Vacation Condo Rentals By Owner In Islamorada, FL

Get ready to experience an incredible Islamorada vacation at Maison 305, located in the heart of Islamorada, FL. This waterfront gem is your ticket to luxury, comfort, and tranquility all rolled into one unforgettable getaway.brbrThe moment you walk through the doors of Maison 305, you'll be greeted by a perfect blend of modern style and coastal charm. The spacious living area is decked out with elegant furnishings, calming colors, and breathtaking views of the turquoise waters that define the Florida Keys. Kick back on the plush sofas, soak in the natural light pouring through the windows, and let all your worries fade away.brbrMaison 305 couldn't be in a better spot, surrounded by Islamorada's top-notch attractions, from fantastic dining and shopping to outdoor adventures. Dive into the vibrant coral reefs at Alligator Reef, take a boat ride, or simply take a leisurely stroll through the heart of Islamorada and explore all the best local shops! brWhether you're after a romantic escape, a family retreat, or a fun-filled getaway with friends, Maison 305 promises the ultimate blend of luxury, coziness, and peace. Immerse yourself in the enchantment of Islamorada at this sanctuary. Secure your stay now and create memories that will stay with you forever.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.

Charming 3-Bedroom Condo in Islamorada with Stunning Ocean Views and resort-style pool.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$206.57

Wake up and enjoy sunrise on the pier over the Atlantic and walk across the street at night and watch sunset on the Gulf. You can take a dip in the pool or play a game of pool in the club house. Visit one of the many local restaurants (some close enough to walk to) or prepare dinner yourself in the beautiful kitchen or grill a steak outside by the ocean. Fish off the pier or book a fishing trip!

Condo on Islamorada on the beautiful Atlantic Ocean.nCome enjoy and relax!

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$292.87

Welcome to Coral Harbour Club! brbrFind your escape, experience relaxing days at this oceanside getaway! Located on Plantation Key in Islamorada, this 2 bedroom, 2 bath condo is equipped to sleep six adults, with the bedding arrangements of one king bed and two queen beds. The oceanfront marina and swimming pool, private clubhouse, saltwater lagoon, and tennis courts are ready to make your stay at Coral Harbour a memorable one.brbrEnjoy your month-long vacation in your own little tropical oasis. Savor your morning coffee out on the terrace or bring down the screen and take advantage of the cool ocean breeze. Don’t feel like cooking You’re in luck, this condo is only a short drive away from some of Islamorada’s best dining – casual and upscale.brbrFinding dockage is not a problem as this unit comes with a boat slip. The protected onsite, oceanside marina can accommodate up to a 30’ boat. This marina also has its own boat ramp, fueling station and ice machine. Only minutes away from the famous “Alligator Lighthouse,” snorkeling, diving and all kinds of fishing! Additionally, there is easy bay access with Tavernier Creek and Snake Creek nearby. There is no trailer parking onsite, but you can try the Plantation Yacht Harbor at Founders Park for trailer parking options.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.brbrPlease book 45 days advance so HOA can approve guests and reservation.

