Family-Friendly Vacation Rentals in South Island, FL: Compare 10+ Sites & Save

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  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  Florida
  5.  Fort Myers
  6.  South Island

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916 Best Family Vacation Rentals in South Island (Starting from $138)

Royal Pelican 173
Royal Pelican 173
Apartment
Fort Myers Beach, FL, USA
0.1k from South Island center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms6 Guests
New to Booking
$403
Average price / night
Check Availability
Water views, beaches, restaurants! STR  R260158
Water views, beaches, restaurants! STR R260158
Condo
Fort Myers Beach, FL, 33931, United States
0.2k from South Island center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

23 reviews

$139
Average price / night
Check Availability
Royal Pelican - New Listing - 4511 Bay Beach Ln condo
Royal Pelican - New Listing - 4511 Bay Beach Ln condo
Apartment
Fort Myers Beach, FL, USA
0.1k from South Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals, Condos

2 Bedrooms6 Guests
New to Booking
$177
Average price / night
Check Availability
Spacious 2 Bedroom Condo Minutes 5 minutes from Ocean!
Spacious 2 Bedroom Condo Minutes 5 minutes from Ocean!
Condo
Fort Myers Beach, FL, 33931, United States
0.2k from South Island center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms5 Guests
New to Booking
$409
Average price / night
Check Availability
Casa Marina 224
Casa Marina 224
Apartment
Fort Myers Beach, FL, USA
0.2k from South Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Family, Beach rentals

2 Bedrooms4 Guests
9.0

Fabulous

1 reviews

$181
Average price / night
Check Availability
Welcome to Paradise in the Penthouse
Welcome to Paradise in the Penthouse
Condo
Fort Myers Beach, FL, 33931, United States
0.3k from South Island center

AC, Balcony, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

38 reviews

$274
Average price / night
Check Availability
Hibiscus 844
Hibiscus 844
Apartment
Fort Myers Beach, FL, USA
0.2k from South Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay

2 Bedrooms6 Guests
New to Booking
$392
Average price / night
Check Availability
Beautiful Water view Condo on Ft. Meyers Beach!! Survived Ian!
Beautiful Water view Condo on Ft. Meyers Beach!! Survived Ian!
Condo
Fort Myers Beach, FL, 33931, United States
0.3k from South Island center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Heater, Hot Tub

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$182
Average price / night
Check Availability
Casa Marina III -644 by Sun Palace
Casa Marina III -644 by Sun Palace
House
Fort Myers Beach, FL, USA
0.2k from South Island center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$207
Average price / night
Check Availability
Beautiful Condo, at Bella Lago. Steps to the beach! Resort Amenities\n
Beautiful Condo, at Bella Lago. Steps to the beach! Resort Amenities\n
Condo
Fort Myers Beach, FL, 33931, United States
0.4k from South Island center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$332
Average price / night
Check Availability
Hibiscus Pointe 342, Canal View, 2 Bedroom, Sleeps 6, Heated Pool, Elevator
Hibiscus Pointe 342, Canal View, 2 Bedroom, Sleeps 6, Heated Pool, Elevator
Apartment
South Island, Fort Myers Beach, Florida, USA
0.2k from South Island center

Kitchen, Air Conditioner, Parking, Pool, Hot Tub, Internet, Wheelchair Accessible

2 Bedrooms6 Guests
New to Booking
$154
Average price / night
Check Availability
Vaulted Penthouse Loft with view Gulf Mexico on Intercoastal Waterway.Large pool
Vaulted Penthouse Loft with view Gulf Mexico on Intercoastal Waterway.Large pool
Condo
Fort Myers Beach, FL, 33931, United States
0.4k from South Island center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms5 Guests
9.4

Superb

60 reviews

$348
Average price / night
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Luxury Beach Condo Located On The Bay In A Tropical Oasis!
Luxury Beach Condo Located On The Bay In A Tropical Oasis!
House
South Island, Fort Myers Beach, Florida, USA
0.2k from South Island center

Luxury, Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings

1 Bedroom4 Guests
9.8

Exceptional

8 reviews

$138
Average price / night
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NEW LUXURY 3 Bedroom Condo Steps From Private Beach with Pool
NEW LUXURY 3 Bedroom Condo Steps From Private Beach with Pool
Condo
Fort Myers Beach, FL, 33931, United States
0.4k from South Island center

