South Island vacation rentals

We found 1,132 vacation rentals — enter your dates for availability

Select from 46 houses, 208 condos, and other vacation rentals to find the perfect place for your stay in South Island. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll find the amenities you need and want, such as WiFi and cable TV. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - South Island

Showing deals for:May 15 - May 22

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

8% off
Price is $411
$2,880 for 7 nights
All fees included
Flip Flop Paradise - 3 Bdrms, Pool, Steps to the Beach

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Find out more about South Island

Why visit South Island

  • Beautiful Beaches: South Island boasts stunning sandy beaches perfect for sunbathing, swimming, and beachcombing.
  • Outdoor Adventures: Enjoy various outdoor activities such as kayaking, fishing, and hiking in picturesque parks.
  • Family-Friendly Atmosphere: The area offers numerous attractions and activities suitable for visitors of all ages, making it ideal for family vacations.
  • Charming Local Community: Experience the warm hospitality of friendly locals who enhance your visit with their welcoming spirit.
  • Diverse Accommodation Options: Choose from a range of vacation rentals, including cozy beach homes and spacious condos.

Popular types of accommodation around South Island

Planning a getaway to South Island? You're in for a treat. Discover the most sought-after vacation rentals, including houses, condos, and villas. Whether you’re looking for a cozy beach access retreat or a spacious family-friendly home, South Island has something for everyone. Explore your options and enjoy a memorable stay in South Island, where relaxation and adventure await.

  • Houses: The top choice for visitors to South Island, these homes offer spacious and comfortable accommodations perfect for families or groups.
  • Condos: A popular option, condos provide amenities and proximity to the beach, making them ideal for a laid-back vacation.
  • Villas: These luxurious properties offer upscale living spaces and often include private pools and stunning views.
  • Apartments: A practical choice, apartments are great for couples or solo travelers seeking convenience and comfort.
  • Cottages: Charming and cozy, cottages provide an inviting atmosphere for a peaceful getaway.**

Top attractions near South Island

South Island, located in Fort Myers Beach, Florida, is perfect for beach and outdoor family vacations. Visitors can explore a variety of attractions, including beautiful beaches, urban parks, and modern colleges. With its focus on outdoor activities and family-friendly experiences, South Island offers a delightful getaway for travelers seeking relaxation and adventure amidst stunning natural surroundings.

  • Bonita Springs Public Beach: A picturesque beach with soft sand and vibrant beach vibes, perfect for sunbathing, swimming, and enjoying stunning sunsets. Located 5 miles from South Island, it’s an ideal spot for relaxation and beach activities.
  • Florida Gulf Coast University: A modern campus that exudes city vibes, just 9 miles away from South Island. Explore its beautiful grounds, engage with students, or attend various events held throughout the year.
  • Hertz Arena: An entertainment hub located 8 miles from South Island, offering family-friendly events, concerts, and sports. Experience the lively atmosphere and enjoy a variety of entertainment options.

Things to do recommended for couples

For a romantic getaway in South Island, explore Jungle Golf Ft. Myers and Smugglers Cove Adventure Golf for some fun mini-golfing, both just 6 miles away. Don't miss the Sanibel Sea School, located 8 miles away, for an adventurous underwater experience together.

Things to do recommended for families

Your family will have a blast at the Lee Health Sports Complex, just 9 miles away, perfect for sports enthusiasts. Explore wellness at Mound Key Archaeological State Park, only 2 miles away, or unwind at Bay Oaks Recreation Center, located 3 miles from South Island. Enjoy your adventure.

Things to do recommended for groups

Groups visiting South Island can enjoy shopping and entertainment at Coconut Point Mall, just 6 miles away. Experience culture and romance at Barbara B Mann Hall, 9 miles from South Island, or hit the greens at Raptor Bay Golf Club, located 4 miles away for a fun day outdoors.