Coral Harbour Club ~ 2 Bedroom Condo in Islamorada with Pool & Dockage

Islamorada, Florida, United States

Bed

Bath

Sleeps

$510.29

Welcome to Mother Ocean! brbrThis stunning ocean view condo boasts three bedrooms and two full bathrooms, making it perfect for a family or group of friends. It features modern amenities and coastal decor throughout, providing a comfortable and inviting atmosphere for your stay. The spacious living room offers captivating views of the ocean, and opens up to a large screened-in balcony where you can enjoy watching the morning sunrise or spot manatees in the afternoon. The fully equipped kitchen comes with a few extra features such as a coffee bar, air fryer oven and bar seating. The master bedroom has a king-sized bed and its own private bathroom that boasts a walk-in shower, jetted tub, double vanity sinks and a water closet. The second and third bedrooms offer queen and full-sized beds and share a full bathroom. Other amenities include a washer and dryer, central air conditioning, cable TV, and high-speed internet throughout. brbrThe condo is located in the sought after Bay Harbour community on Lower Matecumbe Key. This resort style community offers a pool, hot tub, fitness center and tennis and pickleball courts. If you're an angler, you'll appreciate the 30’ deep water dock with water, electricity, fish cleaning stations, and a locked storage closet for your gear. You can rent a boat, kayaks, or paddleboards, and they can be delivered directly to your own dock. With direct access to the Florida Bay, you can head straight out to the Everglades National Park and fish the flats for snook, redfish, bonefish and permit. Or, take a quick ride to the oceanside for sailfish, mahi-mahi, snapper, wahoo and more! With close proximity to the famous Islamorada sandbar, you can experience the unforgettable crystal clear waters and relaxed atmosphere. During spring and summer, fish Channel 2 or Channel 5 bridge for the world famous “Silver Kings” (tarpon) for a fierce fight. Dockage must be reserved prior to arrival and is included in the rate. There is no trailer parking on-site, but you can try Seabird Marina for trailer parking options.brbrAt the top of the neighborhood is a local seafood market with fresh local lobster, fish, shrimp and more. 1.5 miles south you will find Anne’s Beach; A hidden gem featuring a winding boardwalk that meanders through the mangroves and sheltered picnic areas where you can have lunch while watching the ocean! Anne’s Beach is also a popular place with windsurfers, and if it’s a breezy day, it’s fun to watch them swoop and soar. Because of the expansive area of shallows in the area, the best activity is to wade and enjoy the year round warm turquoise waters.brbrIslamorada is located in the heart of the Florida Keys, offering a prime location for your vacation. Whether you prefer deep-sea fishing, exploring the backcountry shallows, diving or snorkeling the vibrant reefs, sailing, kayaking, parasailing, or windsurfing, there's something for everyone to enjoy. 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 stores. Key West is a beautiful 1.5 hour drive south.brbrTake advantage of a local’s secret and park your vehicle and utilize the Islamorada Freebee; Our local rideshare service offering door-to-door transportation service to and from your favorite Islamorada destinations with environmentally friendly electric vehicles. It’s not only a fun alternative transportation option – it reduces traffic congestion, addresses drinking and driving, and reduces the Village’s carbon footprint. Two Tesla Model X vehicles can accommodate up to seven passengers and one larger vehicle that can accommodate a wheelchair and up to nine passengers. 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.brbrIslamorada Vacation Rental License #: 26-0098

3 Bedroom Islamorada Condo w/ 30' Boat Slip & Ocean Views!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$215.09

Escape to Islamorada and enjoy the laid-back lifestyle of the Florida Keys in this 2-bedroom, 2-bathroom condo at Plantation by the Sea. This charming getaway offers a comfortable stay in a gated community with fantastic amenities—perfect for your next vacation!brbrStep inside to find an inviting living space with coastal-inspired décor, a fully equipped kitchen, and all the comforts of home. The primary bedroom features a king-size bed and a private ensuite bath, while the second bedroom provides a cozy retreat for family or guests, with easy access to the second full bathroom.brbrYou're just a short walk to the heated pool, fitness room, and sauna. Take a relaxing dip, unwind after a workout, or stroll down to the private fishing pier, where you can soak in the ocean breeze and watch stunning sunrises over the Atlantic.brbrLocated in Islamorada, you're minutes from world-class fishing, delicious waterfront dining, and unique local shops. Whether you're planning a quick escape or an extended stay, this condo offers the perfect mix of comfort and convenience.brbrBook your stay today and experience the best of the Florida Keys! 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.

Cozy 2-Bedroom Condo in Islamorada Plantation By The Sea

Islamorada, Florida, United States

Bed

Bath

Sleeps

$156.29

1 bedroom apartment new to the rental market! Modern and updated, this first floor unit has a gorgeous kitchen with stainless steel appliances, large pull out couch and a garden view and a private balcony. Comfortable & cheerful, a place to relax between fishing trips. Stairs required. brThe SpacebrThe condominium is right on the bay with two pools (one heated), a beach area, workout room, game room, community room, fabulous sunsets and friendly residential atmosphere. Safe and secure gated community with elevator access.brbrFeatures/Location DescriptionbrSummer Sea is a multi-story residential waterfront condominium with a friendly atmosphere with on-site management. The perfect place to spend your vacation. This condominium is on Plantation Key just north of the famous Marker 88 Restaurant, a 5-star gourmet restaurant with outside bar. Four restaurants within walking distance. The complex is located at mile marker 88.5 which is within The Village of Islamorada. With an abundance of community areas such as a beautiful sandy area and lots of space to stretch, large, shared kitchen/entertaining area, game rooms, a gym, beach, 2 pools (one heated), laundry rooms etc. br28-day minimum, Minimum rental of 2 months when renting February. No Pets, No Smoking.brFlorida Lease required. application and background check performed by the condominium is required. Summer Sea Condominium requires a 5-day notice, and their $200 fee is nonrefundable. If you cancel your reservation a 3% cancellation feel will be charged to cover costs. Please note that the security deposit will be held against your credit card three days before your arrival and released after departure. This is not a charge, just a hold until it can be verified that there is no damage. Feel free to inquire for all details.brOffered through Blue 9 Realty Inc., DBA Keys Vacation Brokers, Jonelle Kop, Tavernier, FL

NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125

Islamorada, Florida, United States

Bed

Bath

Sleeps

$202.84

This is a quaint, ocean side condo with full amenities and easy access for fishing, diving, snorkeling and much more.The apartment sleeps 2-4. It has a king bed in the bedroom, a pull out sofa bed in the living room, a fully equipped kitchen, a garage with additional fridge/freezer. Boat/trailer storage in boat yard included on availability and easy ramp access. Fish cleaning table and BBQ grill also on property.brbrThere is an ocean of things to do for everyone. Shopping, Keys themed restaurants both inexpensive and high-end all over the islands. There is swimming, tennis, pickle ball, snorkeling, diving, bird watching, historical interest, botanical, culture, kayaking, wildlife and pondering life. The property is a nature lovers dream with an occasional manatee in the canal, iguanas that sun themselves on the dock, pelicans, egrets and osprey that fly in for a hello there.brbrWe can accommodate a registered 25 ft boat, dockage is included in the rental on availability. There is a heated pool, tennis court, shuffle board and more.brbrThe area is world renowned for bonefish, permit, tarpon fishing and offshore fishing for dolphin, tuna, wahoo, swordfish, sailfish, etc. etc. etc. This can be your own personal paradise.

Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required)

Islamorada, Florida, United States

Bed

Bath

Sleeps

$239.16

Discounted 3 to 6 months rentals. Plan your perfect getaways to paradise. 1/1 Fully Renovated Beautifully Designed Condo. Mm76 Sleeps 4. Boat dock equipped with water, electric & cleaning station as well as boat & trailer storage first come/ serve. 300k liability insurance required for boat. Private boat ramp also available. Enjoy all the community amenities pool, tennis court, pickle ball, shuffle board, corn hole, & life size tic tac toe. Building shares a washer & dryer. Bring home your Fresh Catch & prepare it in our fully equipped kitchen with all new appliances and a fully stocked for all your prep & cooking needs. We also provide a Weber gas grill. Condo is located on the 3rd floor. Minutes from the Famous Robbie’s and Anne’s Beach. Enjoy an array of restaurants , breweries, bars, shopping, fishing charters, dive & snorkel shops as well as weekly farmers markets. Islamorada full moon parties are always a great idea. Paradise Found

Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat

Islamorada, Florida, United States

1

Bed

1

Bath

5

Sleeps

$351.08

Talk about an Atlantic Ocean View; you've found it! You will fall in love as soon as you enter the gates at Ocean Harbor. This 2 bedroom, 2 bath unit offers everything you need for Resort Style Living. Enjoy the amenities of the pool, hot tub, tiki hut, tennis/ pickle ball, dockage, clubhouse, and gorgeous landscaped grounds. The private spiral staircase off of the Florida room will take you down one flight directly to the sparkling pool. The included boat slip can accommodate a boat up to 30'. You will be boating, fishing, snorkeling, or a sunset cruise within minutes from the dock. This unit offers an assigned covered parking spot as well. Conveniently located in Plantation Key. Close to shopping, boutiques, breweries, marinas, dive shops, hospitals, and many well-known restaurants. A short commute from Miami and a beautiful drive to Key West. Contact us today to get your vacation started. brCondo association approval is required, along with a $100 fee.brBoat Insurance is required for the slip. There is no trailer storage. One Pet (dog ) will be considered.br

Ocean Harbor Paradise in Islamorada

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$141.34

This studio makes the best of the space. Living room by day bedroom by night with the convenient Murphy bed. All newly updated. Enjoy The heated & cooled pool, Lounge by the beach overlooking the Florida Bay. It has a perfect view of nightly beautiful sunsets. This condo has saunas, a lovely beach with a fire pit, BBQ grills, fish cleaning stations, billiards room. Whether you want to relax around the pool and enjoy the property or go kayaking and paddle boarding, fishing, there is plenty for everyone.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. 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.

