Vacation Home Rentals By Owner In Islamorada, FL

Enjoy watching the ospreys and manatees from the dock at this beautiful Port Antigua home on Biscayne Blvd. You have access to a large private sandy beach with zero entry to waist deep water to sit and sun bathe and bring the kids for a splash. 4 beach cruiser bicycles are included for riding around the neighborhood. The dock has a large fish cleaning table and steps down into the clean water. Enjoy the breeze and the views from the downstairs covered entertaining area. No neighbors across the canal! This home has an elevator for easy access to the second floor (very handy for suitcases and large grocery orders) where you'll find 3 large bedrooms, 2 full baths and an open concept kitchen, dining and living area. An office/den with custom desk is located just off the kitchen if you need to get some work done. Washer and dryer available on the second floor. Downstairs there is a large den/entertainment area as well as 2 large bedrooms, including a pack and play for little ones, 1 full bath and a kitchenette with full size frig/freezer, coffeepot and microwave. Access the upstairs via outside steps, indoor circular staircase, or the elevator. The house has an outdoor ice machine and a separate bait freezer. Islamorada is the Sportfishing Capital of the World! Come and enjoy!br28 day minimum stay required.

Fabulous Island Getaway! Easy access to Florida Bay, Private Beach, Elevator

Islamorada, Florida, United States

Bed

Bath

Sleeps

$338.66

After a few years of construction, Morada Breeze , Venetian Shore's Waterfront Paradise is back and better than ever. Two Bedroom newly constructed lower level home awaits you in Venetian Shores, Islamorada's premiere community. Queen size bed in the main bedroom and in the second bedroom a daybed which converts to a king size bed. Washer/Dryer in the unit for your convenience. Fishing, snorkeling and sandbar within minutes from your dock via Snake Creek. Plenty of room for your boat and all your toys. Fishing station and a heater pool to relax after a long day fishing. INQUIRE ABOUT SEASONAL RENTAL DISCOUNTED RATES ! Come join us in the Florida Keys where fishing has never been better! Minimum Stay: 28 days. Before Requesting to Book please reach out to owner to confirm availability. Please note that you are renting the downstairs. Thank you.

SEASONAL WATERFRONT RENTAL in Venetian Shores, Islamorada, Pool & New Dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1951.55

It's an Ocean Oasis here on this beautiful estate in Islamorada! Over one acre right in front of your PRIVATE beach on the Atlantic Ocean. No one bothering your sandy shoreline while you bask in the sun. Enjoy 5 bedrooms, 4 bathrooms and countless amenities. Two kitchens, ample living rooms, & two sets of washers and dryers are just some of our conveniences. Make your way outside, and you will not be disappointed with the extensive choice of complimentary entertainment. A large pool surrounded by chaise loungers sits relatively near our 10-person hot tub. Here you can also find ample Adirondack chairs with side tables surrounding the area. If you're more the physical type, get ready to have some fun! Head over to your personal paddle bar where you can find various water toys such as kayaks and paddleboards. Let's not forget our outdoor toy closet; here you can find several cornhole sets, life jackets, and other outdoor games like giant Jenga. brbrAs the sun comes down, get ready to enjoy some of the most magical skies you will ever see. Our sunsets here are world famous and you won't want to miss this! May we suggest; this is the perfect time to let the grill master in your group do their best work! Always cleaned and ready to go, our grill sits just alongside our 10-person teak bar. Equipped with a built-in cooler and bar lights, it sets quite the tone for a relaxing seaside night. Easily a great way to enjoy the locals catch. Something found on almost every corner here in Islamorada!brbrThe night is young, and you have some pretty great options to still enjoy on this property. Our hammock cove is a place many find themselves happily lost. With more stars in sight than you've probably ever seen, it's easy to see why people migrate here. The swaying palm trees are a welcomed sound as they support 3 double hammocks for your enjoyment. Still not ready to rest you say Great!!! Grab one of the many beach towels on premise and head back to the pool. A completely surreal experience awaits here at night. The market lights & perfectly placed landscape lighting pair perfectly with your choice of tunes on our Sonos surround speakers.br If true relaxation is what you're looking for, then you've found the perfect place!br

Oceanfront Estate on Islamorada, Florida Keys - Ocean Oasis of Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$415.77

