South Island holiday rentals

We found 1,172 holiday rentals — enter your dates for availability
Select from 45 houses, 213 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:11 Dec - 18 Dec

Living area
Interior
Living area
Private kitchen
Exceptional
(40 reviews)

🐾 Pet Friendly, Heated Pool, Gorgeous Renovation, Walk to the sugar sand of FMB!

Fort Myers Beach

7% off
AU$8,884
for 7 nights, 1 home
AU$1,269 per night
includes taxes & fees
🐾 Pet Friendly, Heated Pool, Gorgeous Renovation, Walk to the sugar sand of FMB!
Exterior
Pool
Living area
Interior
Exceptional
(5 reviews)

Spacious 5-bedroom house w/ Elevator, Canal, and heated pool Fort Myers Beach

Fort Myers Beach

8% off
AU$11,299
for 7 nights, 1 home
AU$1,614 per night
includes taxes & fees
Spacious 5-bedroom house w/ Elevator, Canal, and heated pool Fort Myers Beach
Private kitchen
Private kitchen
Interior
Property grounds
Exceptional
(13 reviews)

Sleeps 16--New Pool!--7 min walk to beach, Bay views!

Fort Myers Beach

8% off
AU$9,280
for 7 nights, 1 home
AU$1,326 per night
includes taxes & fees
Sleeps 16--New Pool!--7 min walk to beach, Bay views!
Private kitchen
Property grounds
Pool
Room
Exceptional
(61 reviews)

Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet

Fort Myers Beach

8% off
AU$2,860
for 7 nights, 1 apartment
AU$409 per night
includes taxes & fees
Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet
Private kitchen
Living area
Exterior
Property grounds
Wonderful
(35 reviews)

Gorgeous Beach Front Condo with Amazing Gulf and Beach Views, Master Ensuite too!

Fort Myers Beach

7% off
AU$3,969
for 7 nights, 1 apartment
AU$567 per night
includes taxes & fees
Gorgeous Beach Front Condo with Amazing Gulf and Beach Views, Master Ensuite too!
Pool
Living area
Private kitchen
Living area
Wonderful
(7 reviews)

Gorgeous Beach Front Condo with Amazing Gulf and Beach Views, Master Ensuite too!

Fort Myers Beach

7% off
AU$4,153
for 7 nights, 1 apartment
AU$593 per night
includes taxes & fees
Gorgeous Beach Front Condo with Amazing Gulf and Beach Views, Master Ensuite too!
Pool
Living area
Living area
Exterior
Exceptional
(20 reviews)

Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 6.

Fort Myers Beach

8% off
AU$4,474
for 7 nights, 1 home
AU$639 per night
includes taxes & fees
Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 6.
Room
Interior
Private kitchen
Living area
Exceptional
(9 reviews)

Booking for winter 2025-2026.

Fort Myers Beach

8% off
AU$2,380
for 7 nights, 1 apartment
AU$340 per night
includes taxes & fees
Booking for winter 2025-2026.
Open floor plan with eat in bar
Exterior
Foosball anyone?
Beach
Exceptional
(20 reviews)

🐾 Dog Friendly, Large Heated Pool, Short Walk to the sugar sand Beach!

Fort Myers Beach

7% off
AU$6,167
for 7 nights, 1 apartment
AU$881 per night
includes taxes & fees
🐾 Dog Friendly, Large Heated Pool, Short Walk to the sugar sand Beach!
Bathroom
Pool
Living area
Property grounds
Exceptional
(5 reviews)

Bright 2BR/2BA • Walk to Beach & Shopping • Canal View • Large Pool & Beach Gear

Fort Myers Beach

7% off
AU$3,164
for 7 nights, 1 apartment
AU$452 per night
includes taxes & fees
Bright 2BR/2BA • Walk to Beach & Shopping • Canal View • Large Pool & Beach Gear
Exterior
Interior
Living area
Pool
Exceptional
(72 reviews)

Beach front with 2 bedrooms, 2 baths and views of the Gulf!

Fort Myers Beach

8% off
AU$2,603
for 7 nights, 1 apartment
AU$372 per night
includes taxes & fees
Beach front with 2 bedrooms, 2 baths and views of the Gulf!
Exterior
Property grounds
Beach
Private kitchen
Exceptional
(7 reviews)

Not available due to hurricane Ian damage

Fort Myers Beach

8% off
AU$3,343
for 7 nights, 1 apartment
AU$478 per night
includes taxes & fees
Not available due to hurricane Ian damage
Kitchen
Room
Lake view from lanai
Master bedroom
Exceptional
(11 reviews)

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

Fort Myers Beach

8% off
AU$6,522
for 7 nights, 1 apartment
AU$932 per night
includes taxes & fees
Bella Vie on Ft Myers Beach with 4 min walk to beach, lanai, pool, & gym
Living Room
Ariel shot of the Bac Bay at the northern end of the island.
Living room
View of the building
Exceptional
(51 reviews)

Sleeps 8 - Perfect condo for the Family!

Fort Myers Beach

7% off
AU$2,697
for 7 nights, 1 apartment
AU$385 per night
includes taxes & fees
Sleeps 8 - Perfect condo for the Family!
Cozy seating for watching TV or an afternoon nap
Exterior
Private kitchen
View to the living area
Excellent
(14 reviews)

🐾 Pet Friendly, Heated Pool, Gorgeous Renovation, Walk to the sugar sand of FMB!

Fort Myers Beach

7% off
AU$3,962
for 7 nights, 1 apartment
AU$566 per night
includes taxes & fees
🐾 Pet Friendly, Heated Pool, Gorgeous Renovation, Walk to the sugar sand of FMB!
  • 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, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

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.
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.
Are all fees included in the South Island holiday homes prices shown on Stayz?
Stayz 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.
Are there any South Island holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for South Island holiday homes?
You can find great discounts on holiday homes in South Island on Stayz, 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.
Can I change or cancel my South Island holiday home booking on Stayz?
To find South Island holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in South Island?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a South Island holiday home?
Book your South Island holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in South Island?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in South Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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