Islamorada vacation rentals

We found 2,115 vacation rentals — enter your dates for availability

Select from 594 houses, 84 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:Sep 5 - Sep 12
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Find out more about Islamorada

Find out more about Islamorada

Why visit Islamorada

  1. Beautiful Beaches: Enjoy pristine sandy shores perfect for sunbathing and swimming.
  2. Outdoor Adventures: Dive into vibrant coral reefs or explore state parks for hiking and wildlife watching.
  3. Fresh Seafood: Savor delicious local cuisine at charming eateries offering fresh catches.
  4. Family-Friendly Atmosphere: Experience a welcoming environment ideal for families and outdoor enthusiasts alike.
  5. Variety of Accommodations: Choose from vacation homes, condos, or luxurious villas to suit every traveler's needs.

Popular types of accommodation in Islamorada

Discover the perfect getaway with Islamorada vacation rentals, featuring a variety of accommodations to suit every traveler. Whether you prefer a private vacation home, a cozy condo, or a luxurious villa, you'll find the ideal setting for your trip. With our transparent options and great savings, exploring the beautiful Florida Keys has never been easier. Choose from the best Islamorada rentals and create unforgettable memories in this tropical paradise!

  • Houses: These spacious homes are the top choice for vacationers in Islamorada, ideal for families or groups seeking comfort and privacy.
  • Condos: A popular option for those wanting a blend of home-like amenities and resort-style living, condos offer stunning views and convenient access to local attractions.
  • Villas: Luxurious and often featuring private pools, villas provide an upscale vacation experience for those looking to indulge.
  • Apartments: These cozy rentals are perfect for couples or solo travelers, offering a homey feel with the convenience of a full kitchen.
  • Caravan Parks: For an adventurous stay, caravan parks offer camping facilities and easy access to the beautiful outdoors of Islamorada.**

Top attractions in Islamorada

Islamorada, Florida, is the perfect destination for families and outdoor enthusiasts seeking a beach vacation. Here, you can explore a variety of attractions, including marinas, beautiful beaches, and nearby state parks. Whether you're looking for cultural experiences or simply want to relax by the ocean, Islamorada has something for everyone to enjoy, making it an ideal spot for both adventure and relaxation.

  1. Anne's Beach: This beautiful beach offers a laid-back atmosphere perfect for sunbathing and relaxing. With its shallow waters and picturesque scenery, it's ideal for families and those seeking a tranquil beach experience.
  2. Bud n' Mary's Dive Center: A must-visit for adventure enthusiasts, this marina provides access to thrilling water sports, fishing charters, and diving excursions. Experience the vibrant underwater world while enjoying the lively outdoor vibes.
  3. Windley Key Fossil Reef Geological State Park: Explore stunning natural landscapes and fascinating fossilized coral reefs. This park is perfect for hiking and wildlife observation, offering a unique blend of adventure and scenic beauty.

Things to do recommended for couples

For a romantic getaway in Islamorada, dive into adventure at the Florida Keys Dive Center for an unforgettable underwater experience. Then, explore the charming shops at Rain Barrel Village, perfect for picking up unique souvenirs and enjoying the local vibe together.

Things to do recommended for families

Families will have a blast at Jacob's Aquatic Center, an aquatic center located 17 miles from Islamorada, offering fun water activities and family-friendly vibes. It's a perfect spot for kids to splash around and enjoy a day of excitement together.

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

When planning your trip, whether you’re traveling with friends, family, pets, or looking for an extended stay, be sure to use the appropriate filters to match your needs. 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 features like a complete kitchen or outdoor area for group gatherings. Luckily, you can search for all these options and more on Vrbo.
  • Traveling to Islamorada with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with 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 vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Islamorada: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Islamorada

Islamorada, Florida, is a dream getaway known for its idyllic island vibe and family-friendly atmosphere. Explore beautiful beaches, indulge in outdoor adventures, and bask in the relaxation that this charming destination offers. Whether you're diving into vibrant coral reefs or enjoying fresh seafood at local eateries, the Islamorada area promises a memorable vacation spot. With friendly people and a welcoming environment, your experience in this tropical paradise will be nothing short of unforgettable.