Escape to Islamorada’s Finest Oceanfront Gated Community brbrSoak up the sun and enjoy the ocean breeze from this charming 2 bedroom, 2 bath Key West style villa located in the exclusive community of Angler’s Reef. Accommodating up to six people, this exquisite home makes it easy to both entertain and relax with its open floor plan, private balconies, and abundance of on-site amenities. brbrOn the ground level of your island home, you will find a charming dining room, fully equipped kitchen, and spacious living area complete with a large sectional sofa, stainless steel appliances, bar seating, and a convenient half bath. No detail was left undone with granite countertops, hardwood floors and crown molding. French doors leading to a tranquil back porch with comfortable lounge furniture make this a perfect place to unwind with a pre-dinner cocktail or to dine alfresco. brbrUpstairs you will find two spacious master suites complete with private balconies, flat screen TV’s with Netflix capabilities, and clean ensuite bathrooms. The second floor also features laundry facilities and a futon for guest use. brbrFor your convenience, the home is equipped with complimentary WiFi, Netflix, beach towels hair dryers, pool floats, beach chairs, two 2 man kayaks, games, BBQ grill, coozies and whatever else you may need for the perfect Florida Keys Vacation.brbrThe grounds of this luxurious oceanfront resort are perfectly decorated with lush tropical landscaping and quaint streets filled with bright Caribbean-inspired homes. Enjoy all the wonders of this highly sought after community including a heated oceanfront pool, private marina with deep-water dockage and two white sandy beaches with kayaks for your own use. brbrLooking to explore further Perfectly located on the oceanside of Windley Key, you can hop in your boat easily access some of the best fishing spots in the Atlantic or launch a kayak from the beach and visit the world-famous Islamorada sandbar. brbrAnglers Reef is located at mile marker 84 and is one of the best kept secrets in the Florida Keys. You are only minutes away from downtown Islamorada or Tavernier with great restaurants, boutiques, grocery stores and local attractions. brbrPlease inquire for boat slip availability. brbr7 night minimum. Saturday to Saturday rentals are preferred. Please inquire for rates and availability.brbrAngler's Reef 105 ~ MM84.5 Oceanside brbrVR: 24-0236

Charming Angler's Reef Home with Pool, Dock, Beach & Ocean View

Islamorada, Florida, United States

Bed

Bath

Sleeps

$471.99

Bayview home located at the end of a canal on Airstream Lane on Plantation Key. This beautiful property offers peaceful waterfront living with incredible views of Florida Bay and some of the best sunsets in the Keys.brUpstairs features 3 bedrooms and 2 bathrooms, along with bright living spaces and windows that overlook the bay, creating a relaxing setting to enjoy the views and evening sunsets.brDownstairs includes a separate 1-bedroom, 1-bath guest space, offering additional privacy and flexibility for families or groups.brThe outdoor area is perfect for enjoying the island lifestyle, featuring dockage, a summer kitchen, seating areas to watch the sunset, and kayaks and bikes available for guests to enjoy. Whether you're heading out on the water or relaxing at the house, this property offers a great place to experience the laid-back Plantation Key lifestyle. If booking more than a year in advance current prices may not reflect the annual cost of living increase. Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us.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.

Charming 3-bedroom canal home in Islamorada with modern amenities for 6 guests.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$461.44

*3 Bedrooms, 2 Baths, Single Story Charming Keys House, Washer /dryer, Wifi/cable, backyard is completely fenced inbrbr*strategically Located Between Miami and Key West( 2hrs from Ft Lauderdale International Airport & 1.5 Hrs from Miamibrbr60 Foot of Dock With Electric & Water ; no fish cleaning stationbrEasy access to both Bay Side & Ocean BoatingbrAmple Side yard parkingbrThere are many places around to put your boat in... most of our guest use Caloosa Cove Marina (ocean side)brbr*Private (key Required) White Sand Beach (dogs are not allowed)br2-man Ocean Kayak, 3 Bicycles, the Hammock for Two & Enjoy the Night Sky Full of the Constellations for You to Namebrbr*close to Fine Dining & the Best Sport Fishing in the Keysbr, 1.5hrs from Key Westbrbr Islamorada, 33036, aka White Marlin Beach, aka Lower Matecombe ... aka MM 74.5brbr

