South Island holiday rentals

We found 1,176 holiday rentals — enter your dates for availability
Select from 43 houses, 207 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:27 Nov - 4 Dec

Living area
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
S$10,409
for 7 nights, 1 home
S$1,487 per night
includes taxes & fees
Spacious 5-bedroom house w/ Elevator, Canal, and heated pool Fort Myers Beach
Pool
Living area
Living area
Private kitchen
Exceptional
(20 reviews)

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

Fort Myers Beach

6% off
S$4,766
for 7 nights, 1 home
S$681 per night
includes taxes & fees
Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 6.
Private kitchen
Living area
Exterior
Room
Wonderful
(35 reviews)

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

Fort Myers Beach

7% off
S$3,290
for 7 nights, 1 apartment
S$470 per night
includes taxes & fees
Gorgeous Beach Front Condo with Amazing Gulf and Beach Views, Master Ensuite too!
Pool
Terrace/patio
Interior
Living area
Exceptional
(15 reviews)

Gulf access and surrounded by water

Fort Myers Beach

8% off
S$6,780
for 7 nights, 1 home
S$969 per night
includes taxes & fees
Gulf access and surrounded by water
Pool
Property grounds
Interior
Room
Exceptional
(61 reviews)

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

Fort Myers Beach

7% off
S$2,293
for 7 nights, 1 apartment
S$328 per night
includes taxes & fees
Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet
Pool
Interior
Living area
Living area
Exceptional
(72 reviews)

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

Fort Myers Beach

8% off
S$2,277
for 7 nights, 1 apartment
S$325 per night
includes taxes & fees
Beach front with 2 bedrooms, 2 baths and views of the Gulf!
Living area
Interior
Private kitchen
Room
Exceptional
(9 reviews)

Booking for winter 2025-2026.

Fort Myers Beach

8% off
S$2,156
for 7 nights, 1 apartment
S$308 per night
includes taxes & fees
Booking for winter 2025-2026.
Pool
Living area
Private kitchen
Dining
Wonderful
(7 reviews)

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

Fort Myers Beach

7% off
S$3,492
for 7 nights, 1 apartment
S$499 per night
includes taxes & fees
Gorgeous Beach Front Condo with Amazing Gulf and Beach Views, Master Ensuite too!
Master bedroom
Room
Lake view from lanai
Interior
Exceptional
(11 reviews)

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

Fort Myers Beach

7% off
S$6,096
for 7 nights, 1 apartment
S$871 per night
includes taxes & fees
Bella Vie on Ft Myers Beach with 4 min walk to beach, lanai, pool, & gym
Exterior
Property grounds
Private kitchen
Living area
Exceptional
(7 reviews)

Not available due to hurricane Ian damage

Fort Myers Beach

8% off
S$3,089
for 7 nights, 1 apartment
S$441 per night
includes taxes & fees
Not available due to hurricane Ian damage
Living Room
Ariel shot of the Bac Bay at the northern end of the island.
View of the building
Living Room
Exceptional
(51 reviews)

Sleeps 8 - Perfect condo for the Family!

Fort Myers Beach

8% off
S$2,418
for 7 nights, 1 apartment
S$345 per night
includes taxes & fees
Sleeps 8 - Perfect condo for the Family!

  • 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

What is the most popular type of holiday rental accommodation in South Island?
The most in-demand types of holiday rentals in South Island are condos. Want something different? Vrbo has a variety of options to match the diverse needs of our guests, so you'll see holiday homes in loads of sizes and shapes. The ideal home away from home is waiting for you — discover yours today.
How much does it cost to rent a holiday rental in South Island?
The average price for a holiday home in South Island is based on several factors, like time of year, length of stay and property type. Whether you prefer a sprawling house with room for friends and family or a comfy cabin for you and your other half, just add your travel dates to see stays with unbeatable value.
How much does it cost to rent a beach house in South Island?
Prices for beach houses in South Island may vary depending on the style and size of the property and when you plan to travel. Simply enter your travel dates into Vrbo and how many guests to see your rental options and prices. From there you can use the filters to narrow down your search by ratings, nearby activities, amenities and more.
What are popular rental amenities in South Island?
When it comes to rental amenities that people prefer in South Island, nearby museums, a barbecue grill and a fireplace are the most popular. With Vrbo holiday rentals, you'll find options to fit your taste and style, whether you're going on a holiday with your partner, your family or even pets.
Can I find two-bedroom holiday rentals in South Island?
South Island has 285 two-bedroom holiday rentals for you to select from. Experience a holiday home with all the comfort and privacy you want at a fantastic price on Vrbo.
Are there holiday rentals with WiFi in South Island?
You can pick from 259 holiday rentals with WiFi in South Island. If you want to disconnect from the world on your trip, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a holiday rental in South Island?
The minimum age is usually 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your preferred South Island holiday rental before booking your trip.
How long can I rent a holiday rental in South Island for?
The amount of time you can stay in a South Island holiday home for is up to each property. Simply enter your preferred travel dates to view options offering extended stays. They feature all you need to make your extended break more comfortable such as kitchens and yards. Some Vrbo holiday properties may also offer discounted weekly or monthly prices, so you can stay even longer for less.

More holiday ideas