Holiday rentals in Islamorada

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Top-rated holiday rentals in Islamorada

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Guest favourite

Cottage in Islamorada

4.95 out of 5 average rating, 41 reviews

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

27 Sep – 4 Oct

₹36,682 per night

Guest favourite

Home in Islamorada

5.0 out of 5 average rating, 12 reviews

Angler's Reef Gem in Islamorada!

Welcome to 128 Anglers Way: "Morada Daydreaming". This house has 2 bedrooms upstairs, each with its own full bath and private balcony. A washer/dryer combo is conveniently located upstairs. The main level open floor plan features peek a boo ocean views. It also contains a half bath and a fully stocked kitchen. An outdoor seating area and gas grill is provided. Includes 2 assigned parking spaces. Angler's Reef is a premier resort style community with a heated pool, kayaks, and paddle boards.

25 Jan – 1 Feb

₹35,158 per night

Guest favourite

Home in Islamorada

4.94 out of 5 average rating, 18 reviews

3 Lux Ensuites Walk/Boat Island! - Villa Plátano

Dive into the heart of Islamorada and COUPLES Imagine: THREE MASTER BEDROOMS, so no squabbles over only 1 Master! This 2017 townhome promises restful nights and lively marine filled mornings. From your balcony, salute serenity; Dockside bid sunsets a farewell or mingle with manatees and lobsters. A stroll away: world-class dining, boutiques, bars or a Paddleboard escapade. Welcome to bayside luxury with a splash of fun! Explore the community & nearby libations. Your tranquil Bayside haven awaits

29 Mar – 5 Apr

₹48,589 per night

Guest favourite

Guest suite in Marathon

4.98 out of 5 average rating, 186 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

30 Jul – 6 Aug

₹18,486 per night

Guest favourite

Holiday home in Key Largo

4.99 out of 5 average rating, 145 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

6–13 Sep

₹17,219 per night

Superhost

Cottage in Islamorada

4.81 out of 5 average rating, 143 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

28 Sep – 5 Oct

₹15,853 per night

Guest favourite

Home in Islamorada

4.97 out of 5 average rating, 167 reviews

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

7–14 Sep

₹22,417 per night

Guest favourite

Boat in Islamorada

4.92 out of 5 average rating, 327 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

6–13 Sep

₹15,915 per night

Guest favourite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 84 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

17–24 Sep

₹15,585 per night

Guest favourite

Flat in Tavernier

5.0 out of 5 average rating, 15 reviews

Beautiful condo with a balcony

Newly Renovated Beach Décor unit! Breathtaking views of the protected Florida Keys mangroves. Heated Olympic size pool/jacuzzi with fully equipped bar and bartender. Tennis courts recently renovated. Walking paths through the Florida Keys protected mangroves. Onsite marina, with beach, gazebo, dockage ramp. Restaurant with ocean views. Snorkeling and kayak on the premises. Walk to the end of the pier and take in the ocean breeze and watch the boats sail by.

28 Jul – 4 Aug

₹14,865 per night

Guest favourite

Home in Marathon

4.96 out of 5 average rating, 125 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

29 Sep – 6 Oct

₹28,027 per night

Guest favourite

Cottage in Islamorada

4.97 out of 5 average rating, 66 reviews

Key Lime Cottage 2br 1ba w/pool

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

17–24 Oct

₹32,625 per night