Casa 157 @ White Marlin Beach

Islamorada, Florida, United States

Bed

Bath

Sleeps

$981.86

Introducing the Bonefish House, at Tarpon Point!brbrThis opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed and fully equipped chef’s kitchen offers the finest high-end appliances to satisfy everyone’s culinary needs. Whether you are cooking for two or eight, there is plenty of room for everyone to have a seat at the table. Or, eat al fresco right off the main level balcony and enjoy the balmy ocean breeze. The integrated Sonos system offers the ultimate wireless home sound system that streams off the house WiFi network and fills the home with brilliant sound. br brThis sought after gated community boasts beautifully landscaped grounds, oceanfront pool with heater and chiller, 420 feet of ocean frontage, an observation dock you can fish from, and a beach area where you can launch your paddle boards, kayaks or canoes. Indian Key State Park is just a paddle away!br brWake up to exquisite sunrises and ocean views right from the master bedroom, which offers its own private balcony for a birds eye view, a king size bed, a private en suite bath with double vanities, a separate shower and a soaking tub. There are two additional bedrooms upstairs, each equipped with king beds and en suites. There is an additional queen bedroom on the main level with a neighboring bathroom. Each bedroom has it's own flat screen smart TV with streaming service capabilities. br brLocated at mile marker 77.5, at the northern tip of Lower Matecumbe Key and conveniently located across the street is the world famous Robbies which offers fishing charters, snorkel charters, restaurants, shops, parasailing, kayaks / paddle board rentals. You can even hand feed the enormous tarpon! Downtown Islamorada is just 4 miles north which offers endless restaurants, breweries, shopping, activities and grocery.br brLove The Bonefish House at Tarpon Point but need dockage Robbies of Islamorada is located directly across the street from Tarpon Point and offers transient boat slip rentals. There is also Safe Harbor Islamorada Marina which is approximately 3.3 miles north and Caloosa Cove Marina which is approximately 3.7 miles south. Both offer transient boat slip rentals.br brWith our Coastal Concierge Service we can have your groceries and adult beverages chilling in the fridge prior to your arrival so you can settle straight into vacation mode. Just send us a list and we will take care of the rest! Yes, it’s that easy! br brBOOK TODAY before it's too late!br brHave 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.brbrIslamorada Vacation Rental License #: 26-0093

The Bonefish House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home

Islamorada, Florida, United States

4

Bed

4

Bath

8

Sleeps

$1040.1

This stunning, fully renovated retreat checks every box for the perfect Keys escape—sweeping bay views, a private pool and spa, and all the outdoor living space you could dream of. Soak up the sun from your two-story tiki, gather around the fire pit for sunset cocktails, or fire up the grill in the outdoor kitchen for a laid-back dinner under the stars.brbrStep inside to find a beautifully designed interior with coastal-chic finishes, spacious living areas, and water views from nearly every room. With dockage for your boat, you're just minutes from world-class fishing, snorkeling, and sandbar adventures.brbrWhether you're floating in the pool, reeling in the catch of the day, or simply relaxing with a drink in hand—this bayfront beauty delivers the ultimate Islamorada vacation experience.

Relax in Sunset Cottage, bayfront 4BR pool home retreat in picturesque Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$336.03

The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assigned boat slip in private marina just around the corner. All new kitchen, baths, porcelain tile flooring, fully furniture and LOTS more. Three bedrooms, two bath home on a peaceful plugged canal - in one of the Upper Keys' best neighborhoods. Immediate access to the bay from the private marina and very easy access to the ocean via Snake Creek. It is located in Islamorada minutes away from world class dinning and amenities' such as free access to all of Founder's Park just to name a few. Founder's park there is a convenient boat ramp and a beach. Your backyard is your playground in this location. Metal roof, impact windows/doors, concrete stilts. This home is an exclusive enclave giving you privacy to enjoy true Florida Keys lifestyle.

House in Islamorada, in exclusive Venetian Shores.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$354.76

This single-story canal front home located in the heart of Islamorada (MM86) in the Florida Keys-fishing capital of the world. Home is on the bayside in the upscale community of Venetian Shores. This spacious split floor plan home features 3 bedrooms and 2 bathrooms, open floor plan living area, screened in patio and large outdoor deck for your enjoyment. Home is equipped with all comforts of home.brEnjoy the canal view from almost every room in this immaculate home! Open floor plan includes the living room with quad-reclining sofa, a large screen TV, fully equipped kitchen, dining area and eat in counter with bar stools.brThe large master bedroom offers serene canal views with a king-sized bed, an over-sized en-suite bathroom which includes a jetted tub & separate shower. Bedrooms 2 and 3 both feature queen-sized beds with a shared bathroom. brRelax and enjoy your morning coffee or favorite cocktail in the private fully screened patio or enjoy sitting under the stars as you barbecue on the gas grill on the large outdoor deck all while enjoying a view of the canal surrounded by mangroves offering a tropical atmosphere. brOther amenities include high speed WIFI, smart TV’s and large washer and dryer.brThis home is centrally located where you will not have to go far to enjoy the best that Islamorada has to offer. Founders' Park is one mile north where you can enjoy access to many amenities such as: a sandy beach, Olympic-sized pool, walking and bicycle paths as well as volleyball, baseball and softball fields, basketball, tennis, soccer, doggie park, kids' playground, marina, boat ramp and much more. (Some additional fees may apply at Founder's Park). Nearby Snake Creek Marina offers boat slip, boat & kayak rentals. Fine dining restaurants such as Chef Michael’s, Ziggie Mad Dogs, Pierre’s, MM88 restaurants are nearby as well as casual dining restaurants such as Island Grill, Lorelei, Islamorada Fish Company and the historical Green Turtle Inn. brShopping is also conveniently nearby with grocery stores and many other retailers in proximity.brbrMINIMUM 28 DAYS RENTAL