Charming Summer Sea 203 in Islamorada: 1 bed, heated pool, and ocean views!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$231.38

Watch the sunrise from your private balconies in both bedrooms overlooking the Atlantic ocean, and walk across the street to amazing sunsets on the Gulf of Mexico in Founder's Park or Marker 88 Restaurant. brbrEnjoy the fully renovated condo with wood floors, marble in both bathrooms, granite countertops, a 55 TV in the living room, high-speed WiFi, and reclaimed wood bar. The kitchen has all the equipment and utensils you need to make a great meal, and a community BBQ is located just below the unit by the water. Clean up is easy with a in-unit dishwasher, washer and dryer.brbrWe are located an hour south of Miami and you will be less than two hours north of Key West - a perfect day trip. Islamorada is the fishing capital of the world, with charter captains available to take you on the water on your whim.brbrThe property has a small exercise room (run or walk on the treadmill while looking at the ocean waves!), a lovely heated pool with lots of loungers and rockers, a beautiful dock and a community BBQ to grill your catch on.brbrWe have a small, friendly, community of 80 units, and are looking forward to hosting great people. Please reach out today so we can discuss your Keys dreams.

Oceanfront condo in Islamorada, amazing sunrise views, renovated in 2019!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$899.83

Maison Matecumbe #307 - 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, brand new kitchen, beautiful bathrooms, decor and bedding. The unit offers an open lower level living room with kitchen and guest bedroom and full bath. Beautiful views of the Atlantic from the screened balcony. The upper level has a king master en suite and third bedroom with two queen beds. Newly renovated swimming pool and hot tub to spend your days lounging along with Maison's beach, outdoor kitchen, tiki hut and spa. brVACATION RENTAL LICENSE: 24-0074brIf 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.

Experience luxury at Maison 307 in Islamorada, 3 bedrooms with resort-style pool.

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$161.21

Bayfront Sand Pebbles #304 - A desirable Islamorada condo complex with a total of only 16 units. This two-bedroom two bath unit is tucked away on the bay right in the heart of Islamorada. Beautiful sunsets & water views from your living room, kitchen & master bedroom. Enjoy the spacious lanai and refreshing breezes! Relax at the pool or venture through the mangrove nature walk. Islamorada Marina, Square Grouper and Midway Cafe are all in walking distance. brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Relax in this 2-bedroom bayfront condo in the heart of Islamorada!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$305.31

