South Island holiday lettings

We found 1,134 holiday rentals — enter your dates for availability

Select from 46 houses, 208 flats and other holiday rentals to find the perfect place for your stay in South Island. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll find the amenities that you need and want, such as parking and air conditioning. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - South Island

Showing deals for:15 May - 22 May

Image gallery for Flip Flop Paradise - 3 Bdrms, Pool, Steps to the Beach

Beach
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Flip Flop Paradise - 3 Bdrms, Pool, Steps to the Beach

Fort Myers Beach

7% off
Price is £2,395
for 7 nights, 1 home
£342 per night
includes taxes & fees
Flip Flop Paradise - 3 Bdrms, Pool, Steps to the Beach

Find spaces that suit your style

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit South Island

  • Stunning beaches: South Island boasts beautiful sandy shores, perfect for sunbathing and beach activities.
  • Family-friendly atmosphere: The island offers a welcoming environment with numerous outdoor activities suitable for families.
  • Outdoor adventures: Engage in a variety of pursuits, from water sports to exploring local parks and attractions.
  • Charming accommodation: A range of holiday rentals is available, catering to diverse preferences and budgets.
  • Warm local hospitality: Experience the friendly nature of the locals, enhancing your holiday experience.

Popular types of accommodation around South Island

Vrbo offers a fantastic selection of holiday rentals on the South Island, perfect for any type of traveller. Whether you're seeking a private vacation home, a stylish condo, or a luxurious villa, we have the ideal holiday accommodation to suit your needs. Explore our range of holiday apartments and discover the perfect base for your adventures on this stunning island.

  • Houses: The top choice for visitors seeking a home-away-from-home experience, ideal for families and groups wanting privacy and space during their stay in South Island.
  • Condos: A popular option offering a blend of comfort and convenience, these self-contained units provide amenities like pools and beachfront access.
  • Villas: Elegant and spacious, villas are perfect for those looking for a touch of luxury and relaxation in a tranquil setting.
  • Apartments: A practical choice for solo travellers or couples, offering essential amenities in a compact and convenient layout.
  • Cottages: Quaint and charming, cottages provide a cosy retreat, perfect for a romantic getaway or a peaceful break.**

Top attractions near South Island

South Island in Fort Myers Beach is perfect for a beach holiday or outdoor family getaway. Visitors can enjoy a variety of attractions, including stunning beaches, urban parks, and modern universities, all catering to those seeking outdoor activities and family-friendly experiences. With plenty to explore, South Island promises a memorable vacation filled with sun and adventure.

  • Bonita Springs Public Beach: A stunning stretch of sandy beach offering a quintessential coastal experience with vibrant beach vibes, perfect for sunbathing, swimming, and enjoying water sports.
  • Florida Gulf Coast University: A contemporary university set in a vibrant city atmosphere, featuring beautiful grounds and a variety of cultural and educational events.
  • Hertz Arena: A lively entertainment venue that hosts concerts, sporting events, and family-friendly shows, ensuring a fun-filled outing for all ages.

Things to do recommended for couples

For a romantic getaway in South Island, consider a fun round of mini-golf at Jungle Golf Ft. Myers or Smugglers Cove Adventure Golf, both a mere 3.7km away. For a unique experience, dive into adventure at Sanibel Sea School, located 5.0km away.

Things to do recommended for families

Families visiting South Island can engage in various fun activities such as sporting events at Lee Health Sports Complex, exploring the wellness vibes at Mound Key Archaeological State Park, and enjoying arcade adventures at Beach Bowl, all within a short drive from your accommodation.

Things to do recommended for groups

Experience the vibrant Coconut Point Mall for shopping and entertainment, explore the cultural offerings at Barbara B Mann Hall, or enjoy a round of golf at Raptor Bay Golf Club, all within a short drive from South Island.

What do I need to keep in mind when booking a vacation around South Island

When travelling with a group, your family, pets, or if you're considering an extended stay, it’s important to apply the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to South Island with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to South Island with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with ensuring access to age-appropriate facilities, such as 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 South Island: For many, a family holiday wouldn’t be the same without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting South Island: If you're in search of holiday rentals with special offers 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 accommodations. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near South Island

South Island in Fort Myers Beach offers a delightful escape with its family-friendly atmosphere and stunning beaches. Visitors can enjoy a variety of outdoor activities, from relaxing on the sandy shores to exploring nearby attractions. With numerous holiday rentals and charming homes to choose from, you'll find the perfect base for your adventures. Immerse yourself in the warm hospitality of the locals and discover why this destination is ideal for a budget-friendly getaway.

