
Holiday houses in Islamorada
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Top-rated holiday rentals in Islamorada
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Florida Keys Luxury Houseboat, Dockside Paradise
Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers a unique blend of comfort, adventure, and waterfront living. Wake up to breathtaking sunrises, sip your morning coffee with all the marine life, and fall asleep to the gentle movement of the boat. Whether your celebrating something special or simply want a one of a kind getaway-it's the perfect home base for Keys adventures or peaceful retreats. An amazing experience Free park

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.

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.

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.

Oceanfront Tiny Villa in the Heart of the FL Keys
Welcome to your happy place in the beautiful Florida Keys! 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!!

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!

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!

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
Stay near Islamorada's top sights
Other great holiday rentals in Islamorada

Pristine pool front home w/ocean views Anglers 148

Islamorada bungalow 2 bed & pool

Off The Charts-Waterfront Tiki Bar & Private Dock

Paradise awaits on this cozy houseboat!

TheSandbar: Oceanfront,Pool,Free Dockage,Gameroom

Islamorada house with best location. Lic # 24-0055

OceanView Private Beach Pool Islamorada w/ Marina

Marathon Keys Escape • Pool • Hot Tub • Near Beach
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $490 AUD | $565 AUD | $577 AUD | $494 AUD | $583 AUD | $487 AUD | $500 AUD | $490 AUD | $463 AUD | $450 AUD | $460 AUD | $517 AUD |
| 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
How is the weather in Islamorada?
Islamorada has a tropical climate with warm temperatures year-round. In the summer, temperatures can reach 90°F (32°C), while winters are mild, with highs around 75°F (24°C). Rain is common from May to October, with September being the wettest month.
What are some of the best things to do in Islamorada?
Popular activities in Islamorada include snorkeling and scuba diving at the Alligator Reef, fishing in the clear blue waters, and exploring the Indian Key Historic State Park. Visitors also frequently enjoy paddle boarding, biking, and kayaking.
What is the best time of year to visit Islamorada?
The most popular time to visit Islamorada is from December to April when the weather is mild and dry. During this period, the island often hosts various events such as the Island Fest in April, which features art, food, and music.
What are the best places to stay in Islamorada?
Popular areas to stay in Islamorada include the centrally-located Islamorada Village, which has easy access to restaurants and shops. The quieter Lower Matecumbe Key is also frequently suggested for its beautiful beaches and easy access to Anne's Beach.
What are the best places to visit in Islamorada?
Popular places to visit in Islamorada include the History of Diving Museum, Anne's Beach, Theater of the Sea, and the Rain Barrel Sculpture Gallery. Visitors often explore Lignumvitae Key Botanical State Park and Indian Key Historic State Park as well.
What are some hiking trails in Islamorada?
While Islamorada is more famous for its water activities, it also has some enjoyable walking trails. The Windley Key Fossil Reef Geological State Park has several short trails that feature unique geological formations and the Indian Key Historic State Park has a walking path with interpretive signs about local history.
What are some family activities to do in Islamorada?
Families in Islamorada often enjoy exploring the Theater of the Sea, the History of Diving Museum, and the Windley Key Fossil Reef Geological State Park. A visit to the Dolphin Research Center or the Florida Keys Wild Bird Rehabilitation Center can also be a rewarding experience for children and adults alike.
What are some of the best day trip ideas in Islamorada?
Day trips from Islamorada often involve visiting the nearby Key Largo or Marathon islands, both perfect for snorkeling and wildlife watching. The vibrant city of Miami is just 1.5 hours (130 km) away and exploring the Everglades National Park is also a feasible day trip.
What types of vacation rentals are available in Islamorada?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Islamorada. From over 80 condo rentals to over 290 house rentals, we've got you covered.
Are there vacation rentals with a dedicated workspace in Islamorada?
Yes! Work meets play with ease at over 460 vacation rentals in Islamorada featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Islamorada?
Four-legged friends are welcome in Islamorada. Choose from more than 410 vacation rentals for guests traveling with pets.
Are there Islamorada vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 630 vacation homes with pools in Islamorada, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Islamorada?
Experience the best of Islamorada with our condo rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do condo rentals in Islamorada have a gym?
Absolutely! We offer over 50 condo rentals with a gym in Islamorada. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Islamorada have a bbq area?
Absolutely! We offer over 30 condo rentals with a bbq area in Islamorada. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Islamorada have self check-in?
Absolutely! We offer over 70 house rentals with self check-in in Islamorada. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Islamorada?
Islamorada has more than 580 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Islamorada?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a gym, over 110 homes with a bbq area, over 70 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
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 $60 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
800 of Islamorada holiday rentals include Wi-Fi 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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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Cocoa Plum Beach
- Coral Castle
- Calusa Beach & Loggerhead Beach
- Cannon Beach
- Far Beach
- Theater of the Sea
- Everglades Alligator Farm
- Conch Key
- Sea Oats Beach
- Monkey Jungle
- Horseshoe Beach
- Long Key State Park
- Schnebly Redland's Winery & Brewery
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Long Beach
- Bahia Honda State Park
- Sandspur Beach
- Keys' Meads




