South Island holiday lettings

We found 934 holiday rentals — enter your dates for availability

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September 2025

October 2025

Select from 132 houses, 856 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:26 Dec - 2 Jan

Wonderful

(16 reviews)

5545 New 4BR Oasis: Walk to Beach, Pool, Pet-Friendly!

Fort Myers Beach, FL

6% off

for 7 nights, 1 home

£914 per night

includes taxes & fees

Exceptional

(56 reviews)

Steps to the sugar sand beach of Fort Myers Beach! Peaceful setting

Fort Myers Beach, FL

7% off

for 7 nights, 1 apartment

£288 per night

includes taxes & fees

Exceptional

(5 reviews)

Bella Vie on Ft Myers Beach with 4 min walk to beach, lanai, pool, & gym

Fort Myers Beach, FL

7% off

for 7 nights, 1 apartment

£465 per night

includes taxes & fees

Exceptional

(8 reviews)

Luxury 3 Bed 2 Bath in FMB! Beach & Pool with the BEST reviews!

Fort Myers Beach, FL

7% off

for 7 nights, 1 apartment

£436 per night

includes taxes & fees

Wonderful

(17 reviews)

Beautiful Penthouse 2 Bed Plus Den with Pull Out Sleeper Steps From Beach

Fort Myers Beach, FL

7% off

for 7 nights, 1 apartment

£322 per night

includes taxes & fees

Front entrance to Estero Beach & Tennis Club

Wonderful

(68 reviews)

Estero Beach & Tennis Club Completely renovated January 2024

Fort Myers Beach, FL

8% off

for 7 nights, 1 apartment

£228 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in South Island

Castle Beach

Find the best place to stay - South Island

Yachts and Villas By the Bay

Sleeps 6 · 2 bedrooms · 2+ bathrooms

Premier Host

Santa Maria Resort- Great Resort and Condo!! Large refurbished pool & hot tub!

Sleeps 8 · 3 bedrooms · 2 bathrooms

Top rated rentals - South Island

Premier Host

Perfect for a quiet holiday

Perfection if you want a quiet and very comfortable vacation. Hosts are excellent to deal with and communicate promptly and effectively. The apartment has everything required. Located in a peaceful area of Fort Myers beach. We loved it.

Russell W.

Stayed Jun 2024

Peace of mind
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

Find out more about South Island

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	64.8°F (18.2°C)	No Rain (Dry)	Mostly Sunny	High	Average
February	67.3°F (19.6°C)	No Rain (Dry)	Sunny	High	Average
March	69.8°F (21.0°C)	No Rain (Dry)	Sunny	High	Slightly High
April	74.8°F (23.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
May	78.6°F (25.9°C)	Light Rain	Mostly Sunny	Average	Average
June	82.0°F (27.8°C)	Moderate Rain	Mostly Sunny	Average	Average
July	83.5°F (28.6°C)	Moderate Rain	Mostly Sunny	Average	Average
August	83.7°F (28.7°C)	Moderate Rain	Mostly Sunny	Low	Slightly Low
September	82.2°F (27.9°C)	Moderate Rain	Mostly Sunny	Low	Slightly Low
October	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Low	Slightly Low
November	72.5°F (22.5°C)	No Rain (Dry)	Mostly Sunny	Average	Average
December	68.5°F (20.3°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly 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

What is the most popular type of holiday rental in South Island?

In South Island, condos are the most popular type of holiday rental, with around 592 available in attractive locations near the coastline and local amenities. These condos typically feature modern designs, fully equipped kitchens, spacious living areas, and private balconies that offer stunning views of the beach or surrounding landscape.

Are there any beach house rentals in South Island?

In South Island, Florida, there is a substantial selection of beach house rentals, with approximately 1,935 available across the area. These beach houses are typically found in picturesque neighbourhoods with stunning views of the Gulf of Mexico and easy access to local attractions such as Bowman's Beach and the J.N. "Ding" Darling National Wildlife Refuge.

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?

March is the most popular month to visit South Island, Florida, as it marks the peak of the tourist season, which generally spans from February to April. This time of year attracts travellers seeking sun-soaked beaches, vibrant local culture, and a host of outdoor activities. With average temperatures in the mid-20s Celsius, it's superb for enjoying the area's beautiful coastline and participating in watersports like kayaking and paddleboarding.

During this peak season, expect an energetic atmosphere filled with tourists keen to explore the local attractions, such as the stunning Everglades National Park and the charming shops and restaurants of nearby communities. The weather is ideally suited for outdoor pursuits, making it comfortable for everything from lazy beach days to active sightseeing.

For those looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience, allowing you to enjoy the beautiful fall weather and fewer crowds while still indulging in the area's natural beauty. It's a wonderful time for leisurely walks along the shore and exploring the local parks without the hustle and bustle of peak tourist traffic.

Are there any remote work holiday rentals in South Island?

In South Island, Florida, there are numerous remote work holiday rentals available, with around 633 options to choose from. This vibrant area is superb for those looking to blend work and leisure, offering a range of properties equipped with essential amenities for remote work. Travellers can expect rentals featuring dedicated workspaces, comfortable desk chairs, high-speed Wi-Fi, and even larger setups with computer monitors for an optimal work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.

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.

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 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 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.