Islamorada vacation rentals

We found 2,137 vacation rentals — enter your dates for availability

Select from 587 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 21 - Nov 28

Image gallery for Islamorada Keys Waterfront Heated Pool Hottub Luxury Canal Home w Private Dock

Waterfront Deep Water Canal
10 out of 10 rating
Exceptional
(6 reviews)

Islamorada Keys Waterfront Heated Pool Hottub Luxury Canal Home w Private Dock

Tavernier, FL

10% off
Price is CA $1,150
CA $10,460 total
includes taxes & fees
Islamorada Keys Waterfront Heated Pool Hottub Luxury Canal Home w Private Dock

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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)
  • 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)
  • Windley Key Fossil Reef Geological State Park (2.4 mi / 3.8 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?
When planning a vacation rental in Islamorada, one of the best areas to consider is the Upper Matecumbe Key. This picturesque neighbourhood offers a charming blend of natural beauty and local culture, making it an ideal spot for a relaxing getaway. Upper Matecumbe Key is renowned for its stunning waterfront views and easy access to some of the area's top attractions. One must-visit highlight is the Windley Key Fossil Reef Geological State Park, where you can explore fascinating geological features and lush landscapes. Additionally, the iconic Robbie's of Islamorada, famous for its vibrant atmosphere and opportunities to feed the tarpon, is just a short drive away.

Another excellent option is the Lower Matecumbe Key, which boasts a tranquil ambiance and an abundance of water-based activities. This area is superb for those who enjoy fishing, kayaking, or simply lounging by the water. Not far from here, you can visit the historic Indian Key State Park, an intriguing site that offers a glimpse into the area's rich history and natural beauty.
How much does it cost to rent a vacation home in Islamorada?
Prices for vacation rentals in Islamorada vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Islamorada to more spacious homes.
Are there any discounts for Islamorada vacation house rentals?
You can find great discounts on house rentals in Islamorada on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Islamorada?
For renting a beach house in Islamorada, the vibrant village is renowned for its stunning waterfront properties and relaxed atmosphere. The area around the Florida Keys, particularly near the Indian Key Historic State Park, offers a variety of vacation rentals that provide direct access to the beach, allowing guests to enjoy the picturesque views of the turquoise waters. Many properties in this region come equipped with modern amenities such as private pools, outdoor grilling areas, and spacious decks, superb for soaking up the sun or enjoying evening barbecues with family and friends.

Further along, the vicinity of Morada Bay Beach is another excellent option, featuring charming beach houses that often include direct beach access, kayaks, or paddleboards for guests to explore the surrounding waters. These rentals typically offer comprehensive kitchen facilities, air conditioning, and comfortable living areas, ensuring a homely feel during your stay. Find your rental near the beach in Islamorada.
Are there any houseboat rentals in Islamorada?
In Islamorada, houseboat rentals are indeed available, offering a unique way to experience the stunning Florida Keys. Several houseboats can be found moored in picturesque locations, providing guests with direct access to the water and breathtaking views. These rentals typically come equipped with amenities such as fully stocked kitchens, comfortable living areas, and outdoor decks for relaxing or dining al fresco. Many also feature modern conveniences like air conditioning, Wi-Fi, and sometimes even fishing gear, making them ideal for both leisure and adventure. See all houseboats in Islamorada.
What is the most popular type of vacation rental accomodation in Islamorada?
In Islamorada, vacation houses are the most popular type of rental, with approximately 552 available throughout the area. These homes are often situated near the stunning coastline and offer a variety of amenities, including spacious layouts, fully equipped kitchens, and outdoor spaces such as decks or patios for enjoying the warm Florida weather. Many of these properties also come with private pools and beach access, making them ideal for families or groups looking to unwind near the water.
Are there any family house rentals in Islamorada?
In Islamorada, there is an impressive selection of family-friendly vacation rentals, with approximately 583 options available. This charming destination, known as the "Sportfishing Capital of the World," offers homes in various neighbourhoods, including Plantation Key and Upper Matecumbe Key. Properties typically feature spacious living areas, fully equipped kitchens superb for family meals, and outdoor spaces where children can enjoy themselves.

Visitors to Plantation Key can find rentals with private pools, ideal for relaxation after a day of exploring the local beaches or indulging in water sports. Many homes also provide amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay for families. See all family-friendly rentals in Islamorada.
Can I rent a vacation home with a pool or hot tub in Islamorada?
In Islamorada, there are a significant number of vacation homes available for rent that feature pools and hot tubs, with around 616 options to choose from. This beautiful area, known as the "Sportfishing Capital of the World," offers a range of neighbourhoods, including the picturesque Plantation Key and the vibrant Upper Matecumbe Key, where these properties can be found. Find your rental in Islamorada with a pool or a hot tub.
Can I find long-stay vacation rentals in Islamorada?
A long-stay vacation rental in Islamorada is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Islamorada?
In Islamorada, there is an impressive selection of pet-friendly house rentals available, with over 350 options to choose from. This picturesque area, known for its stunning sunsets and vibrant marine life, offers a range of vacation homes that cater to both pets and their owners. Many of these rentals feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor patios where pets can enjoy the warm Floridian climate. See all pet-friendly rentals in Islamorada.
Are there any remote work vacation rentals in Islamorada?
In Islamorada, Florida, there are numerous vacation rentals suitable for remote work, with around 677 options available. This picturesque area, known for its stunning waterfront views and vibrant marine life, offers a variety of properties suiting those who need to balance work and leisure. Many of these rentals are equipped with essential remote work amenities, including high-speed Wi-Fi, dedicated office spaces, desks, and comfortable chairs, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Islamorada vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Islamorada with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Islamorada?
In Islamorada, popular rental amenities include pools, with many properties offering shared or heated options to enhance the experience. Travellers can expect rentals equipped with free in-room Wi-Fi, great for staying connected while enjoying the beautiful surroundings. Additionally, most accommodations come with fully equipped kitchens, allowing guests to prepare their own meals and enjoy the flexibility of dining in.
When is the best time to visit Islamorada for a vacation rental?
The best time to visit Islamorada for a vacation rental is during the peak season, which runs from February to April. This period is particularly popular as travellers flock to the area to enjoy its stunning beaches and world-class fishing opportunities. With temperatures typically ranging from the mid to high 20s Celsius, the weather is great for outdoor activities such as snorkelling, diving, and exploring the vibrant marine life in the clear waters.

March stands out as the most popular month to visit, drawing in a lively crowd eager to soak up the sun and partake in the many water sports available. The warm climate and the festive atmosphere create an ideal setting for relaxation and adventure alike.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience, allowing you to enjoy the natural beauty of Islamorada with fewer crowds. Plus, with pleasant temperatures in the mid-20s Celsius, it's still a lovely time to explore the local attractions, such as the renowned history of the area or the tranquil beaches.
How early should I book a Islamorada vacation rental?
Book your Islamorada vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Islamorada home rental booking on Vrbo?
To find Islamorada vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Islamorada vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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