Photo by Ash Feky

Fleming Island holiday lettings

We found 418 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Fleming Island that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Fleming Island

Showing deals for:2 Jan - 9 Jan
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Find out more about Fleming Island

Find out more about Fleming Island

Why visit Fleming Island

  • Outdoor Adventures: Fleming Island is ideal for nature lovers, offering various parks and scenic spots for relaxation and activities.
  • Family-Friendly Activities: The destination caters to families with engaging options suitable for all ages, ensuring a fun-filled experience.
  • Charming Local Neighbourhoods: Explore the delightful local areas, featuring unique shops and eateries that reflect the island's character.
  • Varied Accommodation: A range of holiday rentals, from cosy condos to spacious homes, provides the perfect base for your stay.
  • Nearby City Vibe: Enjoy the lively atmosphere of nearby cities, perfect for those seeking a touch of urban excitement.

Popular types of accommodation in Fleming Island

Vrbo offers a delightful selection of vacation rentals in Fleming Island, perfect for your holiday escape. Whether you're seeking a charming private holiday home, a modern apartment, or a cosy condo, we have options to suit every traveller. From spacious Fleming Island house rentals to intimate flats, discover the ideal accommodation for your getaway. Your perfect Fleming Island home awaits!

  • Houses: The most sought-after option for holiday rentals in Fleming Island, offering a spacious and comfortable environment for families and groups.
  • Condos: A popular choice, providing modern amenities and often stunning views, ideal for couples or small families.
  • Apartments: A convenient option for those seeking flexibility and a homely atmosphere during their stay.
  • Cottages: Quaint and charming, these are perfect for a peaceful retreat in a picturesque setting.
  • Villas: Luxurious accommodations that offer an upscale experience with ample space and private amenities.**

Top attractions in and around Fleming Island

Fleming Island is an excellent destination for outdoor enthusiasts, families, and city explorers alike. Visitors can enjoy a variety of attractions, including urban parks, marinas, and the beautiful island scenery. Whether you're seeking a relaxing day out or engaging activities, Fleming Island offers a delightful mix of experiences to suit all travellers.

  • Clay County Fairgrounds: Located 3.1km from Fleming Island, this vibrant fairground offers a delightful outdoor atmosphere perfect for families. Enjoy various events and activities that embody the spirit of community and fun.
  • The Golf Club At Fleming Island: Nestled within Fleming Island, this welcoming golf club caters to families, businesses, and romantic outings. Experience beautiful greens and friendly service, making it an ideal spot for relaxation and recreation.
  • Mandarin Museum: Situated 3.7km from Fleming Island, this charming museum immerses visitors in local history and culture. Explore exhibits that celebrate the area's rich heritage and enjoy a tranquil setting.

Things to do recommended for couples

For a romantic getaway in Fleming Island, indulge in the luxury of San Jose Country Club, just 7.5km away, or enjoy the serene atmosphere at Magnolia Point Golf and Country Club, a mere 3.7km from your base. Both offer a perfect setting for couples to unwind together.

Things to do recommended for families

Families visiting Fleming Island can unwind at Westside Regional Park, just 5.6km away, enjoying its serene atmosphere. For a dose of excitement, Latitude 30 offers an adventure-filled arcade experience, 7.5km away, while Stockton Park provides another relaxing retreat, also 7.5km from Fleming Island.

Things to do recommended for groups

Groups visiting Fleming Island can enjoy shopping at the Orange Park Mall, just 3.7km away, experience outdoor sports at Eagle Harbor Golf Club, and explore the cultural charm of the Strand Theater Site, located 6.2km from Fleming Island, perfect for family and romantic outings.

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

If you're travelling with a group, with family, bringing your pets, or seeking extended stays, be sure to use the appropriate filters to suit your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Fleming Island with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily refine your search to include these options and much more on Vrbo.
  • Traveling to Fleming Island with young kids: Travelling with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Fleming Island: For many families, a getaway wouldn’t be the same without their beloved pet. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Fleming Island: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don't forget to include features such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Fleming Island

Fleming Island, Florida, offers a delightful blend of outdoor adventures and family-friendly activities. Visitors can explore the charming local neighbourhoods, enjoy the tranquil atmosphere, and partake in various outdoor pursuits. Nearby cities provide a lively vibe, perfect for those seeking relaxation or a touch of romance. Whether you're wandering through scenic parks or indulging in local cuisine, Fleming Island promises a memorable experience for every type of traveller.

