Vacation Home Rentals By Owner In Islamorada, FL

$741.59

Luxurious 4BR retreat at 115 Vilabella Drive, Islamorada, with a private pool.

Islamorada, Florida, United States

Located in Islamorada's premier neighborhood of Venetian Shores, this stunning 4-bedroom, 4-bath waterfront home offers the perfect balance of comfort and coastal style. Inside, you'll find an open-concept layout with a modern kitchen, spacious island, and high-end appliances—ideal for entertaining or family gatherings. The living area opens to beautiful water views, creating a bright and inviting space to relax after a day on the water.brbrThe lower level offers additional flexible living space, including a bonus room that leads directly to the pool deck. There is also an additional room that can easily function as a home office or extra sleeping space, complete with a sofa bed and its own bathroom—perfect for guests or convenient access from the pool area. A laundry room is also located on the lower level for added functionality.brbrOutside, enjoy a heated pool, outdoor kitchen, two outdoor TVs, dining area, and outdoor shower, all surrounded by lush tropical landscaping. For boaters, the property features concrete dockage on a deep-water canal with quick access to both the Atlantic Ocean and Florida Bay through Snake Creek.brbrThis home offers the ultimate Keys lifestyle with modern coastal design, exceptional outdoor living, and unbeatable access to Islamorada's world-class fishing, dining, and local attractions.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.

4

Bed

4

Bath

8

Sleeps

$440.48

/ Nightly

Private Vacation Home

Marlin Beach 3-bedroom house in Islamorada with private beach, hot tub and dock

Islamorada, Florida, United States

Nestled in Islamorada Sport Fishing Capital this fabulous house offers a tranquil retreat for guests seeking comfort and relaxation. With dock for your boat and three bedrooms featuring a king, queen, and twin bed as well as a double sofa bed in the living room there’s plenty of space for everyone. Two bathrooms include both a shower and a bathtub, perfect for unwinding after a day of adventure. Guests enjoy a cool, refreshing atmosphere thanks to air conditioning and heating throughout the home. Whether you’re gathering in the spacious living area or resting in the peaceful bedrooms, this awesome house provides a welcoming escape. Fall in love with Islamorada and enjoy the magic it has to offer.

3

Bed

2

Bath

6

Sleeps

$673.46

/ Nightly

Private Vacation Home

Impressive Resort Like 5 Bedroom / 4.5 Baths with Pool & Dockage in Islamorada!

Islamorada, Florida, United States

Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-bath home serves as an excellent setting for your tropical getaway. Ideally located in Islamorada on Lower Matecumbe Key, you will have convenient access to breathtaking views, casual and fine dining restaurants, shopping, water sport rentals, and just a short drive to the Bud N’ Mary Marina where you can charter a boat and head out for a deep sea adventure! Port Antigua community offers wide canals, boat ramp, and infamous bay front white sandy beach with tiki huts and picnic tables. These are private amenities and are only accessible by Port Antigua homeowners and guests. brbrAs you enter through the front door you are welcomed into the grand foyer that leads directly out to the pool and dock. Up the staircase you will find an open concept area complete with a spacious kitchen and a designated living room that includes comfortable lounge seating, perfect for a relaxing evening at home! The sliding glass doors off the living room open to reveal a balcony with picturesque views. Imagine sipping your morning coffee or afternoon cocktail while enjoying fresh sea air and an island breeze.brbrThoughtfully designed with you in mind, the intimate dining area sits adjacent to the kitchen with enough seating for six. The roomy kitchen grants space for any budding chef and comes fully-equipped with all the essentials to prepare gourmet, island- inspired meals at home! The large refrigerator, ample countertops and cabinet space ensures sufficient storage for all your necessities. Island-style furnishings and tropical decor sprinkled throughout the home elicit the peaceful vibes of Keys lifestyle.brbrWith five plentiful bedrooms to choose from, everyone in your group will enjoy some privacy in their pleasant accommodations. Each bedroom features comfortable bedding, TV’s with steaming service capabilities, ceiling fans and natural light. You will love waking up to the gentle Keys breeze and soft sunshine! The master suite offers a king size bed, private covered balcony, ensuite bathroom and an oversized closet. The main guest bedroom has a queen bed with an ensuite bathroom. While a second guest bedroom has a queen bed and convenient access to the hall bathroom. The third guest bedroom is located just up the stairs adjacent to the family room. And finally, the pool cabana that can also be utilized as a fifth bedroom as it features a sleeper sofa and full bathroom.brbrThe third floor offers a vast entertainment room, perfect for watching movies with an expansive U-shaped sofa, a bar area complete with mini fridge and cabinets full of games to play. Be sure to go out on the open lanai for peek-a-boo views of the Atlantic.brbrOutside you’ll find an impressive outdoor kitchen and eating area with ample space to entertain. Take a dip in the refreshing swimming pool or soak up some vitamin D in the comfy loungers. The 220 foot concrete dock features a gazebo, a fish cleaning station and two boat lifts. Enjoy your days resting by the water or take advantage of having canal access. This home is sure to check all the boxes for a relaxing and enjoyable vacation.brbrAdditional amenities include a washer and dryer, internet and parking. Learn more by calling 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.

