Vacation Condo Rentals By Owner In Islamorada, FL

$362.26

Relax at Ocean Harbour K-35, a 3-bedroom oceanfront condo with dockage

Islamorada, Florida, United States

Ocean Harbour K-35 - This newly renovated unit is located in Ocean Harbor, one of the most exclusive condominiums in Islamorada! Enjoy this beautifully furnished three-bedroom, two-bathroom unit with endless views overlooking ocean. This 12-acre property is truly an island paradise, complete with tropical landscaping, heated pool, beach, marina, tennis courts, clubhouse, fitness room and much more. The rental includes a 30' slip in the on-site protected marina, complete with water and shore power, fish-cleaning stations, boat ramp and barbecue grills to cook your fresh catch. brIf 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. 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.

3

Bed

2

Bath

6

Sleeps

$899.03

/ Nightly

Condo

Beautifully decorated 3-bedroom condo in Islamorada, steps from the pool with beautiful views!

Islamorada, Florida, United States

Maison Matecumbe #301 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centrally located right in the heart of Islamorada within walking and biking distance to many restaurants, cafes, shopping, marinas and Islamorada's Art District. The unit has been totally renovated and won't fail to impress! Newly renovated swimming pool and hot tub to spend your days lounging along with Maison's beach, outdoor kitchen, tiki hut and spa.brIf booking more than a year in advance current prices may not reflect annual cost of living increase. brVacation Rental License # 24-3147brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Bed

Bath

Sleeps

$470.0

/ Nightly

Private Vacation Home

BRAND NEW Island-design home located in Islamorada fishing capital of the world!

Islamorada, Florida, United States

The Pink Sands House is located in the beautiful Lower Matecumbe island in close proximity to all your Class-A shopping, dining, and fishing needs. br The Island-Design House is located in a quiet, private community with your own private gated sandy beach area with sunset views and crystal clear warm waters. For area info call or text Alexis at (305) 345-7217. Also, per month COMPLIMENTARY HOUSE CLEANING will be occur for rentals 2 or more months. br Please note prices are subject to change based on season, holidays, occupancy, and weekly rates. br

Bed

Bath

Sleeps

$464.63

/ Nightly

Apartment

Breathtaking ocean views for your Paradise vacations

Islamorada, Florida, United States

Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house sanitized when one guest leaves and another enters. We take pride in having our home immaculate and now we are taking extreme measures to have our guests feel safe during their stay. brbrThis upstairs portion of a dual family fully renovated home with two bedrooms and two baths will comfortably sleep eight to provide you a dream vacation you will never forget!! brFully stocked new kitchen with granite counter tops and a huge island for entertaining and feeding your whole family comfortably. brAll new stainless steel appliances and new plates,cutlery,utensils,and glasses.brLiving room has two queen sleeper sofas and new 60 in smart TV.brIn hallway closet it has new washer and dryer for your conviniance during your stay.brTwo master bedrooms with new queen beds and each has their private baths. Each bedroom has a 42 inch smart TV.brEverywhere your walk in the house you will have a spectacular view of the ocean!!!brThis property also provides you own private dock and ramp for your conviniance with no extra fees. Our shed provides extra fenders to protect boats, brush and soap, electricity and water by dock, and a small freezer for bait and ice. For more outdoor fun you will be able to use the four kayaks and four bicycles provided to explore the ocean and sight see.brbrThose who want to charter a fishing captain upon request please contact Captain Avila 305-495-3322.

