Islamorada was where back country sport fishing and salt water fly fishing first burst onto the scene. The 'fishing capital of the world' also has the world's highest density of professional offshore charter boats. Islamorada, which means "purple isles," is also a popular wedding destination, thanks to its raw beauty and crystal blue waters. There's much happening here, from exciting fishing activities to art walks and romantic seaside cafés. Book your Islamorada vacation rental to see what's in store.
Choose the perfect vacation rental
Best Vacation Home Deals in Islamorada
Save up to 45%
Discover a vacation home meeting your expectations among the 1,808 welcoming options from 10 providers in Islamorada. Using HomeToGo you can instantly search and compare the prices of each available property to discover the best deal and save up to 49%.
Top-Rated Rentals and Accommodations in Islamorada
Book Vacation Rental Offers with the Highest User Rating
Recommended Vacation Rentals in Islamorada
Find your perfect vacation rental in Islamorada: from $157 per night
Budget-friendly Vacation Rentals in Islamorada
Find Fantastic yet Inexpensive Offers
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Islamorada and book a vacation rental with air conditioning.
Apartments With Balconies or Patios
Looking for a home with a balcony? Check out these vacation homes in Islamorada with their own private patios and balconies.
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Islamorada accommodation with high-speed internet.
Popular Rental Amenities in Islamorada
Check above for the most selected filters in Islamorada and the number of vacation rentals that offer them. Many properties in Islamorada offer "Pool" or "Pets allowed," which makes it a wonderful vacation destination if you want a rental with a pool or you bring your pet everywhere. You could even look for rentals if you want a rental with a fireplace (250 rentals include "Fireplace" in Islamorada) or if you want a rental providing a crib (111 rentals in Islamorada include "Crib").
Waterfront Vacation Rentals in Islamorada
Want to find the perfect beach house rental in Islamorada?
Price and Availability Index in Islamorada
The Weather in Islamorada
Find the Islamorada climate diagram. On average, the warmest month is July. On the contrary, the coolest month is February. The rainiest month is September while the driest month is February.
7-Day Weather Forecast in Islamorada
Accommodations for your vacation in Islamorada
Cuisine of Islamorada
Seafood enthusiasts won't be disappointed with Islamorada's culinary offerings. Choose from fresh-off-the-nets seafood served in all kinds of settings — tiki-covered huts, marina-facing fish houses, beachfront cafés or romantic, secluded bistros. The waterfront is dotted with restaurants, serving everything from Mediterranean cuisine, sushi, organic salads, sandwiches and meatball subs.
Enjoy dinner and live entertainment at the waterfront cafés that serve excellent seafood: there's fried oysters, peel-and-eat-shrimp, and fish sandwiches galore. For the "freshest sushi in all the Keys!" and a hefty beer, wine and sake list, Kaiyo Grill & Sushi does the trick. Don't forget to pack some takeaway to feast on when you return to your Islamorada vacation rental.
The weather in Islamorada
The best time to visit is between December and May, when outdoor activities can be enjoyed under sunny, blue skies. Your vacation home in Islamorada should be booked in advance during this peak season. For those who prefer some peace and quiet, as well as discounted prices on rentals, October and November is a great time to visit.
The must-see sights of Islamorada
Most people come to Islamorada for its scenery and sunsets. The sea facing restaurants are perfectly aligned to allow diners gorgeous views of the sun sinking into the ocean. From the Islamorada Fist Company restaurant, you can watch sharks being fed while you enjoy your evening meal, as the event usually takes place around sunset. It's also quite possible to enjoy the sunset from the privacy of your sea-facing vacation rental on Islamorada.
Enjoy tropical evenings with relaxed music at the waterfront ICE Amphitheater, housed inside Islamorada Founders Park. This pet-friendly park also features an Olympic-sized pool, ball fields, a shallow water beach, water sports rentals and a skate park. Casa Mar Village meanwhile, is recommended for its local fish market, waterfront shopping and outdoor adventure sports activities. The kids will enjoy hand-feeding giant silver tarpons at Robbie's Marina. Then take them to a fun dolphin, sea lion and parrot show at Theater of the Sea marine mammal park.