  • Fort Myers Beach: Located a mere 2.5km from South Island, Fort Myers Beach is a vibrant seaside city renowned for its stunning sandy shores and family-friendly atmosphere. Visitors flock here to soak up the sun, indulge in water sports, and explore the local dining scene. With an array of resorts and recreation centres, there's something for everyone. Major attractions include the picturesque beach, where families can enjoy a day of fun in the sun, and the lively shopping mall centre, perfect for picking up souvenirs and enjoying local cuisine.
  • Sanibel: Situated 5.0km from South Island, Sanibel is famous for its pristine beaches and charming, laid-back vibe. This idyllic island city is a haven for families seeking outdoor adventures, with numerous recreational areas and resort options available. The beaches here are particularly noted for their shelling opportunities, making it a unique experience for visitors. Explore the stunning natural landscapes and enjoy the local shopping mall centre, where boutique shops and delightful eateries await.
  • Bonita Springs: Just 5.6km from South Island, Bonita Springs offers a delightful mix of beach relaxation and outdoor activities. This city is perfect for families looking to enjoy the sun, with excellent recreational centres and resorts available for all ages. You can also indulge in a round of golf at some of the area's top courses. The proximity to beautiful beaches and family-friendly attractions makes Bonita Springs an appealing destination for a memorable vacation.

Best time to go to South Island

If you're planning a trip to South Island, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January64.8°F (18.2°C)No Rain (Dry)Mostly SunnyHighAverage
February67.3°F (19.6°C)No Rain (Dry)SunnyHighAverage
March69.8°F (21.0°C)No Rain (Dry)SunnyHighSlightly High
April74.8°F (23.8°C)Light RainMostly SunnyAverageSlightly High
May78.6°F (25.9°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Moderate RainMostly SunnyAverageAverage
July83.5°F (28.6°C)Moderate RainMostly SunnyAverageAverage
August83.7°F (28.7°C)Moderate RainMostly SunnyLowSlightly Low
September82.2°F (27.9°C)Moderate RainMostly SunnyLowSlightly Low
October78.4°F (25.8°C)Light RainMostly SunnyLowSlightly Low
November72.5°F (22.5°C)No Rain (Dry)Mostly SunnyAverageAverage
December68.5°F (20.3°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a helpful platform for arranging your travel plans, allowing you to create new trips, resume from where you last stopped, or manage your itineraries with ease. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in South Island?
Prices for holiday rentals in South 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 South 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 South Island holiday house rentals?
You can find great discounts on house rentals in South 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 South Island holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in South 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.
Can I find long-stay holiday rentals in South Island?
A long-stay holiday rental in South 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.
When is the best time to visit South Island for a holiday rental?
The best time to visit South Island for a holiday rental is during the peak season from February to April, with March being particularly popular. This vibrant period attracts travellers eager to soak up the sun and enjoy the beautiful coastal scenery. With warm temperatures typically ranging from the low to mid-20s Celsius, March provides ideal conditions for outdoor activities such as swimming, boating, and exploring the stunning local beaches.

During these months, South Island buzzes with activity, offering a variety of events and attractions that cater to all interests. Whether you're lounging on the sandy shores or partaking in water sports, you'll find plenty of opportunities to create unforgettable memories.

For those looking to enjoy a quieter experience and potentially save on accommodation, consider visiting in October. This month offers a more relaxed atmosphere, making it superb for leisurely strolls along the beach and enjoying the natural beauty of the area without the summer crowds.

Ultimately, your choice of when to visit South Island will depend on whether you prefer the lively energy of peak season or the tranquil charm of the shoulder months.
How early should I book a South Island holiday rental?
Book your South 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.
What are the top attractions in South Island, Florida, United States of America?
In South Island, Florida, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The South Florida Museum, located nearby, offers insights into the region's history and ecology, featuring exhibits on local wildlife and marine life.

The charming beaches of Anna Maria Island provide a superb spot for sunbathing, swimming, and enjoying fresh seafood at local beachfront dining options.

For those interested in nature, the nearby Robinson Preserve features walking trails, kayaking opportunities, and birdwatching areas, making it a great place to immerse oneself in the local ecosystem.

The vibrant arts scene can be explored in the historic district of Bradenton, where visitors can find galleries, boutiques, and cultural events throughout the year.
Can I change or cancel my South Island home rental booking on Vrbo?
To find South 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the South 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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