5

Bed

4

Bath

10

Sleeps

$624.0

/ Nightly

Private Vacation Home

Luxurious 4BR home with open water views in Islamorada, perfect for families.

Islamorada, Florida, United States

Hidden gem in Venetian Shores with incredible bay views and stunning sunsets. This spacious and private property sits on a large fenced-in lot and offers the perfect setting for a relaxing Islamorada getaway.brbrThe outdoor space is truly special, featuring a heated pool, plenty of lounge seating, and beautiful open views of Florida Bay. Upstairs, the covered porch with a dining table overlooks the water, making it the perfect spot for morning coffee, outdoor meals, or watching the sunset over the bay.brbrThe main home upstairs offers 3 bedrooms and 2.5 bathrooms, along with bright living spaces that take full advantage of the beautiful water views. Downstairs there is a separate 1-bedroom, 1-bath apartment with a kitchenette, ideal for guests who want extra space or privacy. The downstairs apartment can be added to the rental for an additional $2,500.brbrThe property also features a rare walk-in sandy beach area along the bay, along with an observation dock perfect for sitting by the water, launching a kayak, or simply enjoying the peaceful surroundings.brbrWith its private setting, expansive outdoor space, heated pool, and incredible bay views, this Venetian Shores home is a truly special place to experience the Florida Keys.br1 small Pet will be considered at this home. (Please inquire.)brAlso note, this beautiful home is available for monthly rentals only.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

$493.29

/ Nightly

Private Vacation Home

Canal front home in Venetian Shores. Perfect for families . A boater's paradise!

Islamorada, Florida, United States

This canal front home is located in the prestigious Venetian Shores neighborhood. The perfect location right off of Snake Creek, which gives you fast access to both Ocean & Bay, fuel, bait, and provisions.brbrThis beautiful, updated canal home has two bedrooms, two baths upstairs and a one-bath studio apartment downstairs. It offers various sleeping arrangements. 8 people can be accommodated upstairs and 8 people downstairs. brbrThe House: brUpstairs has Two Bedrooms, a king-size bed in the Master with en-suite bathroom, a twin/full/twin bunk bed in the other guest suite. There is also a nice size guest bathroom upstairs. The couch upstairs has a large pull out couch and there is a day bed in the sunroom area with 2 twin beds. brbrDownstairs is a bunk room as it has four queen size bunk beds! Sleeps 8 people! Enjoy the convenience of a first-floor bathroom and a full, updated kitchen. Perfect for entertaining!brbrThe home is fully stocked with all kitchen supplies and upscale appliances (Cuisinart toaster oven/airfryer, convection oven, espresso machine, coffee maker, Ninja blender, all new knives and pots/pans). New washer/dryer in laundry room, games for family fun including: ping-pong table, corn hole set, darts, 3 cruiser bikes, and 2 kayaks). Pool is maintained each week has a cooler and heater and is lit at night. Outdoor table converts to a fire pit. Traeger grill is also provided. brbrThe Dock: Your 35-foot private dock with a boat lift provides instant access to fun – whether boating, fishing, swimming, or relaxing. Have your boats or yacht waiting just outside your door. Large, deep-draft sailboats or yachts are easily accommodated with a waterway 20 ft deep and 100 feet wide. Even tall vessels travel quickly between the Ocean and Florida Bay using the drawbridge just 1000 yards from the dock. With gas, bait, and tackle shops located before the bridge, your convenience is assured.brbrFounders Park is 3000 feet from the house: an easy walk or drive, or use one of the three beach cruisers we provide. You can enter free with your rental contract and enjoy the beach, walking paths, and family playgrounds. They provide small-fee access to swimming in the Olympic size pool - complete with diving boards, lap-lanes, and a separate splashpad for kids. Founders park is convenient for launching/loading boats at the boat ramp for nominal fees ($3/person pool, $20/ launch or loading boats). Larger boats are recommended to put in at the Harry Harris boat Ramp at mile marker 92.5 - just 6.5 miles from your rental & dock for the stay.brbrNon-shedding dogs (2 max) allowed with prior approval and $300 non-refundable fee. br28 day minimum - contact owner for more info and rates for long-term stays.br

Bed

Bath

Sleeps

$167.56

/ Nightly

Private Vacation Home

Pool, Beach and Tennis Court! Fishing, swimming and relaxation!