Bed

Bath

Sleeps

$450.8

/ Nightly

Condo

Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,

Islamorada, Florida, United States

“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much more. brbrThis 2 Bedroom condo at Bay Harbour sleeps 4 adults & two children 6 and under. Easy access to the Gulf or Ocean makes this the perfect home port for any fishing vacation. Bring your own boat or rent from any of the many boat rental companies in the area. If your vacation is more about relaxation, then kick back at one of the near-by beautiful sandy beaches. brNested within the gated community of Bay Harbour luxury condominiums, this unit will provide the ultimate base camp for the family to wind down after a day of fishing.br brTwo large bedrooms with private bathrooms plus a sleeper-sofa with half bath can accommodate a family of six or two couples very comfortably. The living room has brand new island style furniture and a 65” LCD TV for those movie nights or football watching days! brbrThe chef’s kitchen comes stocked with microwave, toaster, blender, coffee maker, crock pot, and even a vacuum-sealer for taking the fresh catch home. Fully stocked, you will enjoy your home prepared meals using new dishes, flatware, knives, pots and pans. And when you run out of clean clothes, launder them in the washer / dryer just off the kitchen. brbrThe master bedroom enjoys the same spectacular ocean view as the living room. Open the large sliding glass door to the screened in lanai and enjoy the fresh ocean breeze. A very comfortable king size bed and 45” LCD will make your nights very comfortable. Off the master bedroom is a custom master bath with Jacuzzi tub, walk-in shower and double sink. brbrThe second bedroom is perfect for another couple or children. Two twin beds, a 42” LCD and a full bathroom make it very private and comfortable. brbrLocated within view from the unit, you have access to a protected boat slip with power and water. The location of this condo is perfect for boating. Easy access to the gulf and ocean make it ideal for back country or open water fishing or cruising. The harbor is also very well protected from wind making docking easy. brbrThe amenities at Bay Harbour are plentiful. Lighted tennis courts, fitness center, BBQ grills, club house, and a large pool / hot tub provide many activities during your stay. You will also find a full assortment of beach chairs, tennis rackets, kids toys, water floaters, etc. for your personal pleasure. brbrLocated in Lower Metecumbe Islamorada, the area offers many activities including boating, fishing, sandy beaches, restaurants, shopping, and area tours. brbrbrbrbr

Bed

Bath

Sleeps

$435.0

/ Nightly

Villa

Oversized Islamorada Villa 110 in Gated Anglers Reef: Pool, Kayaks, Bikes, Beach

Islamorada, Florida, United States

Welcome to Villa #110, your perfect getaway! Nestled in the heart of Islamorada, this spacious 2-bedroom villa - one of the largest 2 BR units in the community - offers the ideal blend of comfort and tranquility for your tropical escape. Recently taken under new ownership, the villa is undergoing thoughtful updates to enhance your stay while preserving its laid-back island charm. brbrThis magnificent free standing home is located in Islamorada at Mile Marker 85 in the exclusive gated community of Anglers Reef, a quiet oceanfront community in the Florida Keys. Anglers 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 resort-like community pool overlooking the Atlantic Ocean, private marina (boat slip can be requested at additional charge) and 500 ft of private beach. Community owned kayaks and paddleboards are available for all guests to use.brbrThis home away from home will meet all of your needs! The villa offers 2 large Master bedrooms located on the 2nd floor. The first bedroom has a king size bed with a private balcony and the second oversized bedroom has two queen size beds with twin size pull-out trundle. Each bedroom has a private en suite bathroom. Plenty of room and privacy to unwind, and the perfect set up for those traveling with children. A rear deck with dining table, new Weber barbeque grill and lavish landscaping allow for restful downtime. Home decor includes stainless appliances, dishwasher, granite counters, hardwood floors, 3 flat screen TVs with premium cable and Wi-Fi. Rental includes all kitchen needs, dishes, glasses, pot/pans, etc. as well as linens / towels / beach towels and a BRAND NEW LG Washer/Dryer to set you up for the perfect vacation getaway! Two bicycles are included in the rental. A dedicated driveway with carport accommodates two vehicles.brbrIslamorada is universally known as the “Fishing Capital of the World” and provides amazing fishing opportunities - gulf, backcountry or ocean. Or fish off one of the picturesque Florida Keys bridges! Fishing guides, charters and boat rentals are easily accessible. Fishing is also permitted off our private dock.brbrFor the landlubbers, Anglers Reef offers many opportunities to relax. Enjoy our outdoor deck spaces with a book or cocktail. Swim and sunbathe at our large community pool (heated in winter and cooled in summer!). Or stroll through the community or relax on the private beaches. Something for all!brbrWithin walking distance are Hog Heaven, Smugglers Grill, the Island Grill, Three Rivers Resort Tiki Bar and Starbucks (one of three between Miami and Key West!). There are countless amazing dining opportunities in the Islamorada area.brbrFor recreation, you can swim with dolphins at Theater of the Seas 1/2 mile south or visit Founders Park one mile to the North to swim in the Olympic size swimming pool, use the diving boards, play tennis/pickleball or enjoy their shallow sandy beach. Charter boat tours readily available to visit the Sandbar, tour the area, scuba or snorkel. A short 30-minute drive to the John Pennekamp Coral Reef State Park in Key Largo for amazing snorkeling or to visit the famous Christ of the Deep Statute. The opportunities are endless!brbrPreferred check-in/check-out days are Saturday. Message us if 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!'brbrNOTE THAT THERE IS CURRENTLY A VRBO GLITCH WITH SOME OF OUR CHECK IN SATURDAY DATES (6/27, 7/4, 7/18, 12/5, 12/12, 12/19/26 AND 1/9, 1/16, 3/20, 3/27/27). WE ARE WORKING WITH VRBO TO CORRECT THIS TECHNICAL ISSUE. IF YOU ARE LOOKING TO CHECK IN ON ANY OF THESE SATURDAYS, PLEASE MESSAGE US. SORRY FOR THE INCONVENIENCE! brbrTIP: Look for discounts on Retail Me Not and Rakuten for your VRBO booking :) brbrWe look forward to welcoming you to our home away from home in the Florida Keys!