*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 around South Island

When planning your trip—whether you're traveling with friends, family, bringing pets, or seeking extended stays—be sure to prioritize your preferences while filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to South Island with a group: Think about how many bedrooms you'll require, as well as any amenities that might be important, like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these features and more on Vrbo.
  • Traveling to South Island with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities 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 South Island: For many families, a vacation isn't truly fulfilling without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting South Island: If you're in search of vacation rentals that offer special rates 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 consider adding options like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay near South Island

South Island, located in Fort Myers Beach, Florida, offers a delightful vacation experience filled with sunshine, sandy beaches, and family-friendly activities. This charming neighborhood is perfect for relaxing excursions, where friendly locals welcome visitors to explore the beautiful coastline and outdoor adventures. Nearby attractions enhance your Florida vacation, ensuring memorable moments for everyone. Discover the captivating atmosphere and make the most of your visit to this enchanting slice of paradise.

  • Fort Myers Beach: Nestled on the stunning Gulf Coast, Fort Myers Beach is a vibrant city known for its picturesque shoreline and family-friendly atmosphere. South Island is part of this charming locale, where visitors can enjoy a plethora of beach activities, from sunbathing to water sports. The area boasts numerous resorts and recreational centers, making it an ideal destination for those seeking relaxation and adventure. Don’t miss the chance to explore the local shops and indulge in delicious seafood at waterfront restaurants. The pristine beaches are perfect for family outings, ensuring memorable experiences for all ages.
  • Sanibel: Just 8 miles from South Island, Sanibel is a serene island paradise famous for its shell-strewn beaches and laid-back vibe. This city offers a perfect blend of outdoor activities and family entertainment. Visitors can explore the beautiful beaches, visit the J.N. Ding Darling National Wildlife Refuge, or enjoy the quaint shops and eateries in the area. Sanibel is also home to several resorts and recreational areas, making it easy to unwind and soak up the sun. The natural beauty and wildlife make it a must-visit for nature lovers and families alike.
  • Bonita Springs: Located 9 miles from South Island, Bonita Springs is a hidden gem that offers a rich array of outdoor experiences. This city is renowned for its lovely beaches, golf courses, and recreational centers. Perfect for families, Bonita Springs provides ample opportunities for fun, whether it's enjoying a day on the beach or hitting the links at one of the local golf courses. Visitors can also explore the scenic parks and indulge in the vibrant dining scene. With its welcoming atmosphere and numerous attractions, Bonita Springs is a delightful addition to your vacation itinerary.

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. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your total booking. Being the planner truly pays off. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on applicable reservations. Sign up today and start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's unique Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or easily view and manage your travel arrangements. You can conveniently find your saved and booked properties in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in South Island?
In South Island, condos are the most popular type of vacation rental, with about 782 available throughout the area. These condos are typically situated in vibrant neighborhoods, offering easy access to local attractions and beautiful beaches. Most units come equipped with modern amenities, including fully stocked kitchens, comfortable living spaces, and often private balconies to enjoy the scenic views.

For those seeking more space, there are around 106 vacation houses available, which usually feature multiple bedrooms, spacious living areas, and outdoor spaces ideal for gatherings. Additionally, there are around 49 apartments, alongside several villas and cottages, providing a diverse range of options to cater to different preferences and group sizes.
Are there any beach house rentals in South Island?
In South Island, there are approximately 2,146 beach house rentals available, making it a popular destination for travelers seeking a coastal getaway. These beach houses are typically situated near the shore, providing easy access to the beach and stunning ocean views. Travelers can expect a variety of amenities, including spacious layouts with multiple bedrooms, fully equipped kitchens for preparing meals, and outdoor spaces such as patios or decks for relaxing in the sun. Many properties also come with features like private pools, hot tubs, and direct beach access, suiting families and groups looking for a comfortable and enjoyable vacation experience.
How much does it cost to rent a vacation home in South Island?
Prices for vacation 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 vacation 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.
What are popular rental amenities in South Island?
In South Island, Florida, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals, and balconies that provide a lovely spot to enjoy the warm weather and views. Many rentals also offer onsite parking, making it convenient for travelers with vehicles. Additionally, guests can expect coffee and tea makers to enjoy their morning brews, and shared pools are a common feature, superb for cooling off and relaxing after a day of exploring the beautiful surroundings.
Can I find family house rentals in South Island?
In South Island, Florida, there are a substantial number of family-friendly house rentals available, totaling around 657. This area is known for its inviting atmosphere and proximity to beautiful beaches, making it an excellent choice for families. Properties in neighborhoods like South Beach and the vicinity of the Intracoastal Waterway often feature spacious living areas, fully equipped kitchens for convenient meal preparation, and outdoor spaces ideal for relaxation and play.

