had one lucky vacationer catch a 70 pound Tuna right off the docks.brbrFor those who don't like fishing there is still a ton to do which is one of the reasons we chose Anglers Reef. The development and the Islamorada area have a lot to do for people who are not into fishing. Just hanging at our home on one of the four porches is enough of a full day for some. brbrEnjoy our spacious decks with a book or cocktail and the views of the turquoise waters and ocean breeze. Or enjoy the large community pool (heated in winter and cooled in summer!). And if that's not enough you can take a stroll thru the community or relax on the private beaches or you can launch Kayaks and Paddle boards right off our beaches.brbrRestaurants: a short 5 minute walk are Hog Heaven, Smugglers Grill and the Island Grill. By car a few miles away are lots of oceanfront or bay front restaurants to eat at. All are amazing. See our recommendation book in the home.brbrAttractions: Swim with dolphins at Theater of the Sea 1/2 mile south. Founders Park is just a mile north with concerts and lots to do. The Islamorada Chamber of Commerce visitors center is also near the entrance to Founders Park for local info as well as affordable postcards, posters, T-shirts and books.brbrGrocery & Other Shopping: Publix just opened at MM83 on the Island and is just 2 miles south of the home. For quick items Trading Post is a little further south. There is also a Winn Dixie a few minutes north (around Mile Marker 91 in Tavernier. There is also a West Marine, Bass Pro Shops and other cool little stores around the town.brbrParks 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.brbr*The Eagle - This 287 ft ship was intentionally sunk in 110 ft of water as a dive attraction, cloaked in sponge & coral, populated by grunt, harpoon & jack. *Davis Reef - Reef revered for its incredible concentration of grunts & schoolmaster snapper, as well as several amiable resident green morays, long accustomed to benign interaction with the dive masters. *Alligator Reef - Now marked by a 136-ft-tall lighthouse, on this spot in 1822 the USS Alligator grounded & sank while protecting a convoy from pirates; remains of the wreck are the twin piles of ballast stones, but the coral reef - in just 25 ft of water - is vibrant and alive. *Conch Wall - Offering a precipitous sloping wall & captivating concentrations of barrel sponge & gorgonia punctuating seafloor. *Crocker Wall - A 450+-foot-long wall in 50 ft of water. The wall has a 30 ft decline and features grunts, yellow tail &grouper with spur-and-groove coral & block coral.brbr*Pickles Reef - Reef's minutia in 15-25 ft of water.

Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach

Islamorada, Florida, United States

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