Beautiful, Spacious, Single Story Home - Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$384.64

Sleeps 8, 2 Story Townhome On The Bayside, Mile Marker 87brbrOur Islamorada beach modern decorated townhome is waiting for you. It’s a two story unit and third level loft; 2 Bedroom/2 Bath - sleeps 8.brbrNext door is Founders Park & Plantation Yacht Harbor.brbrA private gated community with 24hr security. The grounds have 2 tennis courts, swimming pool, club house, private beach, boat slips and fishing dock.brbrbrCome and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World.brbrThe World Famous Tiki Bar is less than 5 minutes away – Holiday Isle/Post Card Inn, 'Best Rum Runners in town.' Numerous boat charters located within 5 minutes, 'this is the fishing capital! Water Activities; Jet Ski and boat rental at Post Card Inn for accessing the famous sandbar.brbrYou will be just minutes away from a large chain grocery store, CVS pharmacy and movie theater. Multiple choices for fine dining and casual dining within 5-10 minutes.brbrbr*House cleaning procedures conform to the new enhanced standards issued by the American Hotel & Lodging Association (AHLA.com) and the CDC*.brbrbrPer guidelines, the unit will only be rented once every 28 days. You can book a shorter stay however unit will be blocked for 28 days. br* for additional information or other flexible dates, contact us brbrbrWe also use other sources to book a reservation. If you are looking for more specific dates, contact us with any questions prior to booking online.

Paradise @ Islamorada

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$248.38

PROPERTY NAME: The Bungalow Housebr32 Park Rd Islamorada, FloridabrbrLocation: Bayside Very close to the Publix Shopping CenterbrbrMINIMUM: 28 Days, All stays must be the whole month (s), No Partial Months AllowedbrbrMile Marker : 82brbrDetails: This home is absolutely beautiful with your own pool and Tranquil backyard - Bayside walking or biking distance to Downtown. The property is Private, plenty of parking for your vehicles and boat trailer if needed. It features a beautiful pool that is heated in the winter and chilled in the summer When you walk in you are at home, the house is beautifully decorated. The living room has a faux fire place and plenty of seating for the family, the kitchen is completely remodeled and fully stocked with everything you may need for your stay. You have 2 bedrooms and 2 baths there is a 3rd room that has a single pull out bed, with a desk and chair. There is a front porch to sit and enjoy the beautiful surrounding lush trees. You also have a Porch in the backyard to sit and enjoy the pool area. The backyard features beautiful trees and shrubs for privacy while enjoying the Pool. If you are looking for Private and Quiet, this is the house.brbrSleeping Arrangements: Sleeps 5 comfortablybrPrimary Bedroom: King Bed that is adjustablebrGuest Room: Queen BedbrbrAmenities Include: Heated Pool, Outdoor Seating, BBQ Grill, Private BackyardbrbrActivities: Beach, Swimming, Boating, Offshore Fishing, On shore fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours

Beautiful Pool home in Islamorada

Islamorada, Florida, United States

3

Bed

Bath

6

Sleeps

$691.09

PROPERTY NAME: Casa Marbr115 Ponce de Leon Blvd, Islamorada, FloridabrbrLOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Port AntiguabrbrMINIMUM STAY: 28 DaysbrbrMILE MARKER: 74.5brDETAILS:Stunning two-story, 3-bedroom resort-style, professionally decorated home. Inside, you'll find a modern and welcoming home with tiled floors, comfortable furniture, and lots of attractive décor and personal touches.br brThe beautiful, modern kitchen has stainless steel appliances. The center island is great to prepare wonderful meals. The incredible kitchen is fully equipped and has a fabulous view out the window. Enjoy your meals at the dining room table with seating for six with gorgeous water views.br brThe three large bedrooms are all furnished with king-size beds. The main suite has a large walk-in shower and a separate jetted tub. Want to sleep in late The main suite has black-out curtains! Relax and enjoy the canal view while sipping your morning coffee or tea from the main bedroom's screened-in balcony.br brWalk out to your tropical paradise. The home is professionally landscaped providing privacy for your enjoyment while relaxing in the lounging area. An outdoor shower, with hot and cold water, is available for rinsing off upon return from the beach or just to cool off and refresh. You can take a walk along the private beach and enjoy a dip in the calm, clear waters. The beach has several chickee huts with charcoal grills for the enjoyment of beachgoers.br brThis is the perfect Keys home located in the heart of Islamorada in the sought-after Port Antigua community close to all kinds of fun activities like swimming, snorkeling, fishing, restaurants, and bars and with access to a beautiful, homeowner's private beach. No children under the age 12 and No smoking on PropertybrbrSLEEPING ARRANGEMENTS: Sleeps 6 comfortablybrPrimary Bedroom: King Bed Private Bathroom with Shower and Whirlpool Tub/Double VanitybrGuest Bedroom: King Bed Shared Bathroom with Shower/Tub Combo/Single VanitybrGuest Bedroom: King Bed Shared Bathroom with Shower/Single VanitybrbrAMENITIES INCLUDE: This home features dockage on a wide, deep-water canal. It can accommodate boats with maximum length of 24 Feet and a 5 foot draft. For your convenience, there is Wi-Fi, a washer and dryer. Gas BBQ Grill and an Enclosed outdoor shower with hot water,brACTIVITIES: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures. If you run out of things to do, Miami is only 83 miles away. brENHANCED 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.

Beautiful Pool Home located in Port Antigua

Islamorada, Florida, United States

Bed

Bath

Sleeps

$393.97

Enjoy peaceful Keys living at this charming bayside home located at Mile Marker 75 in Lower Matecumbe, the quiet south end of Islamorada. Set in a tranquil neighborhood, this property offers stunning sunset views and a relaxed island atmosphere perfect for a laid-back getaway.brbrOut back, you'll find a small private beach area surrounded by palm trees, creating a secluded space to unwind and enjoy the bay. The screened porch is the perfect place to take in the colorful evening sunsets, complete with comfortable tables and chairs for outdoor dining or relaxing.brbrFor even better views, head up to the roof deck where you can take in panoramic sights of both the bay and ocean sides of the island.brbrInside, the home features a comfortable layout with bedrooms located on opposite sides of the house and the living and common areas in between—offering both privacy and space to gather. Amenities include a flat-screen TV in the living room, cable television, and Wi-Fi.brbrWhile dockage is not available at this property, Anne's Beach is located just down the road. This beautiful natural area offers boardwalk trails, picnic and BBQ spots, and sandy areas tucked within the mangroves—perfect for a day by the water.brbrVacation Rental License: VR-041brbrIf booking more than a year in advance, current rates may not reflect future cost-of-living adjustments. Many of our guests return year after year to enjoy this special property. Reservations are not confirmed until you speak directly 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 2-bedroom retreat in Islamorada with stunning open water views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$2328.24

