Islamorada vacation rentals

We found 2,124 vacation rentals — enter your dates for availability

Select from 590 houses, 76 apartments, and other vacation rentals to find the perfect place for your stay in Islamorada. Vacation homes offer the amenities you expect for your stay with friends, family, or just your pet, including parking and a garden. At the end of the day, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Islamorada

Showing deals for:Nov 7 - Nov 14
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Find out more about Islamorada

Find out more about Islamorada

Why visit Islamorada

  1. Stunning Beaches: Islamorada boasts beautiful sandy beaches perfect for relaxation and family fun.
  2. Outdoor Adventures: Engage in activities like fishing, snorkeling, and kayaking in the crystal-clear waters.
  3. Vibrant Local Culture: Experience the friendly atmosphere and unique charm of the local community.
  4. National Parks: Explore nearby national parks that showcase the region's incredible flora and fauna.
  5. Diverse Accommodations: Choose from a variety of vacation rentals and resorts that suit all budgets.

Popular types of accommodation in Islamorada

Planning a getaway to Islamorada? You're in for a treat! Discover a variety of vacation rentals, including houses, condos, and villas that cater to every taste and budget. Whether you're seeking the charm of the Florida Keys or the comforts of the Islander Resort, Islamorada offers the perfect backdrop for your next adventure. Enjoy transparency, savings, and reassurance as you explore the best Islamorada vacation rentals available!

  • Houses: The top choice for visitors in Islamorada, these homes offer spacious and comfortable living, perfect for families or groups seeking a home-away-from-home experience.
  • Condos: A popular option for couples and small families, condos provide modern amenities and often stunning views of the ocean.
  • Villas: Ideal for those desiring luxury, villas in Islamorada offer upscale accommodations and private spaces.
  • Apartments: A convenient choice for solo travellers or couples, apartments provide a cozy base for exploring the area.
  • Caravan Parks: Offering a unique outdoor experience, caravan parks are perfect for those wanting to connect with nature while enjoying a range of facilities.**

Top attractions in Islamorada

Islamorada is a fantastic destination for families seeking outdoor and beach vacations. With its stunning marinas, beautiful beaches, and nearby national parks, visitors can enjoy a variety of activities that blend culture and nature. Exploring Islamorada offers a wealth of experiences for those looking to relax or seek adventure in this picturesque location.

  1. Anne's Beach: This serene beach offers a perfect escape with its soft sands and calm waters, ideal for basking in the sun or a leisurely stroll. The laid-back atmosphere makes it a popular spot for relaxation and enjoying the natural beauty of Islamorada.
  2. Bud n' Mary's Dive Center: A premier marina for adventure enthusiasts, this dive center provides access to exhilarating water sports, including scuba diving and fishing. Experience the thrill of exploring vibrant marine life in the stunning Florida Keys.
  3. Windley Key Fossil Reef Geological State Park: This unique park features fascinating geological formations and scenic trails. Visitors can hike through lush landscapes while learning about the area's ancient fossilized reefs and diverse ecosystems.

Things to do recommended for couples

Ready for a romantic getaway in Islamorada? Dive into adventure at Florida Keys Dive Center, just 12.9km away, or explore the charming shops at Rain Barrel Village. Enjoy the vibrant local culture and create unforgettable memories together in this beautiful slice of paradise.

Things to do recommended for families

Experience family fun at Jacob's Aquatic Center, located 27.4km from Islamorada. With its welcoming atmosphere, families can splash around in the pools and enjoy various water activities, making it a perfect spot for kids and parents alike.

Things to do recommended for groups

In Islamorada, your group can enjoy the lively atmosphere at Florida Keys Brewing Co. and Islamorada Brewery & Distillery, both offering unique local brews. For a bit of a drive, visit Jimmy Johnson's Big Chill for delightful drinks and entertainment vibes, enhancing your vacation experience.

What do I need to keep in mind when booking a vacation in Islamorada

If you're planning a trip with friends, family, or pets, or if you're interested in extended stays, it's important to prioritize your preferences when searching. Here are some helpful booking tips for Vrbo.

