Islamorada holiday lettings

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

Select from 590 houses, 76 apartments and other holiday rentals to find the perfect place for your stay in Islamorada. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as a pool and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Islamorada

Showing deals for:7 Nov - 14 Nov
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Why visit Islamorada

  • Stunning beaches: Relax on beautiful sandy shores, perfect for sunbathing, swimming, and water sports.
  • Outdoor adventures: Enjoy kayaking and snorkelling in crystal-clear waters, surrounded by vibrant marine life.
  • Cultural experiences: Immerse yourself in the local culture with charming eateries and friendly atmospheres.
  • National parks: Explore the nearby national parks, offering lush landscapes and diverse wildlife.
  • Variety of accommodation: Choose from a range of holiday rentals, from private villas to cosy condos, tailored to your needs.

Popular types of accommodation in Islamorada

Explore a variety of holiday rentals in Islamorada, from houses and villas to cosy condos. Whether you're travelling with family, friends, or on a romantic getaway, there's an ideal accommodation to suit your needs. With transparency and savings at the forefront, our platform ensures you can find the perfect vacation rental for your stay in this stunning destination.

  • Houses: The top choice for visitors in Islamorada, these homes offer a spacious and comfortable environment for families or groups seeking a getaway.
  • Condos: A popular option, these self-contained units provide a blend of convenience and luxury, perfect for couples or small families.
  • Villas: These elegant properties offer a touch of luxury, ideal for those wanting an upscale holiday experience.
  • Apartments: A practical choice for solo travellers or couples, providing all the essentials for a pleasant stay.
  • Caravan Parks: A charming option for those who enjoy a more rustic experience while still being close to nature.**

Top attractions in Islamorada

Islamorada is an ideal destination for family beach holidays and outdoor adventures. Visitors can explore a variety of attractions, including marinas, stunning beaches, and national parks. The area's points of interest cater to those seeking a blend of outdoor activities, cultural experiences, and relaxation by the sea, making it perfect for travellers looking to immerse themselves in both nature and local culture.

  • Anne's Beach: This idyllic beach offers a serene escape with its soft sands and gentle waves, perfect for sunbathing or a leisurely stroll. The picturesque setting is ideal for relaxing with a book or enjoying a picnic by the water.
  • Bud n' Mary's Dive Center: A hub for adventure enthusiasts, this marina provides thrilling diving and snorkelling experiences in the vibrant waters of the Florida Keys. It's perfect for exploring colourful coral reefs and diverse marine life.
  • Islamorada County Park: This urban park is a family-friendly oasis featuring playgrounds, picnic areas, and walking trails. It's an excellent spot for outdoor activities and enjoying quality time amidst the natural beauty of the area.

Things to do recommended for couples

For a romantic getaway in Islamorada, explore the underwater wonders with Florida Keys Dive Center, located eight miles away, perfect for adventurous couples. Afterwards, visit Rain Barrel Village for a charming shopping experience, soaking up the local atmosphere and vibrant vibes.

Things to do recommended for families

Families visiting Islamorada can enjoy a splashing good time at Jacob's Aquatic Center, an aquatic centre located 10.6km away. With its family-friendly atmosphere, it's the perfect spot for children to have fun while parents relax in the sun.

Things to do recommended for groups

Groups visiting Islamorada can savour craft beers at Florida Keys Brewing Co. and Islamorada Brewery & Distillery, both offering a lively atmosphere. Additionally, enjoy the vibrant ambience at Jimmy Johnson's Big Chill, located 10.6km away, perfect for a delightful evening out.

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

If you’re travelling with a group, family, pets, or seeking extended stays, be sure to filter according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Islamorada with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Islamorada with young kids: Traveling with young children can be quite a task. It's essential to prioritise 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, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Islamorada: If you're in search of holiday rentals with offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. You might also want to include options such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Islamorada

Islamorada, nestled in the stunning Florida Keys, offers an idyllic blend of relaxation and adventure for families and beach enthusiasts alike. From kayaking in crystal-clear waters to enjoying outdoor seating at charming eateries, this tropical paradise invites you to unwind. Explore the friendly atmosphere and romantic spots, all while soaking up the vibrant local culture. Whether you're seeking an oceanside retreat or a family-friendly getaway, Islamorada promises unforgettable experiences under the sun.