  • Lakeside: Situated a mere 2.5km from Fleming Island, Lakeside is a vibrant neighbourhood that offers a delightful family-friendly atmosphere. Visitors can enjoy a variety of outdoor experiences, from exploring local parks to unwinding at nearby lakes. The area boasts convenient access to a shopping centre and a shopping mall, making it a great spot for retail therapy. For those seeking leisure, a resort in the vicinity provides relaxation options. Key attractions include a theme park and beautiful beaches, perfect for a day out with the family.
  • Orange Park: Located 3.1km away from Fleming Island, Orange Park is a bustling city that caters to families and business travellers alike. This destination features a variety of shopping venues, including a large shopping mall and centre, ensuring that visitors have plenty of options for dining and retail. Orange Park also offers access to exciting attractions such as a local beach, a theme park, and a stadium, making it an ideal spot for both leisure and entertainment. The city's blend of urban and natural experiences makes it a must-visit on your journey.
  • Fruit Cove: Just 3.1km from Fleming Island, the charming neighbourhood of Fruit Cove is a haven for outdoor enthusiasts and sports lovers. The area is home to several golf courses, providing ample opportunities for a round of golf in a picturesque setting. Visitors can also enjoy a variety of recreational activities at the local resorts. Notable attractions nearby include a sports museum, a beautiful beach, and an urban park where families can relax and enjoy nature. Fruit Cove offers a delightful mix of leisure, sport, and family-friendly activities.

Best time to go to Fleming Island

If you're planning a trip to Fleming Island, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in February, April and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January56.1°F (13.4°C)Light RainMostly SunnyAverageSlightly Low
February59.9°F (15.5°C)Light RainMostly SunnySlightly HighSlightly Low
March64.4°F (18.0°C)Light RainMostly SunnyAverageAverage
April70.3°F (21.3°C)Light RainMostly SunnySlightly HighAverage
May75.7°F (24.3°C)Light RainMostly SunnyAverageAverage
June80.6°F (27.0°C)Light RainMostly SunnyAverageSlightly High
July82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly High
August82.2°F (27.9°C)Light RainMostly SunnyAverageAverage
September79.3°F (26.3°C)Light RainMostly SunnySlightly HighSlightly Low
October72.9°F (22.7°C)Light RainMostly SunnySlightly LowAverage
November64.6°F (18.1°C)Light RainMostly SunnySlightly LowAverage
December60.3°F (15.7°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to cut costs on your next getaway? It might be worth considering some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo accommodation that fits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board provides you with a dedicated area to plan fresh adventures, pick up from where you last stopped, or manage your travel arrangements effectively. You can easily access the properties you've saved or booked, now conveniently sorted into Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The captivating area of Fleming Island awaits your stay

Enjoy the entertainment and other features of Fleming Island. This city's football games, restaurants and shopping attract many visitors, as does its romantic and scenic location. Jacksonville Naval Air Station and St. Johns Town Center are just a couple of the must-see attractions in the area. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Fleming Island

Are you hoping to find things to do in the city? Venture out of your cosy holiday rental and check out everything that makes Fleming Island a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Eagle Harbor Golf Club (1.4 mi / 2.3 km)
  • The Champions Club at Julington Creek (6.6 mi / 10.6 km)
  • Golf Club at South Hampton (10.7 mi / 17.2 km)
  • St. John's Golf and Country Club (12.9 mi / 20.7 km)
  • World Golf Village - King & Bear Golf Course (15.2 mi / 24.4 km)
  • World Golf Village (16.5 mi / 26.5 km)

Exploring the natural features in Fleming Island

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Fleming Island is a great spot to appreciate mother nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Clay County Fairgrounds (4.8 mi / 7.7 km)
  • Spring Park (7.3 mi / 11.8 km)
  • Dog Wood Park of Jacksonville (13.2 mi / 21.2 km)
  • Cummer Museum of Art and Gardens (15.5 mi / 25 km)
  • Crystal Springs Park (15.9 mi / 25.5 km)
  • Metropolitan Park (16.4 mi / 26.3 km)

Transport to and around Fleming Island

The nearest airport is in Jacksonville, FL (CRG-Jacksonville Executive at Craig), located 20.7 mi (33.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to St. Augustine, FL (UST-Northeast Florida Regional), which is 24 mi (38.6 km) away.

Frequently asked questions

What is the best area to stay in Fleming Island when booking a holiday rental?
When considering a holiday rental in Fleming Island, Florida, the best area to stay is the northern part of the island, particularly near the scenic waterfront along the St. Johns River. This region boasts a charming atmosphere, with a variety of properties available, ranging from modern homes to quaint cottages, offering ample choices for families and couples alike.