Summary:brbrExperience Unparalleled Luxury at Pineapple Beach: Your Dream Getaway Awaits! Indulge in a 5-Bedroom Haven with Private Dock, Oceanfront Pool, and Endless Amenities on 3 Acres in Islamorada.brbrbrbrThe Space:brbrPineapple Beach – Private Oceanfront Estate in IslamoradabrbrbrbrPineapple Beach is situated on more than 3 acres in the central area of Islamorada. This exclusive 5-bedroom luxury residence is the embodiment of your dreams, offering nightly bonfires, a challenging putting green, a cabana bar, a private dock, and numerous other amenities. Get ready to pack your bags and experience a vacation that will leave an indelible mark!brbrbrbrIf you’ve ever envisioned lounging by your own private oceanfront pool, gazing over a small beach and expansive ocean views, your dream is about to come true. This secluded, gated estate offers an unmatched level of privacy and space rarely found in the Florida Keys.brbrbrbrInside, the home features a gourmet kitchen and a dining area that accommodates 10 guests, offering breathtaking views of the water. With three levels, there’s ample space for everyone to relax and unwind. Settle into the living room for movie nights on the 65” TV or challenge friends and family to a friendly foosball game.brbrbrbrOutdoors, indulge in your own small private beach area, complete with a fire pit, boat dock, heated pool with spa, pool bar, golf green, and abundant seating to take in the serene coastal surroundings. While the shoreline is maintained regularly, guests should note that seasonal winds and tides can bring natural sargassum seaweed to the beach. This is a normal and expected part of the coastal environment; although it is cleared periodically, it is not possible or environmentally appropriate to remove it continuously.brbrbrbrThe main kitchen includes a full-size refrigerator, wine cooler, ice maker, two dishwashers, microwave, stove, Keurig, dual ovens, mini fridge, toaster oven, coffee maker, blender, and a 35” TV.brbrbrbrExterior Amenities:brbrPrivate dock accommodating boats up to 32 feet (max draft: 36 inches, width: 12 feet)brbrHeated pool and spabrbrPool bar and shaded seating areabrbrOutdoor showerbrbrFire pitbrbrFoosball table, cornhole, basketball hoopbrbrHammocksbrbrDedicated golf greenbrbr213-foot private beach with convenient water entrybrbr2 kayaks and 2 paddleboards with easy launch accessbrbrAmple parking for multiple vehicles and/or boat trailerbrbrBooking PoliciesbrbrbrbrMinimum Stay:brbrA 7-night minimum stay is required by city regulations, with no exceptions. The city determines the maximum occupancy, and it cannot be exceeded (including adults, children, and infants).brbrbrbrCancellation Policy:brbrWe maintain a strict 60-day cancellation policy. If the cancellation is made at least 60 days before arrival, you can receive a full refund (excluding processing and admin fees). If you cancel within 60 days and we are able to rebook the same dates, you will receive a full refund minus processing and admin fees. If we are unable to secure another booking, only the deposit will be refunded.brbrbrbrContract:brbrUpon confirmation of your booking, you will receive an Adobe E-Sign contract for signature, which will be automatically returned to us once signed.brbrbrbrPayment Options:brbrThe total reservation charges include credit card processing fees by default. We gladly accept checks or EFT payments with no additional fees, and in that case, the processing fees can be removed. Credit card payments are subject to the following fees:brbr– Visa, MasterCard, Discover: 3.5% processing fee (excluding taxes and deposit)brbr– American Express: Additional 0.99% fee (excluding taxes and deposit)brbrbrbrGuest Access:brbrPrivate gated entrance, elevatorbrbrbrbrThe Neighborhood:brbrLocated in a secluded area of IslamoradabrbrbrbrGetting Around:brbrThis home is about a 10 minute drive to the grocery store.brbrbrbrInteraction with Guests:brbrCheck-in is private and self-guided. We won’t be there in person, but we’re available 24/7—call or text us anytime if any issues come up

Pineapple Beach

Islamorada, Florida, United States

Bed

Bath

Sleeps

$2115.86

Set on nearly three private acres with 200 feet of secluded Atlantic shoreline, The Oasis is a truly rare Islamorada estate offering space, privacy, and one of the most unique features in the Florida Keys — a heated saltwater pool positioned directly on the ocean itself.brbrThis exclusive compound consists of two separate homes, thoughtfully designed for comfort and flexibility. The main residence offers one bedroom and 1.5 baths, while the guest house features two bedrooms and one bath. Each home includes its own kitchen and living area, allowing families or groups to gather together while still enjoying private space when desired.brbrThe grounds are expansive and beautifully maintained, framed by towering palms and open water views in every direction. Spend your days launching one of the four kayaks or two paddleboards from your private beach, cruising the neighborhood on one of six bicycles, or enjoying a game of bocce ball or cornhole as the ocean breeze rolls in.brbrModern comforts are seamlessly integrated throughout, including enterprise-grade high-speed Wi-Fi, a Tesla charging station, professional mosquito control service, five 50” smart TVs, and stainless steel appliances.brbrPet friendly and ideally located in the heart of Upper Matecumbe — just 0.7 miles from Publix and minutes from Islamorada's best dining, marinas, and sandbars — The Oasis delivers something exceptionally hard to find in the Keys: acreage, beachfront, an oceanfront pool, and total privacy, all in the center of town.brbrIf booking more than a year in advance current prices may not reflect 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. brVACATION RENTAL LICENSE: 24-0120 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.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.

