Islamorada holiday homes

We found 2,132 holiday rentals — enter your dates for availability
Select from 414 houses, 90 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:30 Oct - 6 Nov

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Why visit Islamorada

  • Coastal adventures: Enjoy water-based activities, scenic coastal walks, and vibrant marina views.
  • Family-friendly fun: Explore outdoor adventures and beaches ideal for a relaxing family holiday.
  • Natural beauty: Hike through national and state parks showcasing picturesque island landscapes.
  • Water sports: Dive into thrilling water sports and aquatic escapades in tropical settings.
  • Tranquil escapes: Unwind on stunning beaches while embracing the island’s relaxed, inviting atmosphere.

Top attractions in Islamorada

Islamorada offers a memorable family-friendly holiday with plenty of outdoor and beach adventures. The city's stunning marina and inviting beach allow travellers to enjoy water-based activities and scenic coastal walks. National and state parks in the area provide ample opportunities for exploration and adventure, making Islamorada an ideal destination for those seeking a blend of relaxation and outdoor excitement. Whether you're travelling solo or with family, the vibrant local attractions await your discovery.

  • Bud n' Mary's Dive Center: Experience a vibrant marina with adventure and outdoor beach vibes, perfect for diving enthusiasts and those keen on exploring underwater wonders.
  • Anne's Beach: Enjoy a pristine stretch of beach with classic beach vibes, ideal for a relaxing day under the sun and a refreshing swim in the clear waters.
  • Islamorada County Park: Discover a family-friendly urban park with city charm and outdoor flair, offering a welcoming space for picnics and leisurely strolls.

Things to do recommended for couples

Islamorada offers a perfect romantic getaway. Enjoy a sunset sail on the turquoise waters or indulge in a candlelit dinner at a beachfront restaurant. Explore the scenic paths of the Florida Keys or go for a couple's spa day, immersing yourselves in relaxation and tranquility.

Things to do recommended for families

Families visiting Islamorada can explore the fascinating Florida Keys History & Discovery Center, enjoy a day of fun at Founders Park with its playground and beach, or go on an exciting eco-tour to spot dolphins and manatees in their natural habitat.

Things to do recommended for groups

Groups visiting Islamorada can embark on a thrilling glass-bottom boat tour to explore vibrant coral reefs, enjoy a sunset fishing trip, and indulge in fresh seafood at local eateries, all while soaking in the stunning Florida Keys scenery.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When you’re planning a trip—be it with a group, family, or pets, or if you’re considering an extended stay—be sure to refine your search 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'll require, as well as features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Islamorada with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with ensuring access to age-appropriate facilities 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 isn’t complete without the inclusion of their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring a cosy stay for every member of the family.
  • Planning for a long term stay visiting Islamorada: If you're searching for holiday rentals with discounts for stays of a month or more, 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 include preferences like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Islamorada

Islamorada, Florida, is a picturesque island paradise perfect for families and outdoor enthusiasts. Visitors can enjoy stunning beaches, ideal for relaxation and fun-filled days in the sun. Explore scenic hiking trails that showcase the area's natural beauty, or indulge in thrilling water sports. With a friendly atmosphere and romantic vibes, Islamorada offers a perfect getaway for those seeking adventure or a tranquil escape in a tropical setting.

  • Tavernier: Tavernier is a vibrant city located 14km from Islamorada, offering visitors a delightful blend of outdoor activities and family-friendly experiences. This charming locale is perfect for those seeking a beach getaway, with easy access to stunning shores and a lively tourist precinct. Enjoy shopping at the local mall or explore the various shops and eateries in the area. Tavernier’s inviting beaches are ideal for a day of relaxation or fun in the sun, making it a fantastic destination for families and beach lovers alike.
  • Lower Matecumbe Key: Situated in close proximity to Islamorada, Lower Matecumbe Key is a picturesque island known for its abundant outdoor activities and beautiful beaches. Visitors flock here for adventure, whether it’s diving into the vibrant underwater world or enjoying a variety of recreational pursuits. The island offers stunning family beaches that are perfect for sunbathing, swimming, and building sandcastles. With its natural beauty and serene atmosphere, Lower Matecumbe Key provides an idyllic setting for both relaxation and adventure.
  • Plantation Key: Located 10km from Islamorada, Plantation Key is another enchanting island that attracts visitors with its outdoor offerings and family-friendly environment. The area features a shopping mall centre for those who enjoy retail therapy, as well as scenic golf courses for golf enthusiasts. The inviting beaches and lush surroundings make Plantation Key an excellent choice for families looking to spend quality time together. Whether you’re sunbathing on the beach or enjoying a round of golf, this charming island has something for everyone.

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.

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

Booking with Vrbo is simple

Looking to cut costs on your next journey? You might consider being flexible with your travel dates since prices do vary. In addition, booking a longer stay can often lead to significant savings. To find the ideal Vrbo rental that suits your budget, simply use our filters to sort by price, location, and type of holiday accommodation.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a handy place to plan new adventures, continue from where you last stopped, or review and arrange your travel plans. You'll see your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, head over to: https://www.bookabach.co.nz/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:

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

  • 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)
  • Windley Key Fossil Reef Geological State Park (2.4 mi / 3.8 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 home?
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, Bookabach is sure to have a holiday home here that's just right for you.
What is the most popular type of holiday home accommodation in Islamorada?
Houses are the most popular style of holiday home in Islamorada, according to our data. Even if you have a different idea about what you want, Bookabach 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 home 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 Bookabach holiday homes 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 Bookabach. 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 homes 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 homes on Bookabach. 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 Bookabach. 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 home amenities in Islamorada?
Some of the most popular home 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, Bookabach holiday homes have the best amenities for chilling out with the people you cherish the most.
Are there large group holiday homes 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 homes in Islamorada that welcome kids?
With 166 family-friendly holiday homes 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 homes in Islamorada?
Islamorada has 16 one-bedroom homes on offer. Often positioned in popular areas due to their smaller size, a one-bedroom holiday home 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 homes 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 homes 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 Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Islamorada?
Pick your dates and then make use of our filters to find holiday homes with air conditioning in Islamorada on Bookabach. 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 home in Islamorada?
It's a good idea to check with the Islamorada holiday property you're considering on Bookabach as the minimum age varies. However, normally it's 16, 18 or 21.
How long can I rent a holiday home in Islamorada for?
The amount of time you can stay in an Islamorada holiday home 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 Bookabach holiday properties may also offer discounted weekly or monthly prices, so you can hang around longer for less.