  • Traveling to Islamorada with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Islamorada with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Islamorada: For many families, a trip isn’t truly complete without their furry companions. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Islamorada: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider additional features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Islamorada

Islamorada, Florida, offers a perfect blend of relaxation and adventure for Canadian travellers. With its stunning beach resorts and breathtaking ocean views, this island paradise invites families and outdoor enthusiasts alike to unwind in its tranquil atmosphere. Explore the heart of Islamorada, where friendly locals and vibrant adventures await. Whether you're lounging on the beautiful beaches or embarking on exciting excursions, your vacation in this enchanting destination promises unforgettable memories.

  • Venetian Shores: Nestled in the vibrant area of Islamorada, Venetian Shores is a charming neighbourhood that draws visitors seeking a blend of outdoor adventures and family-friendly experiences. With its proximity to beautiful beaches and lush landscapes, it’s an ideal spot for leisure activities. The local shopping area and mall centre offer a variety of retail options, making it easy to find unique souvenirs or enjoy a delightful meal. Don’t miss the opportunity to explore nearby landmarks like family beaches and scenic islands that showcase the natural beauty of the Florida Keys.
  • Lower Matecumbe Beach: Located near the heart of Islamorada, Lower Matecumbe Beach is a picturesque neighbourhood perfect for families and beach enthusiasts. This area features stunning coastlines and inviting recreational spaces, ideal for sunbathing or beach volleyball. The local shopping area and mall centre provide convenient access to dining and shopping options, making it a great stop for family outings. The nearby beaches and scenic islands offer opportunities for water sports, relaxing walks, and picturesque sunsets, enhancing your vacation experience in the Florida Keys.
  • Lower Matecumbe Key: As a natural island gem, Lower Matecumbe Key is a tranquil destination that enchants visitors with its serene beaches and lush surroundings. This area is perfect for families seeking outdoor adventures and relaxation. You'll find shopping mall centres and recreational areas that cater to all ages. The local attractions, including pristine beaches and stunning islands, provide a wonderful backdrop for activities such as swimming, fishing, and exploring the local marine life. Lower Matecumbe Key is a delightful escape into the beauty of the Florida Keys.

Best time to go to Islamorada

If you're planning a trip to Islamorada, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January70.0°F (21.1°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
February71.8°F (22.1°C)No Rain (Dry)Mostly SunnyAverageAverage
March72.9°F (22.7°C)No Rain (Dry)Mostly SunnyModerately HighAverage
April76.6°F (24.8°C)No Rain (Dry)Mostly SunnyModerately HighAverage
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly High
July83.8°F (28.8°C)Light RainMostly SunnyModerately HighSlightly High
August84.4°F (29.1°C)Light RainMostly SunnyAverageAverage
September83.3°F (28.5°C)Light RainMostly SunnyAverageSlightly Low
October80.2°F (26.8°C)Light RainMostly SunnyModerately LowSlightly Low
November75.9°F (24.4°C)Light RainMostly SunnyModerately LowAverage
December72.9°F (22.7°C)No Rain (Dry)Mostly SunnyModerately LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, continue from where you last left off, or easily view and organize your travel plans. Your saved or booked properties will be neatly arranged under categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Travel to tranquil Islamorada

Enjoy the area's entertainment, opera and theater scene and make a vacation rental your home during your stay in Islamorada. This relaxing city is known for its fishing, seaside and diving. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Islamorada

Are you hoping to find attractions to visit during your stay? Travelers enjoy fun activities like fishing and diving. Venture out of your cozy vacation rental and experience everything that makes Islamorada a one-of-a-kind vacation spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • MarineLab Undersea Laboratory (20.3 mi / 32.7 km)
  • Jacob's Aquatic Center (16.6 mi / 26.7 km)

Exploring the natural landscape of Islamorada

Travelers appreciate the beautiful ocean views and breathtaking sunsets, which is just a taste of what Islamorada has to offer. Whether you're an active traveler or just want to take in the scenery, Islamorada is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Islamorada County Park (4.5 mi / 7.2 km)
  • Founders Park (4.6 mi / 7.4 km)
  • Anne's Beach (8.8 mi / 14.1 km)
  • Fiesta Key (11.8 mi / 19 km)
  • Curry Hammock State Park (25.6 mi / 41.3 km)
  • Coco Plum Beach (26.9 mi / 43.4 km)

Transportation to and around Islamorada

The nearest airport is in Marathon, FL (MTH-Florida Keys Marathon), located 30 mi (48.2 km) from the city center.