Families can enjoy amenities such as private pools, game rooms, and easy access to local attractions. Nearby points of interest include parks with playgrounds and walking trails, ensuring that there are plenty of activities to keep kids entertained.
Can I rent a vacation home with a pool or hot tub in South Island?
In South Island, Florida, there are plenty of vacation homes available for rent that come with pools and hot tubs, with around 796 options featuring pools and 192 with hot tubs. This region offers a mix of charming waterfront properties and cozy homes located in residential neighborhoods. Travelers can expect a variety of amenities in these rentals, including private swimming pools, relaxing hot tubs, spacious outdoor areas for entertaining, and fully equipped kitchens, making them great for family gatherings or romantic getaways.
Are there any South Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in South Island with parking available—perfect for families or travelers 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 book pet-friendly vacation rentals in South Island?
In South Island, Florida, travelers can find a variety of pet-friendly vacation rentals, with approximately 248 options available. These rentals typically offer amenities such as spacious living areas, fully equipped kitchens, outdoor patios, and sometimes private pools, making them suitable for families and groups traveling with pets. The area is known for its beautiful beaches and outdoor recreational activities, providing plenty of opportunities for pet owners to enjoy time with their furry friends. Nearby parks and nature trails offer great places to walk and explore, ensuring a pleasant experience for both pets and their owners.
Can I find long-stay vacation rentals in South Island?
A long-stay vacation rental in South Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit South Island for a vacation rental?
The best time to visit South Island for a vacation rental is during the peak season from February to April, with March being particularly popular among travelers. This period is characterized by warm temperatures, generally ranging from the mid-60s to low 80s Fahrenheit, making it ideal for outdoor activities like beach lounging and water sports. Visitors can enjoy the beautiful coastline and vibrant local festivals, creating an energetic atmosphere that enhances the experience.

During these months, the area attracts a bustling crowd, especially families and adventure enthusiasts seeking sun-soaked days and memorable experiences. The pleasant weather and lively ambiance make it a prime time for sightseeing, exploring nature trails, and indulging in local cuisine at beachfront restaurants.

If you're looking for a more budget-friendly option, consider visiting in October. While it may be less crowded, this month still offers beautiful weather and the chance to enjoy the region's natural beauty without the peak season hustle. It's a wonderful time for leisurely strolls along the shoreline and discovering hidden gems in the area.
Are there any remote work vacation rentals in South Island?
In South Island, Florida, there are numerous options for remote work vacation rentals, with around 827 available across the area. Many of these properties are designed to accommodate working travelers, featuring essential amenities like free Wi-Fi, dedicated workspaces, and comfortable living areas that make it easy to balance work and leisure.

Travelers can expect a variety of accommodations, ranging from cozy beachfront condos to spacious homes with ample room for families or groups. Many rentals include fully equipped kitchens, allowing for convenient meal preparation, as well as outdoor spaces such as patios or balconies where guests can relax and enjoy the beautiful Florida weather.

The area itself offers a vibrant lifestyle with access to local attractions, beautiful beaches, and recreational activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a South Island vacation rental?
Book your South Island vacation 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 vacation 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 range of attractions that highlight the area's natural beauty and recreational opportunities. The nearby beaches, particularly those on Sanibel Island, are renowned for their pristine sands and excellent shelling, making them a popular destination for nature enthusiasts. The J.N. "Ding" Darling National Wildlife Refuge on Sanibel Island offers opportunities for bird watching, kayaking, and exploring the unique ecosystems of the region.

For those interested in history and culture, the Bailey-Matthews National Shell Museum provides insights into the local marine environment and the art of shell collecting. Additionally, the charming downtown area of Captiva Island features boutique shops, art galleries, and restaurants, making it a lovely spot to explore.

Outdoor activities abound, with options for fishing, boating, and biking along the scenic trails.
Can I change or cancel my South Island home rental booking on Vrbo?
To find South Island vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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