
Holiday rentals in Islamorada
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Top-rated holiday rentals in Islamorada
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4. Cozy Waterfront Apartment in Key Largo!
Enjoy water front living in Key Largo! Watch the boats go by with fresh catch served daily at the local restaurants. See manatees, nurse sharks and fish swim by the canal all day. Dock your boat at the Pilot House Marina just down the street. Our unit is Modern, Spacious and Spotless with Private Parking, Fast Wifi, Netflix, Cold AC, Plush Pillows and a Cozy bed. We are on a main canal to open ocean. Near Rodriguez Key, Mosquito Bank, Christ of the Abyss and many sunken shipwrecks for exploring.

Turtle-By-The-Sea: the Best Deal in KCB!
A perfect get-away for couples or budget travelers, Turtle-by-the-Sea 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. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

Oceanfront Lookout Point w/two Kayaks & Deck
Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Romantic cozy peaceful Guesthouse beach Sunsets.
Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

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!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Beach House - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg
Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

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.

Toes in the Sand - 2 Bedroom Condo Sleeps 4
2-bedrooms, 2 full baths located on the 4th floor with ocean views. This condo has a beach, viewing pier, rentable boat slips, & boat trailer storage, café and a very large heated pool with a bar and gated entry with 24 hour security! Perfectly located between Key Largo and Islamorada, close to Pennekamp State Park, Harry Harris State Park, popular restaurants on the water, and the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer at your footsteps.

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.

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.

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!
Popular amenities for Islamorada holiday rentals
Stay near Islamorada's top sights
Other great holiday rentals in Islamorada

Florida Keys Oceanside Utopia

The Lookout #48 Full Ocean View Luxury Villa |

Islamorada house with best location. Lic # 24-0055

OceanView 2/2.5 w Beach Pool & Marina Islamorada

The Roseate House at Grassy Key Lic. #VACA-25-222

Hidden Gem Islamorada | 1st Floor

NEW! 4-Story Villa, Private Rooftop, Pool, Marina

Oceanview Escape
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $417 SGD | $482 SGD | $492 SGD | $421 SGD | $497 SGD | $415 SGD | $426 SGD | $417 SGD | $394 SGD | $384 SGD | $392 SGD | $441 SGD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°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 820 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 8,180 verified reviews to help you choose

Family-friendly holiday rentals
580 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 410 rentals that welcome pets

Holiday rentals with a pool
630 properties feature pools

Rentals with dedicated workspaces
460 properties have a dedicated workspace

Wifi availability
800 of Islamorada holiday rentals include wifi access

Popular amenities for guests
Guests love Self check-in, Beachfront and Gym across Islamorada rentals

4.8 Average rating
Islamorada stays are highly rated by guests – averaging 4.8 out of 5!
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