Escape to a tropical paradise at this villa at Topsider Resort in Islamorada. Nestled among lush gardens, this private octagon-shaped stilt house offers a large balcony, a fully equipped kitchen, cozy living spaces, and complimentary amenities like WiFi and cable TV. Guests can enjoy a heated pool, private beach, Jacuzzi, and the famous 180' T-shaped pier stretching into the bay. The villa blends comfort with the vibrant island atmosphere of the Florida Keys.brbr• Oceanfront Private Beachbr• Heated Outdoor Poolbr• 180' T-shaped Pierbr• Spacious Private Balconybr• Fully Equipped Kitchenbr• In-Suite Washer and Dryerbr• Complimentary Boat Docking (up to 23')brbrWelcome to this charming 2 Bedroom Condo, perfect for families or couples seeking an unforgettable retreat in the Florida Keys.brbr• Master Bedroom: Queen-size bed, en-suite bathroom, closetbr• Second Bedroom: Two twin beds, closetbr• Bathrooms: Bathtub/shower combos, towels, essentialsbr• Living Area: Queen sleeper sofa, cable TV, access to balconybr• Kitchen: Full-size fridge/freezer, stove, oven, microwave, dishwasher, coffeemakerbr• Dining Area: Seating for 4br• Private Balcony: Views of lush tropical surroundingsbrbrOther amenities available at Topsider Resort include (but are not limited to):brbr• Jacuzzibr• Shuffleboard Courtsbr• Tennis Courtsbr• Bicycles and Kayaksbr• Charcoal Grills and Picnic AreasbrbrLOCAL FAVORITESbrbrFood & Drinkbrbr• Lazy Days South: Fresh seafood and tropical drinks with ocean views – 1.2 mibr• Hog Heaven: A laid-back BBQ joint famous for its smoked meats and casual island vibe – 2.5 mibr• The Fish House: Popular seafood restaurant offering local specialties and a relaxed atmosphere – 6.1 mibrbrOutdoor Activitiesbrbr• Alligator Reef Lighthouse: Snorkel among colorful coral reefs and tropical fish – 7.8 mibr• Florida Keys Overseas Heritage Trail: Scenic biking and hiking trail – 2.2 mibr• Robbie's of Islamorada: Feed tarpon, rent paddleboards, and enjoy waterfront dining – 5.4 mibrbrRecreational Activitiesbrbr• Theater of the Sea: Interactive marine park featuring dolphins and sea lions – 3.0 mibr• History of Diving Museum: Fascinating exhibits on diving history – 4.1 mibr• Islamorada Seafood Festival: Annual event celebrating fresh local seafood and live music – 6.0 mibrbrOTHER THINGS TO NOTE:br• Parking: Parking available for 2 vehicles per reservation at the resort.br• Pet Policy: Sorry, this is not a pet-friendly property.br• Smoking: No smoking permitted; fines up to $1000 apply for violations.br• Other Notes: Condo assignments are made at check-in; views and layouts may vary. Hair dryers available upon request. Quiet hours are from 10 PM to 7 AM (Sun–Thu) and 11 PM to 7 AM (Fri–Sat).br• Room assignments may differ from the photos, as each unit is unique.br

Beachfront Villa w/ Pier & Pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$341.25

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.

Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$122.65

Whether you spend your next Florida vacation playing in the cool surf or hanging out with good friends on the private patio, you will love staying in this gorgeous retreat. Guests will be delighted by the fantastic location of this condo, offering a large pool, 2 tennis courts, a furnished clubhouse, first-come-first-serve dockage, and a bayfront beach ideal for kayaking and paddleboarding. Whether you're looking to relax by the pool or explore the water, this condo has everything you need for a memorable vacation. brbrInside, an open and spacious living area features comfortable furniture, attractive wall art, and a large TV. The full kitchen is loaded with stainless steel appliances and enough counter space and cookware to inspire any family chef. Serve your dinner guests at the handsome wood dining table while the kids swing their feet from the barstools of the breakfast bar. You can take your breakfasts outside as alfresco meals to enjoy the gardens and walkways while you eat under the table umbrella. Use the free WiFi to research your next adventure or download an excellent playlist to your device for a trip to the shared tennis court. You'll love streaming your favorite Netflix movies with the kids and lots of hot buttered popcorn. The shared pool is a great way to cool off after a hot-weather hike on one of the many nearby trails. One of the guest bedrooms has access to a private balcony.brbrYou'll have many great restaurants nearby whenever you need a break from the kitchen. Book a trip through Capt. Easy Charters, one and a half miles southwest, to reel in today's limit of saltwater fish! Ready to crash some waves You can rent equipment and find all kinds of swimwear and accessories when you visit Otherside Boardsports, less than five miles south.brbrTHINGS TO KNOW brThis home does not have any ground-floor bedrooms.brThis property is managed by Vacasa Florida LLC.

