Vacation Condo Rentals By Owner In Islamorada, FL

Showing 20 Of 77 Vacation Rentals

$202.84

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

Islamorada, Florida, United States

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.

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Bath

Sleeps

Exceptional(22)

$440.42

/ Nightly

Condo

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

Islamorada, Florida, United States

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.

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Bath

Sleeps

Exceptional(13)

$229.73

/ Nightly

Condo

Escape to Paradise in Islamorada!

Islamorada, Florida, United States

Welcome to your perfect family-friendly getaway in the heart of Islamorada, Florida! Nestled between the sun-soaked shores of Founders Park & Beach and the delicious dining at Marker 88 Seafood Restaurant, this charming townhome is your gateway to fun and relaxation. With boat rentals, live entertainment, nature visitor centers, shopping, and endless attractions just around the corner, there’s always something exciting to do!brbrPerfect for Extended Stays – 30 Day MinimumbrbrThis spacious, newly renovated 2-bedroom, 1.5-bathroom townhome comfortably sleeps up to 11 people, making it ideal for families or groups. Conveniently located just 90 minutes from Miami International Airport, our home is centrally positioned within the complex for easy access to tennis courts, a sparkling swimming pool, a welcoming clubhouse, and a private beach. For boating enthusiasts, there's a newly renovated boat dock complete with a full-size fish cleaning station—perfect for a day out on the water and bringing back your fresh catch! Please note: Overnight docking is not allowed; the dock is for pick-up and drop-off only.brbrFully equipped with fun vacation essentials, the home includes a margarita blender for refreshing poolside drinks, a beverage fridge to keep your favorite refreshments cool, and a backyard BBQ grill perfect for family cookouts. You’ll feel right at home with these amenities, along with the fresh, modern updates throughout, from the chic bathrooms and cozy bedrooms to the new flooring.brbrPlease Note: The townhome features a spiral staircase, which may be challenging for those who have difficulty with stairs. Additionally, for the comfort and safety of all our guests, we have a no-pets policy.brbrWhether you’re looking to explore the wonders of Islamorada, enjoy a boating adventure, or simply relax by the pool, this townhome is the perfect spot for a family adventure! Book your stay today and start making memories in paradise!

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Bath

Sleeps

$207.19

/ Nightly

Condo

Papa Joe's Waterfront - Oceansuite 302

Islamorada, Florida, United States

Discover Tranquil Luxury at Our Waterfront SuitesbrbrIndulge in the epitome of waterfront living with our two exquisite 1-bedroom, 1.5-bath penthouse suites nestled within the heart of Islamorada, atop the prestigious Papa Joe’s Waterfront establishment.brbrEscape to a world of luxury and serenity at our waterfront fish camp suites. Contact us today to reserve your slice of paradise and embark on a journey of unforgettable moments and cherished memories.brbrBest Sunset Views and Waterfront Views!brbrLocated on top of the world-famous Papa Joe's Waterfront, these condos are sure to make your stay memorable while in the Florida Keys. Conveniently located right in the heart of the keys we are just a short drive to Miami / Key West.brbrPublished rates apply to extended night stays with a minimum stay of 28 nights. If you want a short-term rental, we are happy to accommodate your request on a case-by-case basis, but please note that rates will be different.

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Bath

Sleeps

Exceptional(3)

$206.57

/ Nightly

Condo

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

Islamorada, Florida, United States

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!

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Bath

Sleeps

$141.34

/ Nightly

Condo

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

Islamorada, Florida, United States

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.

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Bath

Sleeps

$292.87

/ Nightly

Condo

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

Islamorada, Florida, United States

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.

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Bath

Sleeps

Exceptional(11)

$899.83

/ Nightly

Condo

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

Islamorada, Florida, United States

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.

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Bath

Sleeps

Exceptional(6)

$238.89

/ Nightly

Condo

Beachfront Villa w/ Pier & Pool

Islamorada, Florida, United States

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

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Bath

Sleeps

Exceptional(5)

