$4,290
Available: Right Now
Listed: 16/05/2024
Islamorada, FL, 33070
Welcome to the Cottage on Pearl!This brand new 3 bedroom 2 bathroom home is set up perfectly for your next Keys getaway. The fully stocked gourmet kitchen is ready for you to prepare your favorite home cooked meals and the open living plan ensure...
$18,000
Available: Right Now
Listed: 17/05/2024
Islamorada, FL
The Garden View Cottage is one of three homes at Mermaid's Bay Boutique Estate. This private waterfront oasis sprawls 3.5 acres in the heart of Islamorada, just moments away from all of the top attractions and restaurants. The estate features over 30...
$14,250
Available: Right Now
Listed: 16/05/2024
Islamorada, FL, 33070
There is something for everyone in your group within reach. If you are a boater, the open bay is only a moment's boat ride and the ocean is a quick trip through Tavernier Creek. The shops and restaurants of Islandmorada are just a short drive or bike...
$9,000
Available: Right Now
Listed: 13/05/2024
Islamorada, FL
Indulge in the allure of the Florida Keys with our Caribbean retreat nestled in the heart of Islamorada. Immerse yourself in a 2-bedroom, 2-private bath with Queen beds comfortably accommodating up to 4 guests.Experience the vibrant ambiance of o...
$4,920
Available: Right Now
Listed: 16/05/2024
Islamorada, FL, 33070
This beautiful apartment is new to the rental market and recently fully remodeled. Modern, clean with a stunning direct open water bay view. Open concept kitchen with new stainless steel appliances. 2 beds - a Queen and a twin and a new queen pull ou...
$16,110
Available: Right Now
Listed: 17/05/2024
Islamorada, FL
May and June 2024 Special $3400 weekly!!....Oceanfront Maison Matecumbe #303 - Maison Matecumbe is a premier gated oceanfront complex in the heart of Islamorada. This prime oceanfront three bedroom, two bath flat unit offers an open concept living an...
$13,440
Available: Right Now
Listed: 16/05/2024
Islamorada, FL
Little Bay Lower Level - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rent...
$6,960
Available: Right Now
Listed: 16/05/2024
Islamorada, FL, 33070
Indulge in the serene scenery, at our charming ocean veiw condo at Ocean Pointe Suites. Ideal for couples, solo & budget travelers, Key West Road Trippers, Snowbirds, Sea-foodies, Divers, Snorkelers & Anglers. Its central location places you within a...
$3,150
Available: Right Now
Listed: 17/05/2024
Islamorada, FL, 33070
Please note: We require a 28 day minimum rental.Located on the Ocean at mile marker 90 on Plantation Key, in Islamorada, we have beautiful sunrises from the balcony and gorgeous sunsets from the rooftop. Peaceful and away from the highway. Sleeps...
$21,600
Available: Right Now
Listed: 16/05/2024
Islamorada, FL, 33070
Please email with any and all questions !Welcome to Flipper’s House with breathtaking Atlantic Ocean views and access to world class fishing, snorkeling and diving. Enjoy beautiful sunrises from this large ocean front property with 63 feet...
$9,750
Available: Right Now
Listed: 17/05/2024
Islamorada, FL
Stay comfortably in Islamorada at this 3-bedroom house. This phenomenal property offers a tranquil escape for guests seeking a cool and relaxing vacation. With 2 king beds, 1 twin bed, and 1 queen bed, you'll have plenty of space to unwind and rechar...
$9,000
Available: Right Now
Listed: 17/05/2024
Islamorada, FL, 33070
Come down and just relax in our beautiful vacation home in the Florida Keys. This house is located in Tavernier Florida, 60 miles south of Miami, and just north of Islamorada. Key West is only a 90 mile drive.Bring or rent a boat and dock it behi...
$12,750
Available: Right Now
Listed: 16/05/2024
Islamorada, FL
This tropical oasis includes a heated pool and dock that reaches out onto a protected lagoon that opens into the Florida Bay.There are 3 bedrooms and two bathrooms upstairs, and a downstairs bedroom suite with private bathroom that opens onto the...
$18,750
Available: Right Now
Listed: 16/05/2024
Islamorada, FL
Minimum 28 day stay. Dreaming of a FL Keys vacation where you can boat, fish, dive, snorkel or stay home and swim in your own private heated pool? This is it! The charm of this home begins as you approach this upscale property with tropical lands...
$9,180
Available: Right Now
Listed: 16/05/2024
Islamorada, FL
Large 3/2 with ground level carport. Lagoon side screened porch 50' x 10'. Terrace on Ocean side is open. Boat access on Gulf side fishing and snorkeling, you can be in the ocean quickly. WiFi internet, 5 large screen TVs all with internet access. Sp...
$7,200
Available: Right Now
Listed: 16/05/2024
Islamorada, FL, 33070
With thoughtful and creative touches both inside and out mixed with a keen attention to the smallest of details, this oceanfront condo exudes a breezy sense of magic, whimsy and laid back Florida Keys style. Upon entering the home you’ll be greet...
$10,800
Available: Right Now
Listed: 16/05/2024
Islamorada, FL, 33070
134 Tequesta Street - Get ready to dive into your Islamorada Winter Retreat! Move in ready today!This beautiful three-bedroom three bath pool home is located at mile marker 89 on a deep-water canal. Bring your boat (20' or less only please) and f...
$4,500
Available: Right Now
Listed: 16/05/2024
Islamorada, FL
Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this listing. Contact us for our ...
$11,250
Available: Right Now
Listed: 17/05/2024
Islamorada, FL
Welcome to paradise! Completely remodeled and immaculately maintained... Bungalow Blue is nestled away in the quiet quaint Shady Palms community of Islamorada MM76, Lower Matacumbe.If you're looking to relax and unwind while also being in close p...
$37,950
Available: Right Now
Listed: 16/05/2024
Islamorada, FL
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incred...
$5,250
Available: Right Now
Listed: 16/05/2024
Islamorada, FL
Vacation like a local! This charming 2 bedroom, 2 bath home is located in one of Islamorada’s quaintest and quietest neighborhoods of just 40 residences.This home is bright and tropically decorated. The master suite features a private bath with s...
$4,290
Available: Right Now
Listed: 16/05/2024
Islamorada, FL
Gorgeous 2 bedroom 2 bath condo all on one floor with Heated pool, dock for fishing, and outdoor balcony. Gated community makes it a perfect getaway for a family for 4 but sleeps 6 to accommodate any short term visitors. Inside our home, you w...