Beautiful, sunlit home with pool, tennis court & beach access - near the marina

Islamorada, Florida, United States

Bed

Bath

Sleeps

$226.76

PROPERTY NAME: Beacon Reef #307br83201 Old Highway, Islamorada, FloridabrbrLOCATION: Ocean side CondobrbrMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedbrMILE MARKER: 83.2brbrDETAILS: This like-new 2 bedroom/2 bath condo has fabulous ocean views and was totally remodeled/updated very recently. You'll love the sparkling new natural stone counter-top kitchen with stainless steel appliances, induction cook top and microwave. The interior is bright, fresh and airy. The furnishings are comfortable and inviting. Dine at the glass top table or pull up a stool to the kitchen counter while grabbing a snack. Store up to 32 bottles of your favorite wines in the dual-zone wine cooler. Relax on the private balcony, gazing at the ocean or sunrise. Both bathrooms have been completely remodeled and all linens needed are provided. The oversized master suite offers a king bed, wide ocean views, separate entrance to the balcony and a huge bath with walk-in shower. The guest bedroom provides spacious accommodations for friends and family. You'll love the ease and convenience of your own new washer/dryer and secured Wi-Fi. Two large flat screen TV's means you'll want for nothing in this captivating condo. Maximum number of guests is 4. brbrBeacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your own private balcony overlooking acres of lush tropical landscaping and gazing at the magnificent ocean views. Gather your ration of Vitamin D by simply lounging next to the free form swimming pool. Dock your boat in the marina. Dockage is first-come. Jet Skis and PWC are not permitted. Fillet your fish at the fish cleaning station. Exercise in the fitness center. Indulge your aching muscles by soaking them in the spa hot tub after a hard day of fishing, diving or snorkeling - or anytime that suits your fancy! This property is professionally managed by Keys Holiday Rentals. brbrSLEEPING ARRANGEMENTS: Sleeps 4 MaxbrPrimary Bedroom: King Bed Bathroom with ShowerbrGuest Bedroom: King Bed Bathroom with ShowerbrbrAMENITIES INCLUDE: Condo has community pool/hot tub, Indoor community space, outdoor BBQ, and gymbrbrACTIVITIES: 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. brbrRESERVATIONS ARE NOT CONFIRMED UNTIL THE REQUIRED CONDOMINIUM ASSOCIATION APPLICATION IS APPROVED.

This condo is located in one of Islamorada's most prestigious condo complexes.

Islamorada, Florida, United States

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Bath

Sleeps

$210.0

Come, Enjoy and Relax in our beautiful piece of the paradise in the Florida Keys. The Executive Bay Club is located in Islamorada, the Diving/Snorkeling and Sport Fishing Capital of the world! This is a private, gated community with 24 hour security and easy accessible parking. The grounds have 2 tennis courts, heated swimming pool, club house, private beach and fishing dock. brbrOur two story unit has been renovated. The master bedroom has a king size bed, a renovated bathroom is adjacent. The second bedroom has 2 queen size beds and its own newly renovated bathroom television and DVD player. Downstairs relax in our living room, that sports a big screen TV or enjoy the quite patio right outside. There is also a dining area, kitchen with full size dishwasher, microwave, refrigerator and washer and dryer and an additional renovated bathroom with shower. The unit is fully furnished and we provide cooking utensils, dishes, linens and towels. However, bring you own pool/beach towels.brbrNext door is Founders Park, known to be one of the Keys most beautiful parks, with baseball, soccer fields, exercise equipment, basketball courts, tennis courts and pros available for tennis drills, lessons and round robins, private beach and playground, boat marina and public boat ramp. Let's not to forget the heated Olympic size pool with diving and lap areas, where swim lessons are available. Minutes away are your charter boats and captains, your scuba and snorkeling trips and wind sailing lessons. Our water is clear and our reefs are impressive! Don't forget to stop by the local art galleries, 'Theater of the Sea', a Marine Adventure where you can swim with the dolphins or drop by the Diving Museum. The activities are plentiful... water sports, kayaking, jet skis, parasailing, boating, sunset cruises and just reading and relaxing on the beach! The restaurants are the best in the Keys with local fish served daily. brbrSorry No Pets or Nor SmokingbrbrSo come, relax and Enjoy whatever your pleasure may be!brbr

Islamorada Spectacular Vacation At Executive Bay Club

Islamorada, Florida, United States

Bed

Bath

Sleeps

$431.44

The Artist's Cottage at Anglers Reef #136 - This beautiful home is located in Angler's Reef, a gated oceanfront community located in Islamorada. The owner has shared his own personal artwork throughout the unit for guests to enjoy. Angler's Reef is known for its beautiful tropical landscaping and colorful houses. It features a heated oceanfront swimming pool and beach. This two bedroom, two-and-a-half-bathroom unit has a very welcoming feel. Enjoy quiet mornings on the porch and days spent at the beach and pool.brVACATION RENTAL LICENSE: 24-0392brIf 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. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Discover Angler's Reef 136: a stylish 2-bedroom condo in the heart of Islamorada.

Islamorada, Florida, United States

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Bath