$418.53

/ Nightly

Condo

Barefoot Bliss: Ground Floor Condo with Den & Dual Balconies

Islamorada, Florida, United States

This spacious suite offers comfort and convenience and is located on the ground floor with a pool and partial ocean views. The well-appointed kitchen features a full-sized fridge, stove, coffee maker, toaster, and all the essential dishes and silverware, making it easy to prepare meals. The inviting living room is furnished with a sofa bed and dining table, while the balcony lets you enjoy refreshing tropical breezes. A convenient bathroom completes the main living area.brbrThe tranquil bedroom offers a queen bed and access to a cozy den with a full-sized sleeper sofa, ideal for additional guests or a quiet reading nook. The bedroom also includes an ensuite bath, and the den opens onto a second balcony for more relaxation.brbrCaloosa Cove Resort and Marina boasts many amenities, including a heated pool, beach access, a General Store, and complimentary Wi-Fi. For those seeking adventure, the on-site marina offers Charter Boats and boat slip rentals for a nominal fee, making diving into world-class sport fishing and other aquatic activities easy.brbrGetting around is effortless with Caloosa's free transportation app, and the Caloosa KeyCard provides free access to Founders Park, a 25-acre paradise featuring sandy beaches, a saltwater swimming area, and ample space to unwind and explore.brPlease note: Guest passes to Founders Park do not include pool use.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

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Bath

Sleeps

Exceptional(8)

$416.2

/ Nightly

Condo

Anchor Here: Oceanfront 1BR Condo with Marina Access

Islamorada, Florida, United States

Immerse yourself in the tranquility of island living with this spacious first-floor pool-view suite, perfectly designed to accommodate up to 6 guests. Featuring 2 queen beds, a queen sofa sleeper, and 2 full bathrooms, this suite is an excellent choice for a memorable family getaway.brbrThe bedroom offers ultimate relaxation with two queen beds, an ensuite bathroom, and a private balcony, perfect for unwinding while soaking in the peaceful surroundings. brbrThe living area enhances the experience with a queen sofa bed, a compact yet fully equipped kitchen, a dining table for four, a second bathroom, and an additional balcony for extra space to enjoy the view.brbrAt Caloosa Cove Resort & Marina, guests can indulge in a variety of amenities. brRelax by the large heated pool with stunning ocean views, or enjoy friendly matches of Shuffleboard, Pickleball, Tennis, or Basketball. brbrFor a quieter escape, the small library provides a peaceful reading spot. Savor a delightful outdoor meal using the BBQ grills, perfect for family gatherings.brbrFor those eager to explore the water, the onsite marina offers boat slip rentals for a nominal fee, making it easy to set sail for a day of fishing or adventure on the crystal-clear waters of Islamorada.brbrThis suite blends comfort, leisure, and adventure, ensuring everything you need for a truly unforgettable island retreat!

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Bath

Sleeps

Exceptional(20)

$413.98

/ Nightly

Condo

Tropical Tranquility: Oceanview 1BR Suite on the Island

Islamorada, Florida, United States

Embrace the tranquility of island living in this spacious second-floor ocean-view suite, designed to accommodate up to 6 guests. With 2 queen beds, a queen sofa sleeper, and 2 full bathrooms, this suite is perfect for family getaways. brbrThe bedroom offers ultimate comfort with two queen-sized beds, an ensuite bathroom, and a private balcony where you can unwind while taking in the serene views. In the living area, enjoy a cozy queen sofa bed, a compact yet fully equipped kitchen, a dining table for four, a second bathroom, and an additional balcony for even more scenic views.brbrAt Caloosa Cove Resort & Marina, you will have access to a variety of fun amenities. Relax by the large heated pool with breathtaking ocean views, or enjoy friendly competition with Shuffleboard, Pickleball, Tennis, and Basketball. For those looking for a quiet escape, the small library is perfect for a peaceful read. BBQ grills are available for a delicious outdoor meal.brbrThe onsite marina offers boat slip rentals for aquatic enthusiasts for a nominal fee, making it easy to take your boat out for a day of adventure.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

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Bath

Sleeps

Exceptional(2)

$418.53

/ Nightly

Condo

Island Time Starts Here: Cozy Ground Floor Suite in Islamorada

Islamorada, Florida, United States

Start your day with coffee on your private patio, soaking in the fresh sea breeze as you plan your Florida Keys adventures. Relaxation is always within reach, whether you are basking on the private beach or enjoying a dip in the heated pool. For thrill-seekers, water activities and boat charters are just steps away.brbrThis spacious one-bedroom, two-bathroom suite features an equipped kitchen (no dishwasher), two queen beds, and a queen sleeper sofa. The open living area, with light wood tones, creates a calming retreat for up to six guests.brbrAt Caloosa Cove Resort, enjoy a heated swimming pool, beach access, and a General Store for your essentials. Our marina offers boat slip rentals for an additional fee, making it easy to explore the sparkling waters of Islamorada.brbrNote: This ground-floor unit does not include ocean views. Thank you for your understanding.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

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Bath

Sleeps

Exceptional(15)