2

Bed

2

Bath

6

Sleeps

$383.7

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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.

Bed

Bath

Sleeps

$338.66

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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.

Bed

Bath

Sleeps

$278.98

/ Nightly

Condo

Discover the Charm of Island Living

Islamorada, Florida, United States

Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 4 people. Stay in touch with family & friends with free wireless internet. The master bedroom has a king size bed with two twin beds in the 2nd bedroom. If your children are small, we have a hi chair and various toys, Cd's and games. Our condo has a newly renovated kitchen with quart countertops, stove, dishwasher, microwave, coffee maker, blender & breakfast bar. brAll linens & utensils are provided. There is a separate dining room that seats 5 people. brVacation Rental License #VR-25-0316br brbrAmenities:brHeated Pool, Beach, Tennis Courts - Lighted, Pickleball Courts, Basketball & Volleyball Courts, Boat Dockage (Advance Request), Boat Ramp, Private Balcony, Central Air Conditioning, Laundry Facilities on each floor, 2 Roku HD TV's with Live Streaming. Wireless Internet, CD & DVD Player, Beach Cooler, Beach Inflatable's & Beach Chairs, Hair Dryer, Iron & Ironing Board, Board Games & Toys, Port-a-Crib, Hi Chair available.brbrActivities: brSwim with the Dolphins, Theatre of the Sea, Dolphins Plus, Dolphin Therapy. Dolphin Cove, Dolphin Kids, Powerboat Rentals: Robbies Marina, Tavernier Creek Marina, Island Boat Rentals. Sailboat Rentals: Treasure Harbor Marine. Back Country Fishing: Deep Sea Fishing: Whale Harbor Marina, Bud & Mary's, Holiday Isle. Diving & Snorkeling: Cheeca Lodge, Pennekamp State Park. Recreation: Skateboard Park, Hi Dive / Lap Pool. Nature: Wild Bird Sanctuary, Robbies-Tarpon Feed. Area: The Village of Islamorada has something for everyone. Any activity involving the Sea is easily accessible to our visitors, whether it is Snorkeling, Boating, Fishing, Diving, Water Skiing, Parasailing.brbrThe area offers a wide array of local artisan shops and boutiques. The restaurants are diversified, from many gourmet restaurants to fun dockside dining within a 10 mile area.brbrKeywords: Condo

Bed

Bath

Sleeps

$1951.55

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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

Bed

Bath

Sleeps

$415.77

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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

Bed

Bath

Sleeps

$471.99

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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.

