Vacation Rentals By Owner In Islamorada, FL

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 559 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Hotel

Relax and Recharge! Pets Allowed, Outdoor Swimming Pool, Free Parking!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1180.83

Welcome to Maison 402 Island Charm, your perfect vacation retreat in the heart of Islamorada! This charming 3-bedroom, 3.5-bathroom townhome offers a blend of comfort, luxury, and convenience, making it the ideal home away from home.brbrNestled in a prime location with breathtaking ocean views, Maison 402 Island Charm provides easy access to an array of restaurants and shopping destinations in downtown Islamorada. Whether you're a foodie eager to explore local cuisine or a shopper looking for unique finds, you'll be just steps away from the best that Islamorada has to offer.brbrAs you step inside, you'll be greeted by an open-concept living area that features coastal decor and ample seating. The fully equipped kitchen, complete with modern appliances and generous counter space, is perfect for preparing delicious meals for family and friends.brbrEach of the three cozy bedrooms is thoughtfully appointed with comfortable furnishings and soft linens to ensure a restful night's sleep. brbrOutside, the private patio area invites you to relax and soak in the stunning ocean views. Whether you're sipping your morning coffee or enjoying an evening cocktail, this serene outdoor space is perfect for unwinding and taking in the beauty of Islamorada's waters. brbrBook your stay at Maison 402 Island Charm today and experience the perfect vacation. With its prime location, luxurious amenities, and stunning ocean views, this townhome is the perfect choice for your next vacation.

Condo

Discover Maison 402 Island Charm in Islamorada: a spacious 3BR condo for 6 with stunning views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$184.27

** 60 day minimum in peak season (January- March)brbrEnjoy the timeless charm of Old Salt Retreat. brbrThis cozy and classic 2 bedroom, 2 bath canalfront home is thoughtfully appointed with all the essentials. Offering a warm and inviting living space, fully equipped kitchen, comfortable bedrooms and a spacious Florida Room overlooking the canal. brbrThe property offers 65 feet of deepwater dockage with easy access to world-class fishing and diving spots. Enjoy backcountry fishing right in your backyard or hop over to the oceanside via Channel 5 Bridge. brbrThe Port Antigua neighborhood is one of the best in Islamorada, offering private access to a stunning sandy beach with crystal-clear waters, perfect for swimming, sunbathing, and unforgettable sunsets. Plus, the neighborhood boat ramp provides convenient access for launching your boat with ease. brbrLocated in one of Lower Matecumbe's favorite neighborhoods, Old Salt Retreat is only minutes away from downtown Islamorada and Marathon.brbrBook now and experience the charm of a classic Islamorada vacation in a neighborhood that has it all.

Classic 2 bedroom, 2 Bath Islamorada Home with Dockage

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1321.88

Deep water dockage & heated pool! brbrModern, clean & fresh interiors make this rental perfect. brManatees visit the dock daily - they are sweet, gentle giants!brDock is about 75’ long on and located on a protected, deep water basin seconds from open water. 2 paddle boards & 2 kayaks for guest use.brbrThis Bayside house with a gorgeous heated pool and deep water is centrally located in the heart of the Village of Islamorada. The house is walking distance to the most of what makes Islamorada so special. It is only a 1/2 block from famous Lorelei Cabana Bar & Restaurant and 1/2 block from the Casa Morada Hotel. Large open living/dining/ kitchen area overlooking a partial view of open ocean on Bayside. Back Country Fishing is minutes away as the house sits only one property from open ocean. It has 3 master suites with king each, 1 king bedroom and 1 additional bedroom with twin beds. brbrModern, clean & fresh interiors make this rental perfect. brManatees visit the dock daily - they are sweet, gentle giants!brDock is about 75’ long on and located on a protected, deep water basin seconds from open water. 2 paddle boards & 2 kayaks for guest use. The waterfront pool is heated to 86 degrees.brbrPlenty of boat trailer parking onsite.brbrTHIS PROPERTY RENTS SATURDAY TO SATURDAY - we might make exceptions but during high season we have Saturday to Saturday bookings only.brbrIslamorarda has so much to offer, amazing restaurants, aqua blue waters, incredible fishing and boating! brThe restaurants within walking distance: Lorelei Restaurant, Islamorada Beer Company, Morada Bay Beach Café, Pierre's Chef Michael's, Kaiyo Grill, Keys Brewery, Bayside Gourmet, Bayside Gourmet, Bitton Bistro and Mangrove Mike’s.brbrbrAbout the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel ; it is exceptionally clean and easy to enjoy.brbrWe privately own a total of 5 boutique vacation rentals in Islamorada:brVRBO listing #1576833 (5 bedroom)brVRBO listing #1054019 (5 bedroom)brVRBO listing #1977457 (7 bedroom)brVRBO listing #689629 (5 bedroom)brbrLICENSE #: 26-0278 - Islamorada