$326.3

/ Nightly

Condo

Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views

Islamorada, Florida, United States

Experience the beauty of Islamorada in this spacious ground-floor studio designed to accommodate up to three guests. With stunning ocean views and cozy comforts, your tropical retreat awaits.brbrSuite Features:brQueen-Size Bed: Sink into comfort each night after a day of exploring or relaxing.brTwin Sleeper Sofa: Ideal for an additional guest or to curl up with a good book.brPrivate Patio: Step outside to enjoy the ocean breeze, vibrant sunsets, or your morning coffee surrounded by stunning views.brCompact Kitchenette: Prepare light meals with ease using the full-sized fridge, stove, and coffee maker. Dishes and silverware are provided, though there is no dishwasherbrbrResort Amenities:brAt Caloosa Cove Resort and Marina, we’re here to make your stay unforgettable:brbrHeated Pool: Lounge poolside or take a refreshing dip in our inviting heated pool.brBeach Access: Stroll along the soft sands or bask in the sun on our peaceful stretch of beach.brGeneral Store: Stock up on snacks, drinks, and vacation essentials.brFree Wi-Fi: Stay connected with complimentary high-speed internet throughout the resort.brCharter Boats and Marina: Dive into adventure with fishing charters or rent a boat to explore the turquoise waters.brDiscover Islamorada:brKnown as the Village of Islands, Islamorada is a paradise for relaxation and adventure:brWorld-Class Fishing: Experience why Islamorada is the Sport Fishing Capital of the World.brLocal Charm: Explore unique shops, mouthwatering restaurants, and local attractions.brFounders Park Access: Enjoy free entry to this 25-acre haven featuring sandy beaches, a saltwater swimming area, and plenty of space to unwind, courtesy of the Caloosa KeyCard.brPlease Note: Guest passes to Founders Park do not include pool use.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

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Bath

Sleeps

Exceptional(10)

$418.53

/ Nightly

Condo

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Islamorada, Florida, United States

Immerse yourself in the serenity of island life with this spacious second-floor pool-view suite thoughtfully designed to host up to 6 guests. It has 2 queen beds, a queen sofa sleeper, and 2 full bathrooms, so it's the perfect choice for family vacations.brbrThe bedroom provides exceptional comfort with two queen beds, an ensuite bathroom, and a private balcony, ideal for unwinding while enjoying peaceful views. The living area adds to the charm, offering a cozy queen sofa bed, a compact yet fully equipped kitchen, a dining table for four, a second bathroom, and an additional balcony for an even more relaxing space.brbrAt Caloosa Cove Resort & Marina, you will enjoy many exciting amenities. Lounge by the large heated pool overlooking the ocean or engage in friendly games of Shuffleboard, Pickleball, Tennis, or Basketball. For a quieter retreat, the small library provides a cozy corner for reading. Fire up the BBQ grills to savor a flavorful outdoor meal with loved ones.brbrBoating enthusiasts will appreciate the on-site marina, which offers convenient boat slip rentals for a nominal fee. This makes it easy to embark on a day of exploration or adventure on the water.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

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Bath

Sleeps

Exceptional(5)

$411.71

/ Nightly

Condo

Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access

Islamorada, Florida, United States

Welcome to your island retreat! This spacious ground-floor Den Suite offers the perfect blend of relaxation and fun, complete with all the comforts of home in the heart of the Florida Keys.brbrYour Suite Includes:brAn equipped kitchen with a full-sized fridge, stove, coffee maker, toaster, dishes, and silverware is ideal for whipping up a quick meal.brA cozy living room with a sofa bed, dining table, and a balcony to enjoy tropical breezes.brA serene bedroom with a queen bed, an ensuite bathroom, and access to a den featuring a full sleeper sofa, great for extra guests or a quiet reading nook.brA second balcony off the den for even more relaxation.brbrResort Highlights:brHeated pool for a refreshing dip.brBeach access to soak up the sun.brA General Store is available for your convenience.brOn-site marina with charter boats and boat slip rentals for aquatic adventures.brComplimentary Wi-Fi to stay connected.brbrLocal Perks:brExplore nearby attractions with Caloosa's free transportation app, and enjoy free access to Founders Park with your Caloosa KeyCard! This 25-acre gem features sandy beaches, a saltwater swimming area, and plenty of space to relax and play.brPlease note: Guest passes to Founders Park do not include free pool use.brbr**This ground-floor unit does not have a view.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

Bed

Bath

Sleeps

Exceptional(3)

$418.53

/ Nightly

Condo

Stay Salty: Keys Dreams 1BR Condo Steps from the Sand

Islamorada, Florida, United States

Discover the spacious comfort of our 1-bedroom, 2-bathroom suite, offering a tranquil haven for guests to unwind. Relax in the bedroom with two queen beds, an ensuite bathroom, and a private balcony for a peaceful retreat. The living area exudes warmth and hospitality, featuring a cozy queen sofa bed, a compact yet functional kitchen with a dining table for four, a second bathroom, and an additional balcony. While our property boasts an oceanfront location, please note that this unit does not have a water view. brbrAt Caloosa Cove Resort, guests are treated to breathtaking vistas, a welcoming heated swimming pool, a serene beachfront, a convenient General Store, boat slips, and exciting boat charters. With an abundance of activities just moments away, it's the perfect destination to unwind and fully immerse yourself in the enchanting ambiance of Islamorada.

