South Island holiday rentals

We found 1,168 holiday rentals — enter your dates for availability
Select from 41 houses, 202 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:13 Nov - 20 Nov

Private kitchen
Property grounds
Private kitchen
Room
Exceptional
(9 reviews)

Luxury Modern Beachside House with Heated Pool & Elevator in Fort Myers Beach

Fort Myers Beach

8% off
S$8,449
for 7 nights, 1 home
S$1,207 per night
includes taxes & fees
Luxury Modern Beachside House with Heated Pool & Elevator in Fort Myers Beach
Outdoor dining
Living area
Room
Private kitchen
Exceptional
(7 reviews)

Sun Kiss Villas - Beachside Duplex, Private Pool and Steps to Beach

Fort Myers Beach

8% off
S$8,753
for 7 nights, 1 home
S$1,250 per night
includes taxes & fees
Sun Kiss Villas - Beachside Duplex, Private Pool and Steps to Beach
Living area
Pool
Interior
Living area
Exceptional
(5 reviews)

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

Fort Myers Beach

8% off
S$10,486
for 7 nights, 1 home
S$1,498 per night
includes taxes & fees
Spacious 5-bedroom house w/ Elevator, Canal, and heated pool Fort Myers Beach
Terrace/patio
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
S$6,464
for 7 nights, 1 home
S$923 per night
includes taxes & fees
🐾 Pet Friendly, Heated Pool, Gorgeous Renovation, Walk to the sugar sand of FMB!
Outside Shower and Back Steps Entrance
Sun Room
Living area
Dining Area
Exceptional
(85 reviews)

Elevator to Paradise: Luxury Beachfront Escape with Incredible Ocean Views!

Fort Myers Beach

7% off
S$7,355
for 7 nights, 1 home
S$1,051 per night
includes taxes & fees
Elevator to Paradise: Luxury Beachfront Escape with Incredible Ocean Views!
Pool
Living area
Exterior
Living area
Exceptional
(19 reviews)

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

Fort Myers Beach

7% off
S$3,730
for 7 nights, 1 home
S$533 per night
includes taxes & fees
Oceanview 3-bdrm home steps from beach! Heated pool & hot tub. Sleeps 6.
Living area
Terrace/patio
Interior
Interior
Exceptional
(15 reviews)

Gulf access and surrounded by water

Fort Myers Beach

8% off
S$5,984
for 7 nights, 1 home
S$855 per night
includes taxes & fees
Gulf access and surrounded by water
Private kitchen
Living area
Room
Private kitchen
Exceptional
(14 reviews)

Sandy Feet Retreat - 3Bdrms, Pool, Steps to Beach

Fort Myers Beach

7% off
S$4,150
for 7 nights, 1 home
S$593 per night
includes taxes & fees
Sandy Feet Retreat - 3Bdrms, Pool, Steps to Beach
Open floor plan with eat in bar
Exterior
Comfy seating with sleeper sofa
Foosball anyone?
Exceptional
(20 reviews)

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

Fort Myers Beach

7% off
S$4,549
for 7 nights, 1 apartment
S$650 per night
includes taxes & fees
🐾 Dog Friendly, Large Heated Pool, Short Walk to the sugar sand Beach!
Outdoor dining
Private kitchen
Living area
Exterior
Exceptional
(13 reviews)

Cozy Coastal Retreat, Steps to the Sugar Sand Beach of FMB!

Fort Myers Beach

7% off
S$2,314
for 7 nights, 1 home
S$331 per night
includes taxes & fees
Cozy Coastal Retreat, Steps to the Sugar Sand Beach of FMB!
Living area
Aerial photo of our beach.
Pool
Kitchen with new table and chairs. New ceiling fan with remote.
Exceptional
(75 reviews)

Clean & Comfortable Beachfront Condo. New restaurants right across the street!

Fort Myers Beach

7% off
S$2,113
for 7 nights, 1 apartment
S$302 per night
includes taxes & fees
Clean & Comfortable Beachfront Condo. New restaurants right across the street!
Interior
Property grounds
Pool
Room
Exceptional
(61 reviews)

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

Fort Myers Beach

7% off
S$2,249
for 7 nights, 1 apartment
S$321 per night
includes taxes & fees
Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet
Living area
Property grounds
Exterior
Private kitchen
Exceptional
(7 reviews)

Not available due to hurricane Ian damage

Fort Myers Beach

8% off
S$3,112
for 7 nights, 1 apartment
S$445 per night
includes taxes & fees
Not available due to hurricane Ian damage
Room
Interior
Beach
Private kitchen
Exceptional
(9 reviews)

Booking for winter 2025-2026.

Fort Myers Beach

8% off
S$2,172
for 7 nights, 1 apartment
S$310 per night
includes taxes & fees
Booking for winter 2025-2026.
Living area
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$2,696
for 7 nights, 1 apartment
S$385 per night
includes taxes & fees
Gorgeous Beach Front Condo with Amazing Gulf and Beach Views, Master Ensuite too!
Kitchen
Room
Master bedroom
Lake view from lanai
Exceptional
(11 reviews)

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

Fort Myers Beach

7% off
S$3,713
for 7 nights, 1 apartment
S$530 per night
includes taxes & fees
Bella Vie on Ft Myers Beach with 4 min walk to beach, lanai, pool, & gym
Birdseye view from water
Sports court
Cozy Kitchen
Pool
Exceptional
(22 reviews)

Veteran Owned Beachfront, Sleeps 4.

Fort Myers Beach

7% off
S$1,866
for 7 nights, 1 apartment
S$267 per night
includes taxes & fees
Veteran Owned Beachfront, Sleeps 4.
Exterior detail
Living area
Living area
Pool
Exceptional
(6 reviews)

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

Fort Myers Beach

7% off
S$4,029
for 7 nights, 1 home
S$576 per night
includes taxes & fees
Flip Flop Paradise - 3 Bdrms, Pool, Steps to the Beach
Exterior
Interior
Living area
Pool
Exceptional
(72 reviews)

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

Fort Myers Beach

7% off
S$2,210
for 7 nights, 1 apartment
S$316 per night
includes taxes & fees
Beach front with 2 bedrooms, 2 baths and views of the Gulf!
Bathroom
Pool
Room
Living area
Exceptional
(5 reviews)

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

Fort Myers Beach

7% off
S$2,616
for 7 nights, 1 apartment
S$374 per night
includes taxes & fees
Bright 2BR/2BA • Walk to Beach & Shopping • Canal View • Large Pool & Beach Gear
View to the living area
Exterior
Beach
Cozy seating for watching TV or an afternoon nap
Excellent
(14 reviews)

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

Fort Myers Beach

7% off
S$3,037
for 7 nights, 1 apartment
S$434 per night
includes taxes & fees
🐾 Pet Friendly, Heated Pool, Gorgeous Renovation, Walk to the sugar sand of FMB!
Living room
Ariel shot of the Bac Bay at the northern end of the island.
Living Room
Living Room
Exceptional
(51 reviews)

Sleeps 8 - Perfect condo for the Family!

Fort Myers Beach

8% off
S$2,441
for 7 nights, 1 apartment
S$349 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.

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