Islamorada, Florida, United States

Take it easy at this unique and tranquil getaway. Enjoy this well equipped 2 bedroom, 2 bath home. Enjoy beautiful sunsets . Fish, swim or snorkel while enjoying the bay view. close to some of the best restaurants and attractions in Islamorada. Walk to Founders Park to enjoy a beautiful beach, walking trails, picnic areas and playgrounds. Located in a private gated community with 24 hour security. No pets allowed. I am happy to offer early check in and late check out (if available/usually available) please ask if you need this accommodation. Available for a 28 day stay or more.

Bed

Bath

Sleeps

$423.99

/ Nightly

Private Vacation Home

PRIME LOCATION Islamorada Anglers Reef Oceanview Private Beaches, Pool & Marina

Islamorada, Florida, United States

Welcome to REELaxation! Everything you need for your Islamorada vacation is here. Picture this, gazing at the Atlantic Ocean from the heated resort style pool, watching the sunrise from one of the 2 private beaches, kayaking or paddle boarding to the famous Islamorada sandbar, catching dinner off the dock, soaking it all in on the porch seating with ocean views, reading a book on one of the 2 balconies and then having dinner nearby with some of the most amazing sunset views you will find. Imagine bringing all that to life in your own memory filled Islamorada vacation.brbrIn the middle row of Angler’s Reef, this 2-bedroom home accommodates up to 6 with the sleeper sofa. REELaxation offers kitchen supplies, Weber 3-burner gas grill, AC, heating, WiFi, and a washing machine/dryer for your convenience and 2 parking spaces with covered carport. Boat slips can be reserved for additional fee, if available. brbrREELaxation is within walking distance to several waterfront restaurants, Theatre of the Sea is around the corner, Robbie's is just up the road to hand feed the tarpon and Key West is within driving distance of a day trip. Located at mile marker 85, on the ocean side, you have so many options that are very easily accessible. Islamorada is a fisherman's dream with the back country water and the gulf stream each just a short boat ride away. Catch pelagic species like a tuna, sailfish, marlin, mahi or wahoo in the morning and close the day out in the back country with a tarpon, bonefish, trout, redfish, snook or snapper.brbrREELaxation is our only vacation rental and with an extensive background in customer service, extraordinary guest service and helping to make lifetime memories are our goal. We look forward to assisting in any way we can and making your next Keys vacation an unforgettable one! brbrBook now and enjoy everything this fabulous house has to offer. Do not hesitate to reach out to us with any questions that you may have.

Bed

Bath

Sleeps

$432.17

/ Nightly

Private Vacation Home

Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way

Islamorada, Florida, United States

Village of Islamorada license #24-0369br131 Anglers Way, Islamorada, FLbrThis Villa has 2 bedrooms (one with king bed and the other with One QUEEN SIZE BED and pull out couch) and 2 full bathrooms located on the 2nd floor, both with private balcony's. Down stairs there is a half bath, a full kitchen with stainless steel appliances, granite counters, living/dining room, New tile floors, cable TV, Wi-Fi and open porch with seating.br2 bikes included in rate. Community kayaks and paddleboards are avail to use (just have to sign a waiver).brCall me for more information 305-240-0592.brbrThis oceanfront resort is a boutique complex of 52 homes inspired by Key West architecture that was built in 2007. Gated community, located off the Old Hwy at MM 86 in Islamorada. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. brBoat slips are available for rent (for additional fee)for up to 31' boat with a deep channel out to the Atlantic. Trailer storage is no longer available outside gate please ask for storage recommendations. Be at Alligator Light house or the Famous Islamorada (Holiday Isle) sandbar in minutes. Launch your kayak or paddle board from the private beachbrbrCome on down and put your toes in the sand. It's always better in the Florida Keys.Angler’s Reef is the perfect place for all fishing and diving enthusiasts. Islamorada is known as “The Sport fishing Capital of the World”. Water activities abound including: diving, snorkeling, Para sailing, kiteboarding, paddle boarding, kayaking, and more. You may even spot manatees at the marina. Fine dining and unique shops are within walking distance: Island Grill (Famous for their tuna nachos) serving breakfast, lunch and dinner oceanfront with live music. For late night entertainment, walk on over to Hog Heaven for a fun night of dancing. Also, within in walking distance is Theatre of the Sea, where you can watch a live dolphin show or even swim with the dolphins!