  • Tavernier: Tavernier is a charming city located 5.6km from Islamorada, known for its outdoor adventures and family-friendly atmosphere. This vibrant locale is ideal for those seeking a mix of relaxation and excitement. Visitors can enjoy various activities, including a range of resorts and shopping centres that cater to all tastes. Tavernier's prominent landmarks, such as the picturesque beaches and bustling tourist precinct, create an inviting environment for families and nature enthusiasts alike. Whether you’re lounging on the sandy shores or exploring local shops, Tavernier offers a delightful escape.
  • Venetian Shores: Nestled around the Islamorada area, Venetian Shores is a picturesque neighbourhood celebrated for its outdoor experiences and beautiful beaches. This serene enclave is perfect for families looking to unwind and enjoy the coastal lifestyle. With various shopping areas and recreational facilities, visitors can easily spend the day exploring local boutiques or engaging in water sports. The stunning beaches and family-friendly islands nearby provide a perfect backdrop for relaxation and fun, making Venetian Shores a must-visit destination for anyone travelling to the Florida Keys.
  • Lower Matecumbe Key: Lower Matecumbe Key, an enchanting island situated close to Islamorada, offers an idyllic beach experience for families and outdoor enthusiasts. This tranquil locale is known for its stunning natural beauty, with pristine beaches and lush landscapes beckoning visitors to explore. The area features a variety of resorts and recreational spots, ensuring that there’s something for everyone. Families can enjoy the sandy shores and vibrant island atmosphere, making Lower Matecumbe Key an ideal destination for a memorable getaway in 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Are you hoping to save on your upcoming holiday? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you might achieve substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to organise by price, location, and type of accommodation.

Vrbo Trips: Planning made easy

Vrbo’s innovative Trip Board offers you a dedicated space to plan new holidays, pick up where you last paused, and manage your travel arrangements effortlessly. You can easily locate the properties you’ve previously saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Travel to relaxing Islamorada

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

Sightseeing in and around Islamorada

Are you looking for attractions to see during your stay? Travellers enjoy fun activities like fishing and diving. Venture out of your cosy holiday rental and experience everything that Islamorada has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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

Travellers appreciate the beautiful ocean views and breathtaking sunsets, which is just a taste of what Islamorada has to offer. Whether you're an outdoor enthusiast or just want to take in the scenery, Islamorada is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport to and around Islamorada

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

Frequently asked questions

What is the best area to stay in Islamorada when booking a holiday 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 holiday rental here that's just right for you.
What is the most popular type of holiday rental accommodation in Islamorada?
Houses are the most popular style of holiday rental in Islamorada, according to our data. Even if you have a different idea about what you want, Vrbo has holiday homes in loads of sizes and shapes. Filter our options to find your perfect fit.
How much does it cost to rent a holiday rental in Islamorada?
Season, property type and length of stay are some things that can influence the price of a holiday home. Simply add your dates of travel to find your ideal escape. From homey country cottages to expansive villas, all Vrbo holiday 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 holiday 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 holiday 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 holiday 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 holiday rentals have the best amenities for chilling out with the people you cherish the most.
Are there large group holiday rentals in Islamorada?
You can pick from 18 holiday properties in Islamorada that can host a group of 10 or more guests. Whether you're organising 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 holiday rentals in Islamorada that welcome kids?
With 166 family-friendly holiday 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 travelling 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:

  • Theatre of the Sea
  • Annes Beach
  • Robbies

Are there one-bedroom holiday rentals in Islamorada?
Islamorada has 16 one-bedroom rentals on offer. Often positioned in popular areas due to their smaller size, a one-bedroom holiday 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 holiday 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 holiday rentals with WiFi in Islamorada?
Whether you want to keep up with world events, check emails or surf your social networks, there are 77 holiday homes with WiFi in Islamorada. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Islamorada?
Pick your dates and then make use of our filters to find holiday 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 holiday rental in Islamorada?
It's a good idea to check with the Islamorada holiday 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 holiday rental in Islamorada for?
The amount of time you can stay in an Islamorada holiday 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 holiday properties may also offer discounted weekly or monthly prices, so you can hang around longer for less.

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