  • Venetian Shores: Nestled in the scenic area of Islamorada, Venetian Shores is a charming neighborhood that offers a delightful blend of outdoor adventures and family-friendly experiences. This picturesque locale is known for its stunning beaches and recreational areas, making it an ideal spot for those looking to relax by the water or partake in various outdoor activities. Visitors can explore the local shopping area and mall centers, perfect for picking up unique souvenirs or enjoying a meal with family. With its close proximity to beautiful islands and family beaches, Venetian Shores provides an enchanting backdrop for a memorable vacation.
  • Lower Matecumbe Key: As an idyllic island destination near Islamorada, Lower Matecumbe Key boasts breathtaking natural beauty and a laid-back atmosphere. Perfect for beachgoers and outdoor enthusiasts, this area features pristine beaches and a variety of recreational activities to enjoy. Visitors can unwind at luxurious resorts or explore local shopping mall centers for a taste of island life. The inviting family beaches and serene atmosphere make Lower Matecumbe Key a wonderful escape for families seeking both relaxation and adventure in the Florida Keys.
  • Lower Matecumbe Beach: Located in the heart of Islamorada, Lower Matecumbe Beach is a welcoming neighborhood that captures the essence of a quintessential beach vacation. With ample opportunities for outdoor activities and family fun, this area is perfect for sun-seekers and adventure lovers alike. Visitors can delight in recreational areas, local shopping centers, and the beautiful beach that defines this coastal gem. With its proximity to stunning islands and family-oriented attractions, Lower Matecumbe Beach offers a perfect blend of relaxation and excitement for all ages.

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 a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, opting for a longer stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo and enjoy the benefit of earning OneKeyCash™ on your entire reservation. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on qualifying bookings. Sign up today and begin your journey to savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers an easy-to-use platform for planning your trips. You can start new itineraries, resume planning from where you last stopped, or review and organize all your travel plans in one place. Your saved or booked properties will be neatly organized into categories such as Potential, Upcoming, and Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-us/trips.

**Based on Vrbo properties bookings.

Enjoy island paradise vacation homes on Islamorada

Encompassing 6 of the Florida Keys, Islamorada is a paradise for beachgoers. In addition to its pristine beaches and turquoise waters, Islamorada has an abundance of activities in, under, and above the water for any inclination. Whatever you’re looking for from your beach getaway, vacation home rentals get you right in the center of all Islamorada has to offer.

Top island adventures near vacation rentals in Islamorada

Islamorada is a popular destination with a little bit of everything, ranging from watersports and beach activities to historic sites and nature trips. Vacation homes can be found near must-visit places like the Theater of the Sea, a marine park with interactive dolphin and sea lion shows, and Windley Key Fossil Reef Geological Park, a historic limestone quarry with fossilized coral and hiking trails. The History of Diving Museum is great for history and nature lovers, due to its collection of artifacts and exhibits celebrating the evolution of diving. Families will enjoy Founders Park, a 40-acre space with a beach, a pool, sports facilities, a playground, and other recreational spaces. The Rain Barrel Sculpture Gallery, a rustic spot with local sculpture, paintings, pottery, and other works, is a lovely attraction for art lovers.

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:

  • Anne's Beach (8.8 mi / 14.1 km)
  • Baker's Cay Resort Beach (13.9 mi / 22.4 km)
  • Long Key State Park (14.4 mi / 23.1 km)
  • John Pennekamp Coral Reef State Park (19.8 mi / 31.8 km)
  • Coco Plum Beach (26.9 mi / 43.4 km)
  • Windley Key Fossil Reef Geological State Park (2.4 mi / 3.8 km)

Beachside nirvana in Islamorada

Islamorada offers an idyllic seaside escape with its many pristine beaches. Vacation rentals are available near some of the best shorelines, such as Anne’s Beach, a pet-friendly, family-friendly area with soft sand, a boardwalk, and seaside essentials, and Holiday Isle Beach, a quiet fishing coastline with colorful marine life, gentle surf, and warm waters. Islamorada Library Beach offers a secluded retreat with stunning views of the water and a nearby park for small children. Long Key State Park, a quiet beach with clear water that’s popular for diving and snorkeling, also has beautiful hiking trails nearby so you can take in the landscape.

