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Holiday rentals in Islamorada

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Top-rated holiday rentals in Islamorada

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Guest favourite
The eco-friendly two-story River Queen vessel is anchored in a calm harbor, showcasing a modern design. The structure features large windows and a rooftop terrace, with a wind turbine on the left. The surrounding landscape includes lush greenery, complementing the serene water view.
Boat in Tavernier
4.91 out of 5 average rating, 384 reviews

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Top guest favourite
A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.
Home in Key Largo
4.98 out of 5 average rating, 221 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Top guest favourite
The exterior of the cottage features a vibrant mural adorned with large floral designs, complemented by a light blue roof and shutters. Surrounded by lush greenery, the property sits on a textured gravel area under a clear blue sky.
Cottage in Islamorada
4.96 out of 5 average rating, 55 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage with Dockage. Short walk to world famous Lorelei for sunset celebrations. Great location for kayaking & paddleboarding. Custom length of stays can be arranged if booking a sandbar/fishing charter with our family. The fishing cottage built in the 1940s is not fancy, as photos show, but in the heart of Islamorada! Dockage available for additional $25 per night fee not included in nightly rate. Free trailer storage on site. Pet friendly :) 1 pet under 20 lb $150 fee.

Top guest favourite
A private beach area is visible, featuring soft white sand and arranged lounge chairs facing the calm ocean. Lush greenery lines the shore, with a small tree providing shade. In the background, a wooden pier extends into the water under a partly cloudy sky.
Apartment in Tavernier
4.9 out of 5 average rating, 306 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Guest favourite
A sandy beach area features numerous lounge chairs arranged in rows, each with a blue slatted design. In the background, a wooden pier extends over the water, surrounded by trees and calm waves under a clear sky.
Apartment in Tavernier
4.89 out of 5 average rating, 155 reviews

1BR - Key Largo Sun & Sand Hideaway

Welcome to Key Largo Sun & Sand Hideaway, where relaxation awaits in the beautiful Florida Keys. Our fully equipped one-bed, one-bath suite is the ideal destination for your next vacation. Nestled within an oceanfront resort, you'll enjoy access to a private beach, marina and other amenities. Indulge in a serene coastal experience just minutes away from restaurants, shopping, and other exciting water activities. Unwind, rejuvenate, and create unforgettable memories in this tropical paradise.

Top guest favourite
The living area features a comfortable light blue sofa and a glass-top coffee table, complemented by tropical-themed decor. A ceiling fan circulates air above, while a kitchen bar with high chairs is visible in the background. Natural light enters through multiple windows, enhancing the welcoming atmosphere.
Home in Islamorada
4.97 out of 5 average rating, 205 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.

Top guest favourite
Vibrant bougainvillea flowers in shades of pink and deep red create a lush display against the greenery. The dense foliage adds a natural texture, while drops of water may suggest recent rainfall, enhancing the overall freshness of the scene.
Guest house in Key Largo
4.94 out of 5 average rating, 189 reviews

Seaside Bungalow

Very private entire Cottage brand new walking distance to world famous Tiki Bar jet ski rentals kayaks Extremely private surrounded by exotic flowers and orchids.Less than 2 miles from Baker's Cay and close to the Key Largo and Islamorada wedding venues. We have a fully stocked home size kitchen. All the condiments coffee creamers sugar ketchup mustard etc. Giant stone shower with shampoos and conditioner and plenty of plush towels. Beach towels and chairs as well as 2 bicycles.

Guest favourite
The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.
Boat in Islamorada
4.93 out of 5 average rating, 368 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.

Guest favourite
Apartment in Tavernier
4.91 out of 5 average rating, 112 reviews

Blue Haven Key Largo | Ocean Pointe 1315

Tastefully decorated and newly renovated 2 Bedroom & 2 Bathroom Condo with a wonderful view of Florida Keys Nature. Relax and escape to this beautiful getaway in the heart of Tavernier, ideally located between Key Largo & Islamorada. The property itself has amenities galore: sparkling pool with hot tub and newly re opened POOL BAR, boat ramp and marina, tennis courts which convert into pickle ball courts, beach with pier, free parking and charcoal grills to cook your catch!