Staying in the northern section allows easy access to the beautiful Fleming Island Marina, where you can enjoy water activities or simply take in the picturesque views. Another highlight in this area is the popular Doctor's Lake, great for those who appreciate nature and outdoor pursuits. You can often find walking trails and parks nearby, making it an ideal spot for leisurely strolls or picnics.

The southern part of Fleming Island is also delightful, featuring the much-loved Fleming Island Plantation. This neighbourhood is known for its lush landscaping and proximity to golf courses, which can be a fantastic draw for golf enthusiasts. The local shops and restaurants here add to the appeal, providing a vibrant community feel while ensuring you have everything you need within reach.
How much does it cost to rent a holiday home in Fleming Island?
Prices for holiday rentals in Fleming Island 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Fleming Island to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Fleming Island holiday house rentals?
You can find great discounts on house rentals in Fleming Island 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.
Are there any houseboat rentals in Fleming Island?
In Fleming Island, there are several houseboat holiday rentals available, providing a unique and charming way to experience the area's waterways. These houseboats typically offer amenities such as comfortable sleeping quarters, kitchen facilities for self-catering, and outdoor decks that allow guests to relax while enjoying picturesque views of the St. Johns River. Many rentals are located near local attractions, including parks, marinas, and restaurants, making it easy for travellers to explore the vibrant surroundings.
What is the most popular type of holiday rental accomodation in Fleming Island?
In Fleming Island, holiday houses are the most popular type of rental accommodation, with several available throughout the area. These properties typically offer spacious living environments, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas such as patios or decks, superb for enjoying the warm Florida weather. Many houses are located in family-friendly neighbourhoods, providing a serene atmosphere for relaxation after exploring local attractions. Apartments are also available, providing a more compact option for couples or solo travellers, usually equipped with essential amenities. Additionally, houseboats can be found for those seeking a great experience on the water, offering a different perspective of the beautiful surroundings.
Are there any family house rentals in Fleming Island?
In Fleming Island, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This community, known for its picturesque surroundings and access to the St. Johns River, offers spacious homes that often include features like full kitchens for meal preparation, large living areas for family gatherings, and outdoor patios where kids can play.
Can I find long-stay holiday rentals in Fleming Island?
A long-stay holiday rental in Fleming Island 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 Fleming Island?
In Fleming Island, there are several pet-friendly house rentals available that are superb for families and pet owners. Many of these holiday homes typically offer spacious living areas, fully equipped kitchens, and outdoor spaces such as backyards or patios where pets can roam freely.
Are there any remote work holiday rentals in Fleming Island?
In Fleming Island, there are several remote work holiday rentals available, making it an excellent choice for those looking to combine work and leisure. Many of these properties are designed with remote work in mind, featuring dedicated office spaces complete with desks and comfortable chairs. Additionally, Wi-Fi is typically provided to ensure seamless connectivity for business needs. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Fleming Island holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Fleming Island 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 Fleming Island?
In Fleming Island, holiday rentals commonly feature a variety of amenities that enhance the comfort of travellers. Most properties come equipped with kitchens, allowing guests to prepare their own meals, which is particularly convenient for families or those wanting to save on dining out. Cookware, dishware, and utensils are typically provided as part of the kitchen setup. Additionally, many rentals offer free Wi-Fi, ensuring that guests can stay connected during their stay. Outdoor spaces are also a highlight, with patios available for relaxing in the pleasant Florida weather. Coffee makers are often included as well, making it easy for guests to enjoy a fresh brew in the morning.
When is the best time to visit Fleming Island for a holiday rental?
September is a popular time to visit Fleming Island, Florida, as temperatures begin to cool slightly, offering a pleasant climate for outdoor activities. This month sees visitors enjoying the natural beauty of the area, with opportunities for kayaking, fishing, and exploring the nearby parks, all set against the backdrop of the picturesque St. Johns River.

The peak season for holiday rentals typically spans from February to April, when tourists flock to the area to escape colder climates and take advantage of the warm, sunny weather. During this period, visitors can enjoy a variety of outdoor pursuits, from golfing to hiking through the scenic landscapes, all while enjoying comfortable temperatures averaging in the mid to high 20s Celsius.

For those seeking a more budget-friendly option, November presents an ideal opportunity to experience Fleming Island without the crowds. This quieter month offers a unique charm as the weather remains mild, great for leisurely strolls along the river and enjoying the local cuisine at outdoor cafés.
How early should I book a Fleming Island holiday rental?
Book your Fleming Island holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Fleming Island home rental booking on Vrbo?
To find Fleming Island holiday 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 Fleming Island holiday 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.

More holiday ideas

More holiday ideas