Bed

Bath

Sleeps

$365.63

/ Nightly

House Boat

Aqualodge: 2-bedroom house boat with AC in Islamorada

Islamorada, Florida, United States

Your Islamorada adventure begins at this 2-bedroom house boat. Step aboard and enjoy a serene escape surrounded by cool waters and gentle breezes. The house boat features two full beds and a comfortable bathroom, making it a wonderful spot to relax after a day of exploring. Guests can unwind in a cozy, inviting space that feels like a home away from home. Whether you're here for a quick getaway or an extended stay, this unique retreat offers a peaceful setting to recharge. We're happy to assist with any questions while you stay at our house boat.

Bed

Bath

Sleeps

$981.86

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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

4

Bed

4

Bath

8

Sleeps

$1040.1

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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.

Bed

Bath

Sleeps

$461.44

/ Nightly

Private Vacation Home

Casa 157 @ White Marlin Beach

Islamorada, Florida, United States

*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

Bed

Bath

Sleeps

$336.03

/ Nightly

Private Vacation Home

House in Islamorada, in exclusive Venetian Shores.

Islamorada, Florida, United States

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.

Bed

Bath

Sleeps

$413.55

/ Nightly

Condo

Beautiful 'Keysey' Condo in Bay Harbour Gated Community 26-0169

Islamorada, Florida, United States

Enjoy the spirit of the Florida Keys in this 'keysey' furnished condo with everything provided. All you have to do is show up with your shorts and swimsuit. Boat slip is optional. You can be in your boat and heading out to enjoy spectacular fishing, diving, snorkeling, boating, or just cruising and watching the sunset in a flash.brbrLocated on Lower Matecumbe this condo is in the city limits of Islamorada....'Sport fishing Capital of the World'! This gated community is beautifully landscaped and has a beautiful pool, hot tub, tennis courts, pickle ball courts, and exercise room. brbrKeywords: Keysey Condo Optional Boat Slip

2

Bed

2

Bath

4

Sleeps

$337.18

/ Nightly

Condo

Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip

Islamorada, Florida, United States

This opulent condo is located within Ocean Harbour which is one of Islamorada’s most sought after gated communities featuring 12 acres of lushly landscaped grounds, oceanfront pool & spa, club house, gym, tiki huts with a grilling area, lighted tennis court, and a marina with a boat ramp. This luxurious corner unit offers expansive panoramic ocean views, impressive custom kitchen & bathrooms, oversized screened-in porch and the finest furnishings that other units can’t offer. With a 50’ boat slip available upon request, you can enjoy the convenience of easy and quick access to world class fishing, diving, and snorkeling right out of your backyard. Head just a few miles south and travel through Snake Creek to access the Florida Keys Bay and Everglades National Park. Fish the flats for snook, redfish, bonefish, tarpon and permit or head offshore for sailfish, mahi-mahi, snapper, wahoo and more.brbrNot a fisherman No problem! This home is located only 1 mile from Founders Park and features a bayfront beach, olympic size swimming pool, kids splash pad, picnic areas, playgrounds, fitness and walking trails, basketball court, soccer field, baseball field, pickle ball court, and a golf driving cage (Park entry fee required). A 5-10 minute drive north or south will take you to Key Largo or downtown Islamorada, both offering endless restaurants, breweries, shopping, and activities. Key West is a scenic 2 hour drive south. 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.

Bed

Bath

Sleeps

$354.76

/ Nightly

Private Vacation Home

Beautiful, Spacious, Single Story Home - Islamorada

Islamorada, Florida, United States

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

3

Bed

2

Bath

6

Sleeps

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