Guest favourite
Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.
Villa in Marathon
4.9 out of 5 average rating, 472 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Top guest favourite
A serene pool area is surrounded by lush tropical landscaping and palm trees. Lounge chairs are positioned around the pool, along with blue umbrellas providing shade. The clear water sparkles under the bright sun, creating an inviting space for relaxation.
Cottage in Islamorada
4.97 out of 5 average rating, 129 reviews

2br/1ba w heated pool, 1 mile to robbies marina

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!

Superhost
A spacious living area features a large sectional sofa adorned with decorative cushions. Natural light filters through the plantation shutters on the windows, illuminating the warm wooden floor and white walls. A modern light fixture hangs from the ceiling, adding a sleek touch.
Guest house in Key Largo
4.89 out of 5 average rating, 267 reviews

SaltSpray Bungalow Oceanside, 1 bedroom

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

Popular amenities for Islamorada holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Islamorada's top sights

Cheeca Lodge & Spa

12 locals recommend

Robbies Marina Of Islamorada

279 locals recommend

Theater of the Sea

228 locals recommend

Other great holiday rentals in Islamorada

Top guest favourite
Home in Islamorada
5 out of 5 average rating, 6 reviews

Off The Charts-Waterfront Tiki Bar & Private Dock

Top guest favourite
Home in Islamorada
5 out of 5 average rating, 9 reviews

OceanView 2/2.5 w Beach Pool & Marina Islamorada

Top guest favourite
A two-story yellow house is seen framed by lush greenery and palm trees. A covered carport is visible, providing shade, while multiple windows allow natural light into the home. The well-maintained exterior blends with the serene landscaping surrounding the property.
Home in Islamorada
4.94 out of 5 average rating, 47 reviews

Beautiful Anglers Reef - 2/2.5 - Pool+Marina+Beach

Top guest favourite
A serene outdoor seating area features two woven chairs facing a sunset over the bay. A small metallic table sits between the chairs, and palm trees are visible in the distance, framing the tranquil water view.
Townhouse in Islamorada
4.98 out of 5 average rating, 84 reviews

Bayside Townhome in Islamorada with Boat Slip

A serene sunset is visible over the Atlantic Ocean, with warm orange and yellow hues blending into the sky. A sailboat is seen on the horizon, adding a touch of tranquility to the scenic view.
Apartment in Tavernier
4.84 out of 5 average rating, 302 reviews

Condo in the Keys, Peaceful ocean view retreat!

A floating home is anchored in clear waters, surrounded by lush greenery. The structure is highlighted by solar panels on the roof and a spacious white deck, featuring railings that outline the edges. Bright blue skies and distant mangroves create a serene backdrop.
Houseboat in Islamorada
4.68 out of 5 average rating, 31 reviews

Perfect escape to the ocean

Guest favourite
Two yellow Adirondack chairs are situated on the sandy shore, facing a calm bay. Lush trees frame the scene, providing shade. A dock with boats is visible in the distance, under a clear blue sky dotted with a few clouds.
Home in Key Largo
4.91 out of 5 average rating, 68 reviews

Treetops

Guest favourite
A serene waterfront view is presented, featuring several white Adirondack chairs positioned along a sandy beach. The calm water reflects a clear blue sky, with lush greenery visible in the background, creating an inviting space for relaxation.
Home in Islamorada
4.85 out of 5 average rating, 61 reviews

Oceanfront community 114 Anglers Reef Islamorada

When is the best time to visit Islamorada?

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Avg. price$413 SGD$477 SGD$487 SGD$417 SGD$492 SGD$411 SGD$422 SGD$413 SGD$390 SGD$374 SGD$389 SGD$418 SGD
Avg. temp20°C22°C23°C25°C27°C28°C29°C29°C28°C27°C24°C22°C

Frequently Asked Questions

  • What are the best places to stay in Islamorada?

    Islamorada has a range of guesthouses, private rentals, and waterfront cottages, especially around the marina and near the coastline. Many visitors explore areas close to the water to enjoy snorkeling, local restaurants, and sunset views.

  • What are the best things to do in Islamorada with kids?

    Families frequently enjoy exploring marine life exhibits, interactive aquariums, and sandy beaches. Guided snorkeling tours and paddleboard rentals are also popular ways for kids to discover sea creatures in shallow, clear waters.