Discover 'The Oasis': a stunning 3-bedroom retreat in Islamorada with a heated private pool.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$259.98

Come and stay in our 3 1/2 bedroom getaway by the scenic bay in breathtaking Islamorada. * Enjoy your community's private white sandy beach, you’ll find sparkling turquoise water and waving palms that make for a genuine island haven. * Immerse yourself in the laid-back island lifestyle in our soothing new heated pool or get active by swimming, kayaking, snorkeling, or pier fishing in our bay. Venture next door to Founders Park for another sandy beach and many fun activities. brRemote Work & Online Fun:* Stay connected with our free fastest fiber optic WiFi. Two office areas. Dual monitors ready to connect.brExtra Conveniences:* Lots of extra conveniences such as a large washing machine and dryer. * Unwind in the cozy living room or indulge in a movie night with the smart TV and extra channels. * The open floor plan makes it a great space to sit with your family and friends while others are preparing food in the kitchen or on BBQ.* Yes. The fully stocked kitchen, complete with a BBQ grill, allows you to savor delicious home-cooked meals. Dine on a large family table or step outside to dine on our patio. brThis vacation home offers endless opportunities for fun and relaxation. Whether you're seeking a family getaway or a romantic escape, this beachfront oasis in Islamorada is the perfect destination to create lasting memories.brSleeping Logistics / Bedrooms:br* Master bedroom has a dreamy king bed with an awesome mattress. * 2nd bedroom has another comfortable king bed with backyard views. * 3rd semi-private (open) area has a daybed and trundle bed. Best for kids. * 4th semi-private space is the loft, which has 2 twin beds. * Plus, the living room has a pull-out queen sofa-bed.brAs you can see, there are plenty of beds and space for everyone to sleep, relax, and enjoy the escape to paradise.brbrNo waiting for bathrooms as we have Two full bathrooms (downstairs and upstairs).br***** IMPORTANT: All guests must be pre-registered and agree to original guest count requested.*****br* Nice bedding & towels. * Best community for fun activities! We offer a few as is bikes, kayaks, and many more amenities. brAwesome location in Islamorada. We're only a short walk to restaurants and shopping. Plus, we have excellent 24-hour / 7 days per week onsite security. brbr* The number of guests staying or visiting must be agreed upon during the booking. Adding more guests than accepted will mean you are cancelling your reservation. You will be asked to leave. brbr* Unregistered guests or would be day visitors are NOT allowed into the community without the owner’s prior authorization. brbr* We have a spiral staircase. Both bedrooms and one office are on the 2nd floor via the spiral staircase. brbr* There is also a ladder/stairway to get to the loft, so ladder and loft are not for small children or toddlers. The loft has a lower ceiling. brbr* Renters are NOT to dock at the EBC Dock. Renters can do pick-up and drop-off. There are nearby places that provide slip rentals, such as next door at Founders Park. (I can provide a full list.)brbr* Pets are NOT allowed as we suffer from severe allergies. brbr* We do NOT accept parties in our home. Best to consider another property. brbr* We have a few extras (like old bikes and kayaks) in as is condition. Use these at your own risk. Be careful on the water and riding bikes. Please always apply and follow water and roadway safety rules.brbr* A free guest passes may be available for driving into Founders Park. Please give me a heads up to make a request for you.brAsk any question.Jose GoToKeys

