Islamorada holiday rentals

We found 2,135 holiday rentals — enter your dates for availability

Select from 415 houses, 88 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:2 Oct - 9 Oct

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Why visit Islamorada

  • Stunning beaches: Enjoy the pristine shores of Islamorada, perfect for sunbathing and relaxation.
  • Vibrant coral reefs: Explore the rich marine life through snorkelling and diving adventures in the surrounding waters.
  • World-class fishing: Experience exceptional fishing opportunities, including deep-sea and backcountry fishing.
  • Rich history: Visit the fascinating History of Diving Museum to learn about the region's underwater heritage.
  • Charming local atmosphere: Discover delightful dining and shopping experiences in the quaint downtown area.

Popular types of accommodation in Islamorada

Islamorada, Florida, is a picturesque destination renowned for its stunning sunsets and vibrant marine life. Visitors can explore attractions like the History of Diving Museum, indulge in world-class fishing, or relax at pristine beaches. With a selection of private holiday homes, condos, and villas, finding the perfect Islamorada holiday rental is effortless. Enjoy the charm of this idyllic locale while experiencing everything it has to offer, from water sports to delightful dining options.

  • Private Holiday Homes: Enjoy a charming, self-contained dwelling offering privacy and comfort for your stay in Islamorada.
  • Condos: Experience modern, compact living in these well-appointed condominium spaces.
  • Villas: Relish in spacious, elegantly designed villas ideal for a relaxing break.
  • Apartments: Settle into cosy apartments providing practical amenities for a delightful retreat.
  • Caravan Parks: Embrace a unique holiday with caravan parks, offering an adventurous yet comfortable experience.**

Top attractions in Islamorada

Islamorada, Florida, offers a delightful blend of family-friendly and outdoor adventures. Enjoy pristine beaches, marinas, and state parks that provide a perfect backdrop for adventure and relaxation. Whether exploring local wildlife or simply soaking up the sun along the coast, visitors are sure to create lasting memories in this charming city.

  • Anne's Beach: A tranquil beach with stunning views, perfect for sunbathing and picnicking. This picturesque spot features shallow waters, making it ideal for families and those looking to relax in a serene environment.
  • Bud n' Mary's Dive Center: A hub for adventure enthusiasts, this marina offers diving and fishing excursions. Experience the vibrant marine life of the Florida Keys while enjoying the thrilling watersports available.
  • Islamorada County Park: A family-friendly urban park boasting green spaces, playgrounds, and recreational facilities. It's a great place for outdoor activities and leisurely strolls amidst nature.

Things to do recommended for couples

Discover a romantic getaway in Islamorada. Enjoy sunset boat rides, leisurely beach walks and intimate dining experiences, all perfect for a couple seeking a memorable holiday filled with local charm and enchanting moments.

Things to do recommended for families

Families can explore interactive marine exhibits at the Theatre of the Sea, savour local seafood delicacies, and enjoy a scenic picnic at Anne's Beach, experiencing Islamorada's family-friendly charm.

Things to do recommended for groups

Groups visiting Islamorada can enjoy a local fishing charter, explore the nearby coral reefs, and savour waterfront dining while experiencing the island’s unique art galleries and cultural shows.

*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

If you’re travelling with a group, as a family, bringing your pets, or seeking longer stays, it’s important to filter your options based on your specific priorities. Here are some helpful booking tips for using Stayz.

  • Traveling to Islamorada with a group: Consider how many bedrooms you’ll require, along with facilities like a fully equipped kitchen or an outdoor area for a group get-together. Fortunately, you can filter for all these, and more, on Stayz.
  • Traveling to Islamorada with young kids: Travelling with young children can present its challenges. It is essential to prioritise their comfort and safety, as well as look for age-appropriate facilities, such as a private swimming pool. Additionally, it’s wise to consider how close you are to family-friendly attractions.
  • Taking your pets with you to Islamorada: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Stayz properties that are pet-friendly. Most of these accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Islamorada: If you’re seeking holiday rentals offering deals for stays of a month or more, you’ve come to the right place. By applying the appropriate filters, you can effortlessly find and save on monthly rentals. Do consider including options such as 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 in the Florida Keys, perfect for families and outdoor enthusiasts. Visitors can unwind on its beautiful beaches, explore the vibrant coral reefs, and enjoy a variety of water sports. The charming downtown area offers delightful dining and shopping experiences, while the tranquil atmosphere ensures a relaxing getaway. With its unique blend of adventure and serenity, Islamorada truly captures the essence of a perfect holiday destination.

  • Tavernier: Situated a mere 14km from Islamorada, Tavernier is a charming city that offers an inviting blend of outdoor and family-friendly beach experiences. The area is celebrated for its sweeping coastal vistas and a variety of recreational pursuits. Visitors can enjoy a leisurely day at the beach or explore the local shopping precinct, which features a mix of modern retail centres and traditional shopping areas. The ambience here is relaxed and perfect for those looking to embrace a quintessential seaside holiday.
  • Venetian Shores: Nestled within the vicinity of Islamorada, Venetian Shores is a delightful neighbourhood known for its outdoor and family-oriented beach experiences. Its scenic setting provides an excellent backdrop for a range of activities, including adventure pursuits and educational ventures. The local attractions, such as the family beach and the picturesque island panorama, create a serene and stimulating environment, ideal for a leisurely exploration of natural beauty combined with light-hearted adventure.
  • Lower Matecumbe Key: Recognised as a naturally striking island, Lower Matecumbe Key lies in the heart of the Islamorada area. It is a haven for outdoor enthusiasts and families seeking a beach retreat. The locale offers a mix of adventure activities and underwater sporting opportunities, complemented by a recreational area that is perfect for a day out. The scenic beauty of the island is further enhanced by its pristine beaches and family-friendly atmosphere, making it a desirable destination for those looking to experience coastal living at its finest.

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 Stayz is a breeze

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as prices can fluctuate significantly. Furthermore, opting for an extended stay can often result in considerable savings. To discover the ideal Stayz property that fits within your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's Trip Board provides a dedicated area for you to plan new adventures, manage your existing arrangements, or revisit your bookings. The properties you've saved or reserved are conveniently organised into categories: Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/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)
  • Harry Harris Park (11 mi / 17.7 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 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, Stayz 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, Stayz 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 Stayz 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 Stayz. 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 Stayz. 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 Stayz. 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, Stayz 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 Stayz 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 Stayz. 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 Stayz 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 Stayz holiday properties may also offer discounted weekly or monthly prices, so you can hang around longer for less.