Bed

Bath

Sleeps

Exceptional(4)

$331.83

/ Nightly

Condo

Second Floor Ocean View Studio – Gorgeous Waterfront Escape

Islamorada, Florida, United States

Experience the beauty of Islamorada in this spacious second-floor studio, thoughtfully designed to accommodate up to three guests. With breathtaking ocean views and all the comforts you need, your tropical retreat awaits.brbrSuite FeaturesbrQueen-Size Bed: Relax and recharge on a cozy queen bed, perfect after a day of adventure or lounging by the sea.brTwin Sleeper Sofa: Ideal for an additional guest or a cozy spot to unwind with a book.brPrivate Balcony: Step outside to take in the ocean breeze, vibrant sunsets, or your morning coffee amidst stunning views.brCompact Kitchenette: Easily prepare snacks or light meals with a full-sized fridge, stove, and coffee maker. Dishes and silverware are provided, but please note there is no dishwasher.br brResort AmenitiesbrAt Caloosa Cove Resort and Marina, you will find everything you need for a relaxing and unforgettable stay:brbrHeated Pool: Cool off or soak up the sun in our inviting, heated swimming pool.brBeach Access: Enjoy a peaceful stretch of sand perfect for sunbathing or leisurely strolls.brGeneral Store: Conveniently stock up on snacks, beverages, and essentials.brFree Wi-Fi: Stay connected with complimentary high-speed internet.brCharter Boats and Marina: Get adventurous with fishing charters or boat rentals to explore the pristine turquoise waters.brDiscover IslamoradabrKnown as the Village of Islands, Islamorada offers the perfect blend of relaxation and excitement:brbrWorld-Class Fishing: Discover why Islamorada is celebrated as the Sport Fishing Capital of the World.brLocal Charm: Explore one-of-a-kind shops, delicious restaurants, and unique attractions.brFounders Park Access: The Caloosa KeyCard provides free entry to this 25-acre paradise with sandy beaches, a saltwater swimming area, and plenty of space to relax and play.brPlease Note: Guest passes to Founders Park does not include use of the pool.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

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Bath

Sleeps

Exceptional(63)

$491.95

/ Nightly

Condo

Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

Islamorada, Florida, United States

1st I want to thank all our past guests for their great reviews.brBay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo has been decorated in Tommy Bahama style with a large living and dining area, including a wet bar. The kitchen is equipped for family cooking and has a writing desk for your convenience. The Master suite is very roomy and in suite bath with large jetted soaking tub and seperate shower and walkin closet. This bedroom has sliding glass doors leading out to the expanse screened in lanai overlooking the boat basin. Two guest bedrooms have Queen sized beds and are designed in a tropical motif. The living and dining areas also lead out to the screened in patio, where you can dine alfresco and watch the boats coming into the basin. There is a 30' boat slip included with electric and water, fish cleaning stations are setup by the dock. There is a locking storage area in the garage for you to put all of your boating gear or bikes. The storage area includes a freezer for your bait and catch. The facility includes tropical landscaping, a heated pool and spa, large gym with workout equipment and a club house. There are grills for you to use and the tennis and basketball courts are lighted. Rental license 24-261.

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Bath

Sleeps

Exceptional(15)

$350.38

/ Nightly

Condo

Islamorada 3/2 condo. Futura Yacht Club Dockage, swimming pool, sunsets

Islamorada, Florida, United States

Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit community with a 53 slip marina and accommodations available for that tranquil tropical getaway you've always imagined. brbrFutura Yacht Club is a gated community. This is a 4th floor condo with 3 bedrooms, 2 baths and a fantastic view of the Florida Bay. This condo is one of our nicest units with beautiful decor, a full kitchen with granite counter tops, barstool seating, living room, dining table for 6, and a balcony overlooking with stunning water views. Elevator building and community laundry located on each floor. brbrbrVacation Rental license #25-0426

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Vacation Condo Rentals By Owner In Islamorada, FL

$202.84

$440.42

$229.73

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Rent a place that suits your needs

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