Amazing Sandy Beach Sunsets + New Pool + Best Location w/ Park - Bikes & Kayaks

Islamorada, Florida, United States

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Bath

Sleeps

$571.87

''BEAUTIFUL BAY-FRONT PROPERTY!!!!'' NEW POOL Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath.brEntire house has been remodeled, fully furnished, with a 90 ft Dock. Bring your clothes, boat, fishing and dive gear. Located in desirable Islamorada where you will have easy access to some of the best back-country fishing, and or ocean fishing which would include all of the paddle boarding, snorkeling, and diving that anyone would ever want, just minutes from Channel 5 and channel 2. Dog beach is 3 min away by boat. You will love the back porch outdoor living space which includes your own Bar over looking the water. This is a Boating, Fishing Scuba Diving/Snorkeling Paradise.brbrHouse, 3 Bedrooms, 2 Baths, Sleeps 10brbr213 Tollgate Blvd., Islamorada, Florida Keys mile marker 73 bay side, located 88 miles south of Miami International Airport and 71 miles North of Key West. It has three bedrooms, two bath, private home totally remodeled in late 2019, 90 foot dock, bay side with easy access to ocean.brbrFeatures: washer, dryer, gas BBQ, charcoal BBQ, hammock, ice freezer, ice maker, Outside Bar, fish cleaning table, tropical foliage, TV in living room, DVD, laminate floors, nautical ceiling fans throughout, central air conditioning, wireless high speed internet, all the amenities and conveniences of home in this one of a kind rental in the fabulous Florida Keys.brbrNo smoking inside the house please.brbrI purchased this house after renting in the Keys for many years, I got tired of looking so hard for good quality, clean hotels to rent which were and are still very difficult to find. If you are looking for something 'nice' that the actual house looks 'better' than the pictures, that will provide for your family and friends a vacation where memories will be made, that will last a lifetime and that is clean inside-out, then this is your rental.brbrFor further information or questions, contact owner manager ,brbrUnique BenefitsbrbrThis is my only vacation house , I live only 2 hours away and I take care of the house as good as our main home. brbrThis is my Happy Place, Piece of Paradise and I use the house personally when it isn't being rented, I spare no expense to keep it up and maintain it.brbrWhy die hard fishing and diving people love it-brIt is on the Bay, very close ocean access. brbrArea Information:brbrIslamorada is the sport fishing capital of the world. I am located in Tollgate Shores subdivision on the bay-side.brbrAttractions Within a Short Distance:brbrAnne's beach is just south if of us the ocean side, it is a public beach where you usually find a lot of wind surfers.brbrMobil grocery store and cafeteria is just north of the entrance of our subdivision and it is a local for purchasing certain groceries and food, very convenient.brbrFavorite Places To Eat:brbrHabanos , Cuban restaurant and Caloosa Cove marina Oceanside just across from my subdivision. brbrRobbie's, eat outside by the water or inside, local place very typical of Keys.brbrLazy Days, 3 miles north next to Bud and Mary's marina. Lunch and dinner, great local favorite place, large portions always good food and fresh fish. Reasonable prices. sit outside or inside. Terrific when there is a full moon coming up on the ocean side.brbrGreen Turtle, north on the ocean side, sit inside, nice elegant restaurant excellent. Breakfast, lunch and dinner.brbrMidway Café, north, breakfast and lunch favorite. Great coffee , pastries etc.brbrChef Michael, north, dinner, excellent, nice, fresh fish, quality.brbrMangrove Mike's , north, local favorite for breakfast, very Keys oriented. Serves lunch too. Not fancy.brbrZiggie & Mad Dogs, north, real nice dinner restaurant, steaks and seafood, quality, nice ambiance.brbrBayside Gourmet, north, great lunch and dinner, not fancy, but great food and reasonable, family style. brbrSquare Grouper, north on the bayside in Islamorada marina. Excellent, my favorite for dinner.

A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$379.72

PROPERTY NAME: West Plaza br63 West Plaza Del Lago, Islamorada, FLbrbrLOCATION: Bayside HousebrbrMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedbrbrMILE MARKER: 74.5brbrDETAILS: West Plaza Del Lago will steal your breath away the moment you pull into the drive way. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter the home there is a charming foyer which leads to the spacious open concept living area with vaulted ceilings. On the right the kitchen, straight ahead the dining area and on the left the living area with a L shaped sofa. The fully equipped kitchen features stainless steel appliances and two breakfast/snack bars for casual dining - one by the sink area with bar stools and one with pull out saddle benches tucked under the granite counter top peninsula. For more formal dining there is a table which comfortably seats 6 people. In the living area a large wall mounted flat screen TV for your TV viewing pleasure. The two bedrooms are located just off the living area - one on the west side of the house and one on the east side - both have a wall mounted flat screen TV. The master suite has a king bed and ensuite bath with gorgeous tiled bath and large stall shower. The guest bedroom offers sleeping accommodation for three with two twin beds and a trundle. A full bath with tub/shower combination is adjacent. In addition to all the appealing features of this home there is an amazing sun room with a wall of windows overlooking the back yard, dock and canal. brbrOutside there is a 60' dock with boat lift and a fish cleaning station with water and electricity. The lift will accommodate a fully loaded boat up to 12,000 pounds. There is no additional charge for use of the boat lift, however adjustments to the bunks will be at guest expense by the company that services the lift. There is a table and chairs for relaxing outside along with three kayaks for your use - two singles and one double. Guest will have use of the garage for storing toys and use of the two freezers - one for bait only and one for food. There is a separate laundry area with a full sized washer and dryer. Wi-Fi is included. There's a gorgeous private sandy beach available only to residents of the Port Antigua neighborhood. The private sandy beach located directly on the bay offers oasis areas with BBQ grills and swaying palm trees. Bring your chair or blanket and enjoy the gentle tropical breezes. This is your opportunity to spend time in the Keys. Call or email immediately to make your reservations. This property is professionally managed by Keys Holiday Rentals. brbrSleeping Arrangements: Sleeps 5 comfortablybrPrimary Bedroom: King, Ensuite Shower/ Tub CombobrGuest Bedroom: 2 Twins + Trundle, Shower/ Tub CombobrbrAmenities Include: Dockage for up to a 35ft boat, kayaks, outdoor seating, BBQ grill. Sunroom seatingbrbrActivities: 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.

Beautifully remodeled roomy single family stilt home,

Islamorada, Florida, United States

Bed