Bed

Bath

Sleeps

$353.15

/ Nightly

Private Vacation Home

Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.

Islamorada, Florida, United States

Welcome to island time at beautiful Anglers Reef, the perfect way to experience and relax in the Florida Keys. Our home, the Drop Off, is our little bit of island paradise. Anglers Reef is a village of 52 single-family homes in an exclusive gated community located at MM 85. Whether you are looking for a couples retreat or a family excursion, Anglers Reef provides the experience you are looking for. brbrACTIVITIES:brYou can take in the beauty of the island while walking or biking the quaint neighborhood streets and along the marina boardwalk. Return from your bike ride to take a refreshing dip in our temperature controlled pool with beautiful views of the Atlantic Ocean. At one of the two beaches, enjoy complimentary paddle boards and kayaks, which you can use to venture to the nearby sandbar or to fish or investigate the mangrove lined shoreline. Plus, there are many shops and premier restaurants with in walking distance.br brBOATING AND FISHING: brIslamorada is appropriately referred to as The Sport Fishing Capital of the World as world class fishing opportunities surround the area. You can dock your boat in one of the private slips at the marina or charter a fishing excursion nearby for ultimate fishing opportunities. However, fishing is only one of the many water activities you can enjoy from Anglers Reef. There is world class site seeing, snorkeling, diving, and boating opportunities everywhere. Plus, you may even run into one of the local Manatees that frequent the marina. Please contact property owner for boat slip rental information and rates. brbrHOUSE:brOur beautiful home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances, including gas BBQ. Open porches and balconies, rich hard wood floors, open plan dining area with ample seating, tasteful décor and fully furnished rooms. A truly unique place to stay in the keys, with an island paradise feel.

2

Bed

1

Bath

6

Sleeps

$2472.56

/ Nightly

Private Vacation Home

Caribee Beach House ~ Private Islamorada Beach Estate W/ Heated Pool & Dockage

Islamorada, Florida, United States

Welcome to Caribee Beach House!brbrDiscover the enchanting charm of Caribee Beach House, where the timeless allure of old-school Islamorada beautifully melds with stylish comforts. Tucked away in the heart of downtown Islamorada, this hidden gem offers an extraordinary retreat with 200 feet of private water frontage, a spacious 100-foot dock, and stunning views of Alligator Lighthouse.brbrBring your entire crew to this sprawling estate that boasts six bedrooms and five bathrooms, comfortably accommodating up to 14 guests. The fully equipped kitchen awaits your culinary inspiration, whether you're whipping up family favorites or cooking your fresh catch of the day!brbrStep outside to be mesmerized by sweeping ocean vistas that promise to take your breath away. The expansive yard, adorned with lush greenery and twinkling bistro lights, creates a magical ambiance perfect for unforgettable evenings. Jump into the stunning heated and chilled pool, complete with a baja shelf with loungers and umbrellas. brbrFor those looking to stay active, challenge your guests to a friendly match on your very own pickleball court that also doubles as a basketball court, or enjoy a round of mini putt on the custom putting green, adding a playful touch to your vacation! After the games, unwind around the fire pit on your private sandy beach for cozy bonfire memories. Your very own 100-foot dock is ideal for docking your boat, heading out for an early morning fishing trip, or taking a serene sunset cruise. Should you be craving adventure, kayaks, paddle boards, and bikes are available for rent, delivered directly to the property for your convenience.brbrbrIf you choose to explore beyond the beautiful grounds, you’ll find Lazy Days Restaurant within walking distance, offering exquisite seafood and breathtaking oceanfront dining. Also nearby is Bud N’ Mary’s Fishing Marina, home to the oldest and largest fishing fleet in the Florida Keys. Here, you can book off-shore and in-shore fishing charters or embark on eco-tours and diving adventures.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. brbrWe also offer daily housekeeping, pre arrival grocery shopping, and golf cart rentals to make your stay as easy and enjoyable as possible.brbrThis property has a rich history, established in the 1950s, and has been lovingly revitalized to preserve its eclectic charm while enhancing its captivating grandeur. Your unforgettable escape awaits at Caribee Beach House! brbrAs part of nature’s vibrant tapestry, Sargassum seaweed may occasionally collect along the shores of the Florida Keys, including Islamorada. This natural phenomenon supports a thriving marine ecosystem, serving as a nursery for sea life and enriching the local environment.brbrCheck-in must be on a weekday. Weekend arrivals (Saturday or Sunday) start at $18,000/week plus taxes and fees. Prices and availability are subject to change without notice. Contact Coastal Vacation Rentals of the Florida Keys to confirm pricing and availability. Holiday weeks may incur peak pricing without notice.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.brbrVacation Rental License: 26-0205