Art and culture on Islamorada
The Coral Shores Performing Arts Center delights audiences with its top-notch productions. Meanwhile the monthly Third Thursday Art Walk organized by the Morada Way Arts & Cultural District is a great way to get acquainted with the town's art spaces and boutiques. The event brings together artisans, sculptors, jewelers, photographers and travelers who enjoy the artist receptions, music, sunsets and other fun activities.
The Jannette De Llanos Art Gallery showcases oil paintings and graphic art of the Florida Keys & beyond, while the Pasta Pantaleo Signature Gallery houses Pasta's sportfish paintings that are vivid and rich in their color schemes. For a look at the artworks of local photographers, painters, sculptors, and mixed media artists, visit Gallery at Ocean Sotheby's International Realty. Lastly, there's Crane Point Museum & Nature Center which regales visitors with its interpretative displays of marine life, local wildlife and exhibits.
Excursions and day trips beyond Islamorada
Islamorada boasts rare and extraordinary brimming patch reefs, which is good news for divers. An hour south from your vacation home on Islamorada, lies the Bahia Honda State Park where oceanside camping is possible. Enjoy kayaking, fishing, biking, and snorkeling among other great activities. Take time off to explore Islamorada's colorful shallow coral reefs, its shipwrecks, and an interesting underwater hub for scientific research, called the Aquarius.
Pickles Reef is perfect to spot flamingo tongue cowries and banded coral shrimps. Bud n' Mary's is another popular marina known for its sportfishing shows, chartered fishing expeditions, pontoon boats, and deli's serving excellent coffee by the sea. End the day by retiring back at your sea facing Islamorada vacation rental.
Legendary authors such as Ernest Hemingway have been inspired right here in Islamorada! Come over with the family and book your vacation rental on Islamorada today. The isles are waiting.
Lobster Trap Art Gallery
The vivid artworks at this exciting gallery will ensnare your gaze just like the lobsters in the traps outside its doors.
The Rain Barrel Artisan Village
The perfect day out involves exploring this picturesque artists' village, where there are any number of craft workshops to get involved in, plus exquisite art to discover and take home. Jewellery, sculpture and fine art are just the start.
Florida Keys Brewing Company
This family run microbrewery is a delight, and is ideally situated in the arts and cultural district of town. Enjoy tours, talks and of course, tastings.
History of Diving Museum
A trip to Florida isn't complete without exploring the ocean. Learn about the technical and historical aspects of this pastime through oral exhibits and artefacts found beneath the waves.
Theater of the Sea
Live the dream and swim with Flipper at this incredible center, dedicated to marine life. Seals, dolphins and parrots perform in mesmerising sealife shows.
Information about vacation rentals in Islamorada
|🏡 Vacation rentals available||1,808 homes|
|💳 Possible discounts||up to 49%|
|🌙 Nightly prices starting at||$157|
|⭐ Popular amenities||Pool, Pets allowed and Fishing|
|🐾 Pet friendly homes||414 homes|
|🏊 Vacation rentals with pools||1,509 homes|
Frequently Asked Questions
What is the nightly price for a vacation home in Islamorada?
The average accommodation in Islamorada is priced at $157 per night. If you’re interested in a house rental, the average price is $812 per night. A apartment rental Islamorada will cost $470 per night on average.
How many vacation homes are available for booking in Islamorada?
There are 1,808 rentals to choose from for your next trip.
What amenities are most popular for vacation homes in Islamorada?
If you're looking to book a vacation rental in Islamorada, others search for homes with Pool, Pets allowed and Fishing.
How many vacation homes with pools are there in Islamorada?
There are 1,509 vacation homes across 10 providers in Islamorada.
Are dogs allowed in vacation homes in Islamorada?
Absolutely, there are 414 rentals in Islamorada that allow dogs and the average nightly rate is $871.
When is it better to travel to Islamorada?