  • What are some of the best things to do in Islamorada?

    You can explore local museums, try sport fishing, and visit art galleries. Many visitors also join snorkeling or diving excursions to see vibrant reefs, or enjoy waterfront dining with fresh seafood.

  • How is the weather in Islamorada?

    Islamorada has a tropical climate with winter temperatures around 61–78°F (16–26°C) and summers getting up to 91°F (33°C). Rain is more frequent in late spring and summer, so packing layers and sun protection is often recommended.

  • When is the best time to visit Islamorada?

    Late winter through spring is often suggested for mild temperatures and lower rainfall, making it comfortable for beach activities and outdoor exploration. Summer brings warmer days and more rainfall, along with a vibrant fishing season.

  • What are the best places to visit in Islamorada?

    Islamorada has museums focused on diving and local history, as well as marina areas with waterfront views. Explore artisan shops, marine life centers, and sculpture gardens for a taste of the area's culture.

  • What are some hiking trails in Islamorada?

    You can walk shaded loops through tropical hammock preserves or follow nature trails in local parks. Paths wind past native plants, birdwatching spots, and occasional interpretive signs about the habitat.

  • What are some family activities we can do in Islamorada?

    Families often explore touch tanks at marine centers, kayak calm waters, or join guided eco-tours. Beach picnics and shallow snorkeling are also frequently suggested for groups with children.

  • What are some of the best day trip ideas from Islamorada?

    Many visitors plan outings to nearby state parks, animal sanctuaries, or botanical gardens. Guided boat tours, art village visits, and trips to other islands in the Keys are also frequently suggested.

  • Are there any pet friendly accommodations available in Islamorada?

    Islamorada has pet-friendly rentals, including cottages and beachside homes. Some local parks and waterfront paths also welcome dogs on a leash, making it easier to enjoy the outdoors with your pet.

  • What are some local tips for visiting Islamorada?

    Pack reef-safe sunscreen, as preservation of marine life is prioritized. Local eateries get busy at sunset, and water shoes can help when exploring rocky shorelines or tide pools.

  • What is Islamorada known for?

    Islamorada is known for sport fishing, vibrant coral reefs, and a relaxed Florida Keys atmosphere. Visitors frequently highlight its clear waters, seafood cuisine, and picturesque sunsets.

  • What are the best hidden gems to explore in Islamorada?

    Look for small artists’ studios, tucked-away hammocks with native flora, or local preserves not always on tourist maps. Independent galleries and small historic sites often give a different perspective on the area.

  • What are the best foods to try in Islamorada?

    Islamorada is known for locally caught seafood like yellowtail snapper, stone crab, and Florida lobster. Key lime pie and conch fritters are frequently suggested treats, reflecting flavors of the region.

  • What should I bring for a trip to Islamorada?

    Bring breathable clothing, swimwear, reef-safe sunscreen, and a sun hat for outdoor comfort. Water shoes and a reusable water bottle are helpful for exploring beaches and staying hydrated.

  • What is the nightlife in Islamorada like?

    Nightlife in Islamorada is relaxed, with locally owned bars, seafood spots, and live music venues by the water. Evenings often feature acoustic performances, tropical cocktails, and sunset views.

  • What are the most popular events or festivals in Islamorada?

    Islamorada hosts annual seafood festivals and sport fishing tournaments, with some events timed around winter and spring. Local art walks and culinary celebrations also draw visitors during peak travel periods.

  • Are there family friendly vacation rentals in Islamorada?

    Family-friendly rentals are available throughout Islamorada, including waterfront homes and cottages with outdoor spaces. Many provide convenient access to beaches, playgrounds, and marine activities.

Quick stats about holiday rentals in Islamorada

  • Total holiday rentals

    Explore 800 holiday rentals in Islamorada

  • Nightly prices starting at

    Islamorada holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 8,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    570 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 400 rentals that welcome pets

  • Holiday rentals with a pool

    620 properties feature pools

  • Rentals with dedicated workspaces

    460 properties have a dedicated workspace

  • Wifi availability

    790 of Islamorada holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Beachfront and Gym across Islamorada rentals

  • 4.7 Average rating

    Islamorada stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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