Bed

Bath

Sleeps

$691.09

/ Nightly

Private Vacation Home

4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL

Islamorada, Florida, United States

Beautiful 4-bedroom, 3.5 bath home in Angler's Reef. Located at MM85, this tastefully decorated, open floor plan features a newly renovated gourmet kitchen including all of the amenities you’ll need for a perfect stay – updated appliances, quartz countertops and breakfast bar. Enjoy viewing some of the local artwork as you stroll throughout the home. We pride our home for hosting large groups and the newly added large sectional pulls out as additional sleeping space. A queen bedroom with en-suite bathroom is conveniently located on the first floor. There is also a stylish powder bathroom on the first floor off the kitchen and living area. The 8-person dining table is a perfect space to play cards and enjoy meals with your friends and family, while the kitchen island seats 5 people. A console table off the kitchen offers all the essential openers, koozies, martini shaker and plenty of games for a fun vacation! brbrThe porch off the family room offers ocean views, 2 comfortable chairs w/side table, an outdoor dining table seating 4-people and a grill. brbrThe second floor includes 3 bedrooms. Upstairs, the master bedroom features a four-poster king bed, en-suite bathroom with double sinks and an updated shower with bench. The master bedroom opens up to its own private covered porch with spectacular views of the ocean, 2 sofa lounge and 3 club chairs. The two upstairs bedrooms offer queen beds with a partial ocean view. There’s a full bathroom located between these two rooms. You’ll conveniently find a laundry closet with washer and dryer in the upstairs hallway that also offers a steamer and iron. All bedrooms include TV’s and wireless internet service provided. brbrThis rental includes boat slip #14, which can accommodate boats up to 31 feet in length. Angler’s Reef is a wonderfully maintained and gated community in Islamorada, the fishing capital of the world. In Islamorada you can swim with dolphins, go dive the reefs, sport fish or just simply enjoy the salt-water life and great restaurants.

4

Bed

3

Bath

8

Sleeps

$210.49

/ Nightly

Private Vacation Home

Charming 2 bedroom townhome at Executive Bay Club!

Islamorada, Florida, United States

Your chance to experience one of Islamorada's most sought-after communities has arrived! Brand new to the rental pool, this beautifully renovated townhome in Executive Bay Club (Unit C3) is the perfect escape for the winter season.brThe Owners have recently purchased and are in the process of refurnishing with all-new coastal-chic décor — photos coming soon! You'll love the modern updates, bright open spaces, and resort-style amenities.brEBC has it all: a newly refreshed pool and lounge area (looking AMAZING!), tennis and pickleball courts, and a stunning clubhouse overlooking the bay.brNow booking for the winter season — come enjoy the relaxed, island lifestyle at Executive Bay Club, where every day feels like vacation.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.