July and August are the warmest months in Islamorada with temperatures around 91 °F. The coldest months in Islamorada are February and January, with 68 °F on average.
Top cities to visit
- Vacation Rentals in Branson, MO
- Vacation Rentals in Blue Ridge, GA
- Dallas Condos & Vacation Rentals
- Vacation Rentals in Austin
- Condos & House Rentals in Orange Beach
- Vacation Rentals in Palm Springs
- Condos & House Rentals in Tampa
- House Rentals & Condos in Phoenix
- Vacation Rentals in Siesta Key
- Vacation Rentals in Hershey
- Vacation Rentals in Saint Augustine
- House Rentals & Condos in Philadelphia
- Condo & House Rentals in Albuquerque
- Vacation Rentals in Breckenridge
Vacation Destinations Near Islamorada
Tavernier Vacation Rentals
Long Key Vacation Rentals
Vacation Rentals in Key Largo
Duck Key Vacation Rentals
House Rentals in Marathon
Key Colony Beach Vacation Rentals
Homestead Vacation Rentals
Big Pine Key Vacation Rentals
Kendall Vacation Rentals
Cudjoe Key Vacation Rentals
Condos in Coral Gables
South Miami Vacation Rentals
Key Biscayne Vacation Rentals
Doral Vacation Rentals
Houses & Vacation Rentals in Miami
Fisher Island Vacation Rentals
Palm Island Vacation Rentals
House & Vacation Rentals in Miami Beach
Surfside Vacation Rentals
North Miami Vacation Rentals
Miramar Vacation Rentals
House & Vacation Rentals in Key West
Sunny Isles Beach Vacation Rentals
Aventura Vacation Rentals
House Rentals in Pembroke Pines
Hallandale Beach Vacation Rentals
Condos in Hollywood
Lodging & Cabins in Sunrise
Houses & Vacation Rentals in Fort Lauderdale
Tamarac Vacation Rentals
Lauderdale-by-the-Sea Vacation Rentals
Coral Springs Vacation Rentals
Condos in Marco Island
Condos in Pompano Beach
Lighthouse Point Vacation Rentals
Deerfield Beach Vacation Rentals
Condos in Boca Raton
Highland Beach Vacation Rentals
Condo & House Rentals in Naples
Condos in Delray Beach
House Rentals in Boynton Beach
North Naples Vacation Rentals
Vanderbilt Beach Vacation Rentals
Vacation Rentals in Bonita Springs
Lake Worth Vacation Rentals
Estero Vacation Rentals
Palm Beach Vacation Rentals
Condos in West Palm Beach
Condos in Fort Myers Beach
Lehigh Acres Vacation Rentals
Top Vacation Ideas
- Romantic Getaways in Ohio
- Christmas Markets in Vancouver
- Romantic Getaways in Pennsylvania
- Romantic Getaways in Florida
- Bali Honeymoon
- Romantic Getaways in Colorado
- South Padre Island Spring Break Hotels & Vacation Rentals
- Christmas Markets in New York
- Costa Rica Honeymoon
- Romantic Getaways in Virginia
- Lake Havasu Spring Break Hotels & Vacation Rentals
Explore More Vacation Ideas
Family Vacations in Kentucky
Airbnbs in Lake Placid
Airbnbs in Downtown Miami
Spa Getaways in Arizona
Gatlinburg Hotels & Vacation Rentals for Thanksgiving
Cabin rentals in Idaho
Spring Break in San Antonio
Williamsburg Hotels & Vacation Rentals for Thanksgiving
Airbnbs in Kiawah Island
Nashville Hotels & Vacation Rentals for New Year's Eve
Airbnbs in Aurora
Airbnbs in South Dakota
Skiing in Taos Ski Valley
Pet Friendly Rentals in Sandestin
Summer Vacations in New York City
Top Destinations for a Weekend Getaway in Pennsylvania
Honeymoon in Orlando
Airbnbs in James Island
City Breaks in Gatlinburg
Summer Vacations in Colorado
Charleston Hotels & Vacation Rentals for Christmas