AC, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

14 reviews

$460
Average price / night
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Casa Marina 654 - 4321 Bay Beach Lane condo
Casa Marina 654 - 4321 Bay Beach Lane condo
Apartment
Fort Myers Beach, FL, USA
0.2k from South Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals, Condos

2 Bedrooms6 Guests
New to Booking
$176
Average price / night
Check Availability
Directly on the beach at The Estero Beach and Tennis club. Balcony on the Ocean!
Directly on the beach at The Estero Beach and Tennis club. Balcony on the Ocean!
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.8

Exceptional

142 reviews

$245
Average price / night
Check Availability
Santa Maria 104
Santa Maria 104
Apartment
Fort Myers Beach, FL, USA
0.2k from South Island center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Hot tubs, Places to stay, Family

2 Bedrooms4 Guests
New to Booking
$194
Average price / night
Check Availability
Sandy, white beaches right outside your door! Relax and let the good times roll!
Sandy, white beaches right outside your door! Relax and let the good times roll!
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Laundry, Living Area

2 Bedrooms8 Guests
New to Booking
$342
Average price / night
Check Availability
Santa Maria 108
Santa Maria 108
Apartment
Fort Myers Beach, FL, USA
0.3k from South Island center

Apartments, Accommodations, Parking, Lodgings, Jacuzzis, Places to stay

2 Bedrooms6 Guests
New to Booking
$347
Average price / night
Check Availability
Stunning 1-bedroom condo on enjoyable Fort Myers Beach with AC
Stunning 1-bedroom condo on enjoyable Fort Myers Beach with AC
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

1 Bedroom4 Guests
New to Booking
$187
Average price / night
Check Availability
Estero Beach & Tennis Club 706B | Modern Beach Front Condo
Estero Beach & Tennis Club 706B | Modern Beach Front Condo
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Elevator, Free Parking, Heater, Kitchen, Living Area, Microwave

2 Bedrooms4 Guests
8.8

Fabulous

3 reviews

$191
Average price / night
Check Availability
11th Floor Beachfront GULFBEACHSUNSET VIEWS!  Lic #19-0340 STRAP # 034724W10370B
11th Floor Beachfront GULFBEACHSUNSET VIEWS! Lic #19-0340 STRAP # 034724W10370B
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.8

Exceptional

45 reviews

$256
Average price / night
Check Availability
GULF OF AMERICA & ESTERO BAY VIEWS from this 8th floor penthouse, MUST SEE
GULF OF AMERICA & ESTERO BAY VIEWS from this 8th floor penthouse, MUST SEE
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
10.0

Exceptional

35 reviews

$806
Average price / night
Check Availability
Fort Myers Beach condo direct Gulf View #PH5B - Pool, WIFI, Tennis, Pickleball
Fort Myers Beach condo direct Gulf View #PH5B - Pool, WIFI, Tennis, Pickleball
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

49 reviews

$249
Average price / night
Check Availability
Penthouse gulf view on the beach
Penthouse gulf view on the beach
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

1 Bedroom4 Guests
9.4

Superb

66 reviews

$260
Average price / night
Check Availability
Fort Myers Beach Condo on the Gulf
Fort Myers Beach Condo on the Gulf
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Free Parking, Heater, Internet

1 Bedroom4 Guests
9.8

Exceptional

34 reviews

$239
Average price / night
Check Availability
Spacious Gulf Front Condo- Steps to Beach, Tennis  + Pool
Spacious Gulf Front Condo- Steps to Beach, Tennis + Pool
Condo
Fort Myers Beach, FL, 33931, United States
0.5k from South Island center

AC, Balcony, Barbecue, Elevator, Extra Bed, Heater, Kitchen, Living Area, Microwave

1 Bedroom4 Guests
7.6

Good

27 reviews

$194
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Family Vacation Rentals in South Island.

Stay Near South Island's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

South Island Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 916 verified family-friendly vacation rentals in South Island. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in South Island vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $138 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in South Island offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in South Island are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in South Island often include amenities such as Pool, Child Friendly, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.