2

Bed

2

Bath

4

Sleeps

$574.56

/ Nightly

Private Vacation Home

Luxury 3/3·Secret Speakeasy·BBQ Patio·Dock·Pool

Islamorada, Florida, United States

Imagine: morning coffee on the balcony, ocean breeze in your hair, then a night in your own hidden speakeasy with karaoke and cocktails. Turtle Cove is Islamorada's most unique 3-bed, 3-bath retreat — luxury linens, 3 private ensuite baths, pool, dock, paddleboards, and bikes included. The Keys trip your group will never forget. Check availability now.brbrOnly at Turtle CovebrAmenities no other vacation rental in Islamorada offersbrbr- Private speakeasy lounge hidden on Level 1 — bar tops, mood lighting, and a vibe unlike anything else in the Keysbr- Karaoke stage — yes, a real stage. Belt your heart out after the kids go to bedbr- High-end game room: shuffleboard, air hockey, and corn hole steps from the patiobr- Private BBQ patio with al fresco dining and fire pit — your own outdoor living roombr- EV charging included — one of the only Islamorada rentals with a dedicated chargerbrbrBedrooms — luxury bedding & private ensuite in every roombr3 bedrooms · 3 ensuite baths · sleeps 8 · no shared bathroomsbrbr- Every bedroom has its own private ensuite bathroombr— no sharing, no waiting, no compromise. Each guest has their own space from the moment they arrive.br- Luxury linens on every bed — hotel-quality sheets, plush pillows, and premium duvet sets so you wake up rested and ready for an adventure-filled daybr- Primary king suite (Level 3): king bed dressed in premium linens · private ensuite bath · balcony with partial water views and ocean breezebr- Double-queen bedroom (Level 3): two queen beds with luxury bedding · private ensuite bath — perfect for kids, a second couple, or friends sharing a roombr- Queen bedroom (Level 2): queen bed with premium bedding · private ensuite bathbr- In-unit washer/dryer — pack light, leave fresh, laundry supplies providedbrbrWater, sun & adventurebrEverything included — no rentals, no extra feesbrbr- Partial ocean views from multiple balconies — catch the sunrise with your morning coffeebr- Dock access for boats up to 26 ft (first-come, first-served — ask us to confirm availability)br- Community pool steps from your doorbr- 2 paddleboards included — launch straight from the propertybr- 4 bikes ready to ride — explore the island car-freebr- Private fishing lessons available as a bookable add-onbrbrThe layoutbr3 bedrooms · 3 ensuite baths · sleeps 8brbr- Level 1: Private speakeasy · karaoke stage · games · BBQ patio with outdoor seating · garage gym · paddleboards & bikesbr- Level 2: Full kitchen · family room · balcony with dining · queen bedroom with ensuite bathbr- Level 3: Primary king suite with ensuite · double-queen bedroom with ensuite · luxury bedding throughout · in-unit laundry · balcony with partial water views & ocean breezebrbrWhy Islamorada brStill deciding where in the Keys to stay Here's why this is the sweet spotbrbr- The Sportfishing Capital of the World — world-class fishing, diving, and snorkeling right outside your doorbr- Perfectly positioned between Miami/Fort Lauderdale and Key West — the Upper Keys sweet spotbr- Freebee on-demand rides: Free electric rideshare (Tesla Model X) runs 7am–midnight daily throughout the village — get to dinner, bars, and beaches without moving your car free of charge (tips encouraged)br- Fly in by seaplane: Tropic Ocean Airways announced charter seaplane service from Fort Lauderdale direct to the Florida Keys — skip the traffic and arrive in stylebr- Walk or bike to top restaurants, beach bars, Anne's Beach, and Robbie's Marinabr- Gated Peaceful Palms community — private, secure, and beautifully maintainedbrbrGood to know before you bookbrPolicies, access & licensingbrbr- Smart lock self check-in — your personalized code arrives before arrivalbr- 1 dedicated parking spot directly in front of the unitbr- Dock space available on a first-come, first-served basis for boats 26 ft and under — contact us to confirm availability or get recommendations for nearby dockagebr- A rental agreement is required at booking to confirm terms and conditionsbr- Exterior security camera on property for your peace of mindbr- FL DBPR License: DWE5405520 · Islamorada Village License: 26-5090

Bed

Bath

Sleeps

$184.27

/ Nightly

Private Vacation Home

Classic 2 bedroom, 2 Bath Islamorada Home with Dockage

Islamorada, Florida, United States

** 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.

2

Bed

2

Bath

4

Sleeps

$1321.88

/ Nightly

Private Vacation Home

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Islamorada, Florida, United States

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

Bed

4

Bath

10

Sleeps

$2382.59

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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.

Bed

Bath

Sleeps

$759.45

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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

3

Bed

2

Bath

6

Sleeps

$191.72

/ Nightly

Private Vacation Home

Quaint Islamorada Cottage with Unbeatable Location

Islamorada, Florida, United States

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

Bed

Bath

Sleeps

$667.11

/ Nightly

Private Vacation Home

Luxurious Caribbean 2 Bedroom 2 Bath Home

Islamorada, Florida, United States

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

Bed

Bath

Sleeps

$458.9

/ Nightly

Private Vacation Home

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

Islamorada, Florida, United States

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.

2

Bed

2

Bath

4

Sleeps

Vacation Home Rentals By Owner In Islamorada, FL

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$759.45

$191.72

$667.11

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