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Islamorada, Florida, United States

Bed

Bath

10

Sleeps

$3887.82

Villa

PRIVATE BEACH / Heated Pool / volleyball court/ Orchid Beach Key

Islamorada, Florida, United States

Bed

Bath

12

Sleeps

$2382.59

Welcome to Infinity Bay Islamorada – an infinite paradise with endless possibilities in the heart of the Florida Keys. This exclusive estate embodies sophistication and serenity, where guests can unwind in style against a backdrop of Florida Bay and swaying palm trees. At Infinity Bay, luxury meets tranquility, offering a tropical sanctuary where the pool and bay blend seamlessly into one breathtaking horizon.brbrThis magnificent 9-bedroom, 10-bathroom property redefines the meaning of a retreat. With over 7,000 square feet of living space between the main residence and a detached guest ap, there is ample room to relax, entertain, and indulge in comfort. Step inside the main house and be welcomed by floor-to-ceiling windows that flood the space with natural light, framing panoramic views of the bay. The open design and breezy ambiance set the tone for an unforgettable stay.brbrAt the heart of the main house lies a chef’s kitchen designed to impress. Outfitted with premier appliances, it features a six-burner gas range, two dishwashers, dual wine fridges, a beverage fridge, under-counter ice maker, built-in water filtration system, and a dedicated coffee station. Whether you’re cooking yourself or enjoying the services of a private chef, this space ensures every meal is extraordinary. brbrThe main house offers five spacious king suites, each with a private bath, plus an additional twin bedroom with an adjacent bath. The detached guest apartment provides further privacy and comfort, featuring two king bedrooms, one twin bedroom, two bathrooms, a full kitchen, living area, laundry, and a screened-in porch overlooking the lush tropical entryway gardens.brbrThe backyard is a private sanctuary, surrounded by lush tropical landscaping that maximizes both privacy and panoramic bayfront views. Spend your days lounging by the infinity pool, enjoying al fresco meals, or relaxing in the shaded cabana complete with its own full bathroom. Enhancing this outdoor retreat is a fully equipped kitchen featuring a built-in grill, beverage fridge, sink, and poolside bar seating—perfect for sunset cocktails or freshly grilled seafood by the water.brbrEntertainment is effortless with two outdoor TVs for game days or starlit movie nights, all elevated by a Sonos sound system that carries music throughout the property. For boating and water lovers, a 100-foot deep-water dock accommodates yachts, center consoles, or bay boats, making it the ideal launch point for on-the-water adventures.brbrAnglers will find themselves in paradise, with opportunities ranging from backcountry snook, redfish, and bonefish to offshore mahi, wahoo, snapper, and sailfish. Beyond fishing, the iconic Islamorada Sandbar and Alligator Light House invites you to swim, sunbathe, or float in crystal-clear waters.brbrInfinity Bay is a gated residence ensuring both privacy and peace of mind. Perfectly positioned in the heart of downtown Islamorada, guests are within quick distance of shops, dining, and attractions, while still enjoying a private resort-like escape. For those seeking adventure beyond Islamorada, Key West is just a two hours south, making it an easy and scenic drive for a day trip.brbrAt Infinity Bay, every detail is curated to elevate your experience. From dinner reservations at the finest local restaurants to planning private excursions, our concierge team can take care of everything so you can focus on enjoying paradise.brInfinity Bay Islamorada redefines the art of island living. 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.

Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada

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

Condo

Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat

Islamorada, Florida, United States

Bed

Bath

Sleeps

$625.14

PROPERTY NAME: Little Bay Cottagebr82246 Overseas Highway, Islamorada, FloridabrbrLOCATION: Cottage located directly on the Florida BaybrbrMINIMUM STAY: Weekly or MonthlybrbrMILE MARKER: 82.2brbrDETAILS: br- Located on a one-acre lush tropical setting in a gated compound directly on Florida Baybr- One of 3 separate units for rent by the week or month, each sleeping up to 6 peoplebr- Protected dockage for up to a 34-foot boatbr- Sunning area with lounge chairs on the peninsulabr- Hammocks, pergola, and tiki for relaxingbr- Panoramic views of Florida Bay from the covered balconybr- Spacious interior with 2 bedrooms, 2 bathrooms, and a queen-size sleeper sofabr- Updated kitchen with new appliances and granite countertopsbrbrLittle Bay's Cottage is a ground-floor home with a unique floor plan. The main living area is in the center of the house, with a kitchen, dining area, sitting area, and full bathroom. To the right is a large bedroom with a king bed and full bathroom. The laundry area with a full-size washer and dryer is also located in this room. To the left of the living area is an enclosed sunroom that can be used as a second bedroom at night. The sofa in the sunroom converts to a queen-size sleeper, and there is also a twin-size Murphy bed. The cottage offers a little more privacy than the duplex units, but it does not have water views.brbrThe three units are available for rent by the week or month. Each unit sleeps up to 6 people, so you can rent one or all of them for a family reunion. Protected dockage in the little bay can accommodate boats up to 34 feet long. There is also a sunning area with lounge chairs on the peninsula, as well as hammocks, a pergola, and a tiki hut. All of the units have central air conditioning, a flat-screen TV in the living room, and WiFi. brbrSLEEPING ARRANGEMENTS: Sleeps 6 comfortablybrPrimary Bedroom: King Bed, Bathroom with Shower brGuest Bedroom: Queen Sleeper Sofa and Twin Murphy Bed, Bathroom with showerbrbrAMENITIES INCLUDE: Dockage for up to a 34 ft boat, Charcoal grill, Hammocks, Pergola, Swim and Snorkel in the bay. There is also Cable TV, WiFi, washer and dryer, air conditioning and free parking. brbrACTIVITIES: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures. Near by, there is John Pennekamp Coral Reef State Park, Theater of the Sea, Robbie's Marina and Islamorada Fishing Pier.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.

Cottage

Lush tropical plantings in a gated compound located directly on the Florida Bay

Islamorada, Florida, United States

Bed

Bath

Sleeps

$241.93

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Apartment

Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed

Islamorada, Florida, United States

Bed

Bath

Sleeps

$255.41

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 904 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool is available.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Hotel

Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed

Islamorada, Florida, United States

Bed

Bath

Sleeps

$241.93

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Apartment

Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking

Islamorada, Florida, United States

Bed

Bath

Sleeps

$241.93

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 380 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $50 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Apartment

Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast

Islamorada, Florida, United States

Bed

Bath

Sleeps

$759.45

brPrivate 2acre Single Family Home awaits! Just another day in Paradise. Located at 75.7MM!brbrCozy, quiet, 3 bedroom (1 King, 1 Queen, 2 Twins) 2 bath home offers spacious eat in kitchen, quartz & granite counter tops, dining area, fabulous tile flooring throughout, glass floor to ceiling, lots of natural light, bath and a half, and an outdoor shower!! Master bedroom has private bath, private entry and glass floor to ceiling views that take your breathe away. All bedrooms equipped with cable television and secure WIFI throughout. Excellent space for outdoor entertainingbrbrExtremely unique and rare property with private 600ft drive offering Private 100ft beach, Bay front deep water dock, walk into bay, shallow water for swimming, fishing off dock and so much more.brbrIt offers prestige un-thought of million dollar sunsets!! brWorld Class sport fishing, scuba diving, snorkeling, kayaking, paddle board all in your front yard!!brOwner Occasionally occupies 2 acre Property adjacent to property, rarely shared dock with owner onlybrPerfect location for a beach wedding, family reunion, or a peaceful getaway!! Bring your boat! What are you waiting for

Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock

Islamorada, Florida, United States

3

Bed

Bath

6

Sleeps

$191.72

Escape to this quaint 2-bedroom, 1-bathroom conch-style cottage in the heart of Islamorada. The fully equipped kitchen and cozy living space invite you to feel right at home, while the Keys-style Florida room offers a breezy spot to soak up the beautiful winter weather.brbrUnwind in the private hot tub or lounge in one of the many outdoor seating areas, ideal for sipping your morning coffee or enjoying evening cocktails under the stars. With a spacious, fenced-in yard featuring lush, green grass, this cozy retreat is perfect for those seeking relaxation and tranquility.brbrLocated in an unbeatable downtown spot, you’ll be just a short stroll from the vibrant Morada Way Art District, filled with galleries, shops, and local charm. Whether you're here for adventure or a peaceful getaway, this cottage is your perfect home base.brbr28 night minimum. Please inquire for rates and availability.brbrKeys Cottage ~ MM81 Oceanside

Quaint Islamorada Cottage with Unbeatable Location

Islamorada, Florida, United States

Bed

Bath

Sleeps

$667.11

Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.brbr2 Bedrooms, 2 baths. brbrCaribbean homes with 450-foot fishing pier and beach entry pool keep guest coming back. Its the off-shore fishing and diving that makes it so hard to leave. Located on a deep-water channel with protected dockage. 1 King Bed, 2 Full Beds, 1 Pull Out

Luxurious Caribbean 2 Bedroom 2 Bath Home

Islamorada, Florida, United States

Bed

Bath

Sleeps

$458.9

Angler's Reef #118 - Angler's Reef is a beautiful oceanfront gated community located in Islamorada. This modern updated two bedroom two and a half bath unit is nicely appointed with granite countertops, stainless appliances, wood floors, dining room seating for four and tasteful decor and furnishings. The unit offers ground floor living room, dining area, kitchen and half bath. The second floor opens up to a king master en-suite with covered balcony and two twin bed en-suite. The complex is comprised of 52 Key West style homes and 30 boat slips. Meticulously landscaped gardens surrounding a private heated oceanfront swimming pool, sunning beach and launch area for your paddle boards and kayaks. brAdditional $400 dockage fee per week. Ask for availability.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. Vacation Rental License # 24-0428brPlease 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.

Angler's Reef 118: Charming 2BR condo in Islamorada with pool and beach access

Islamorada, Florida, United States

Bed

Bath

Sleeps

$526.48

2 bedroom, 2 bath with 1 king bed, 1 queen bed and 1 queen sleeper sofa. Sleeps 6. Boat dockage and Housekeeping NOT available.brbrGuests enjoy the beautiful Caribbean décor and open ceilings. Solid wood doors and windows, ceramic flooring. Open living and dining area all add to your tropical experience. You are just across the street from The Caribbean Resort and are welcome to enjoy our beach-entry pool and fishing pier. brbrHome includes, washer-dryer, wireless Internet, and cable TV. Daily Housekeeping and Boat Dockage NOT not available.

New Ground Level Caribbean Cottage

Islamorada, Florida, United States

Bed

Bath

6

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

Condo

Ocean Harbor Paradise in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$858.42

Welcome to Lobster Tales, a stunning bayfront home in the heart of Islamorada's Plantation Key Colony. This spacious 5-bedroom, 5-bathroom retreat is designed for comfort, privacy, and endless enjoyment of the Florida Keys lifestyle. Downstairs, with its own private entrance, you'll find a complete 1-bedroom, 1-bath apartment with a full kitchen and living area — perfect for in-laws, extended family, or guests seeking their own space. brbrUpstairs, the main level offers an open kitchen and living room framed by wide bay views, along with two bedrooms and two bathrooms. Just off the living room, a large screened porch invites you to relax and take in the spectacular sunsets over Florida Bay. The upper level features another guest room with private bath and the master suite, a true sanctuary with a private gym overlooking the bay, a spacious master bath, and plenty of room to unwind.brbrOutside, the property is designed for making the most of island living. A large veranda overlooks the water, while a private dock with boat lift (available for $1,500 per month) provides quick access to the bay. Guests can take advantage of the included kayak and paddleboard, then return to soak in the hot tub or rinse off in the outdoor shower. From sunrise paddles to sunset gatherings, Lobster Tales offers the perfect blend of luxury, relaxation, and adventure in one unforgettable bayfront setting.

Lobster Tales: A stunning 5-bedroom, 5-bath home in Islamorada with bay views.

Islamorada, Florida, United States

Bed