Frequently asked questions

What is the best area to stay in Islamorada when booking a vacation rental?
If you're planning a break in Islamorada, Venetian Shores is one of the most sought-after destinations to stay. No matter your style of travel, Vrbo is sure to have a vacation rental here that's just right for you.
What is the most popular type of vacation rental accommodation in Islamorada?
Houses are the most popular style of vacation rental in Islamorada, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in loads of sizes and shapes. Filter our options to find your perfect fit.
How much does it cost to rent a vacation rental in Islamorada?
Season, property type and length of stay are some things that can influence the price of a vacation home. Simply add your dates of travel to find your ideal escape. From homey country cottages to expansive villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in Islamorada?
When you travel and the style and size of the property will influence the cost of your beachside stay. Enter your Islamorada travel dates to see your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to choose the features and amenities you need.
Are there pet-friendly vacation rentals in Islamorada?
Pack a travel bag and a bone for the pup in your life because Islamorada has 166 stays that throw out the welcome mat to doggie guests. Let your furriest pal enjoy fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Islamorada?
Mark the "pool" box in our filter tool and you can choose from 122 houses with private pools in Islamorada on Vrbo. Morning dip, sunset soak or midnight swim? How you spend your free time is up to you when your vacation property has its own swimming pool.
What are popular rental amenities in Islamorada?
Some of the most popular rental amenities people look for in Islamorada are a barbecue grill, a chef and a sauna. Whether you're on a trip with family, pals or even pets, Vrbo vacation rentals have the best amenities for chilling out with the people you cherish the most.
Are there large group vacation rentals in Islamorada?
You can pick from 18 vacation properties in Islamorada that can host a group of 10 or more guests. Whether you're organizing time away with the family or an event like an anniversary, there's plenty of space to get your loved ones together under the same roof.
Are there vacation rentals in Islamorada that welcome kids?
With 166 family-friendly vacation rentals to select from in Islamorada, now is a great time to introduce the kiddos to the joys of travel. Simply click on our "Properties good for families" filter to locate stays that feature conveniences perfect for traveling families, like dining rooms, pools, entertainment units and bunk beds.
What are the top attractions for families in Islamorada?
There's a ton of amazing things to do and see with the family in Islamorada, such as:

  • Theater of the Sea
  • Annes Beach
  • Robbies

Are there one-bedroom vacation rentals in Islamorada?
Islamorada has 16 one-bedroom rentals on offer. Often positioned in popular areas due to their smaller size, a one-bedroom vacation rental is perfect if you're getting away with your partner or a buddy. And with plenty of home comforts like full kitchens and more privacy than a standard hotel, you'll be able to kick back while discovering this exciting destination.
Can I find two-bedroom vacation rentals in Islamorada?
Take your pick of 57 two-bedroom properties in Islamorada. Settle the kids into the second room or maybe fill it with a couple of your besties. There's space for whoever's lucky enough to be coming along for the ride.
Are there vacation rentals with WiFi in Islamorada?
Whether you want to keep up with world events, check emails or surf your social networks, there are 77 vacation homes with WiFi in Islamorada. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Islamorada?
Pick your dates and then make use of our filters to find vacation rentals with air conditioning in Islamorada on Vrbo. With 165 air-conditioned properties available, you can look forward to a cool and comfy break.
How old do you have to be to rent a vacation rental in Islamorada?
It's a good idea to check with the Islamorada vacation property you're considering on Vrbo as the minimum age varies. However, normally it's 16, 18 or 21.
How long can I rent a vacation rental in Islamorada for?
The amount of time you can stay in an Islamorada vacation rental for differs depending on the property. Just put in your dates of travel to browse available options offering longer term stays. They have all the things you need to make your extended trip more convenient and comfortable, such as laundries and air conditioning. Some Vrbo vacation properties may also offer discounted weekly or monthly prices, so you can hang around longer for less.

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