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.

Transportation in Islamorada

Islamorada is accessible from mainland Florida by a highway bridge, but once there, you’ll have limitless transportation options to get you to and from the vacation rentals. Shuttle and airport transportation are available, as well as car rentals and taxis, to get you through the area and to nearby destinations. Bikes and motorbikes are available to rent, giving you an opportunity to explore Islamorada on your own schedule, and many destinations are close enough to walk.

Sample Islamorada’s regional cuisine

From authentic Tuscan cuisine to Caribbean favorites, Islamorada offers a range of exciting culinary options to suit every palate. Whether you prefer fresh-caught seafood in a restaurant with ocean views, or you want to settle into a casual restaurant with the kids near your summer rental, the diverse eateries in Islamorada ensure you’ll find just what you need to satisfy your cravings.

Frequently asked questions

What is the best area to stay in Islamorada when booking a vacation rental?
If you’re planning to explore Islamorada, Venetian Shores is among the most sought-after destinations to stay. Whatever your style of travel, Vrbo is bound to have a vacation home here that has exactly what you need.
What is the most popular type of vacation rental accommodation in Islamorada?
Condos are the most popular kind of vacation rental in Islamorada, according to our data. Even if you’ve got something bigger or smaller in mind, Vrbo has vacation homes in a variety of shapes and sizes. Look over our options to find your perfect match.
How much does it cost to rent a vacation rental in Islamorada?
Length of stay, season and property type are some factors that can determine the price of a vacation home. Simply enter your dates of travel to find your perfect match. From comfy cottages to sprawling luxury villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Islamorada?
The average price for a vacation rental close to the beach in Islamorada depends on when you’re going and the style and size of property you’re searching for. Find prices easily on Vrbo by entering the dates you’ll be traveling. Then use the filter tool to pick the number of bedrooms and amenities important to you, like a pool, air conditioning and WiFi.
Are there pet-friendly vacation rentals in Islamorada?
Pack a travel bag and a bone for the pup in your life because Islamorada has 387 vacation rentals that throw out the welcome mat to doggie guests. Let your happy hound join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check the “Pets allowed” filter box.
Can I rent a house with a pool in Islamorada?
Tick the “pool” box in our filter tool and you can choose from 283 houses with private pools in Islamorada on Vrbo. Gentle soak, ball games or noodle joust? How you spend your free time is up to you when your vacation property comes with its own pool.
Are there vacation rentals in Islamorada that welcome kids?
Bring the entire group together for an epic adventure in Islamorada at one of our 382 family-friendly vacation rentals. A lot of these stays provide amenities that are great for getaways with the little ones, like laundries, bunk beds and entertainment areas. Simply click on the “Properties good for families” filter and choose your favorite option.
What are the top attractions for families in Islamorada?
Keeping the kiddos entertained during your stay in Islamorada is a breeze with these exciting family-friendly attractions:

  • Windley Key Fossil Reef Geological State Park
  • Bud n’ Mary’s Dive Center
  • Theater of the Sea

Are there vacation rentals with WiFi in Islamorada?
You can pick from 173 vacation rentals with WiFi in Islamorada. If you want to disconnect from the world during your break, but still need to be connected to the internet, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Islamorada?
Choose from 383 Vrbo vacation homes with air conditioning in Islamorada giving you that gentle, cool breeze and extra bit of comfort. Simply enter your preferred dates of travel and then take advantage of our filters to search for properties with air conditioning.
How old do you have to be to rent a vacation rental in Islamorada?
The minimum age allowed can differ between properties on Vrbo, so check the rules of the vacation home in Islamorada you’re considering. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Islamorada for?
It really depends on the Islamorada property. To see all available options offering extended stays, just enter your travel dates and guest number into Vrbo’s search page. Enjoy having the property to yourself, along with home comforts like a fully-equipped kitchen, air conditioning and a yard where the kids can run around and play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Islamorada?
On Vrbo, we’ve got plenty of fabulous deals and discounts for Islamorada. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re planning a mini vacay or a much longer stay, Vrbo offers lots of options for every style and budget.

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