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

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338 Best Family Vacation Rentals in Ole (Starting from $107)

Shady Palm Villa
Shady Palm Villa
Apartment
Lely Resort, FL, USA
0.1k from Ole center

Apartments, Accommodations, Pools, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
New to Booking
$295
Average price / night
Check Availability
Santa Ana Retreat: Naples, Florida
Santa Ana Retreat: Naples, Florida
House
Naples, FL, 34113, United States
0.2k from Ole center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$177
Average price / night
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Yuba Oasis
Yuba Oasis
Apartment
Lely Resort, FL, USA
0.3k from Ole center

Apartments, Accommodations, Pools, Lodgings, Places to stay, Accessible hotels

2 Bedrooms4 Guests
New to Booking
$194
Average price / night
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NAPLES, FLORIDA, Lely, OLE'  Community
NAPLES, FLORIDA, Lely, OLE' Community
House
Naples, FL, 34113, United States
0.3k from Ole center

AC, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$270
Average price / night
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Flamingo Fairways II
Flamingo Fairways II
House
Lely Resort, FL, USA
0.3k from Ole center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom6 Guests
New to Booking
$327
Average price / night
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Naples Snowbird Escape w/ Pool! 7 Mi to Beach
Naples Snowbird Escape w/ Pool! 7 Mi to Beach
House
Naples, FL, 34113, United States
0.4k from Ole center

AC, Fitness Equipment, Free Parking, Heater, Kitchen, Microwave, No Smoking, Outdoor Space, Patio

2 Bedrooms4 Guests
New to Booking
$131
Average price / night
Check Availability
Lely Resort Condo about 10 Mi to Naples Beach!
Lely Resort Condo about 10 Mi to Naples Beach!
Apartment
Lely Resort, FL, USA
0.4k from Ole center

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

3 Bedrooms6 Guests
New to Booking
$216
Average price / night
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Luxury Townhouse with resort style amenities in OLE, Naples
Luxury Townhouse with resort style amenities in OLE, Naples
House
Naples, FL, 34113, United States
0.5k from Ole center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$250
Average price / night
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Alluring Naples Retreat with Resort Amenities!
Alluring Naples Retreat with Resort Amenities!
House
Naples, FL, USA
0.5k from Ole center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Hot tubs

3 Bedrooms10 Guests
New to Booking
$188
Average price / night
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Alluring Naples Retreat w/ Resort Amenities!
Alluring Naples Retreat w/ Resort Amenities!
House
Naples, FL, 34113, United States
0.5k from Ole center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms10 Guests
6.0

Review score

1 reviews

$158
Average price / night
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Naples Resort Townhome with Endless Amenities!
Naples Resort Townhome with Endless Amenities!
House
Lely Resort, FL, USA
0.6k from Ole center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

3 Bedrooms6 Guests
New to Booking
$347
Average price / night
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Enjoy This Tropical Getaway with a Full Service Village in Southern Naples!
Enjoy This Tropical Getaway with a Full Service Village in Southern Naples!
Condo
Naples, FL, 34113, United States
0.6k from Ole center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$219
Average price / night
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Ole at Lely Resort Condo with Pool Access!
Ole at Lely Resort Condo with Pool Access!
Apartment
Lely Resort, FL, USA
0.7k from Ole center

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

3 Bedrooms8 Guests
New to Booking
$394
Average price / night
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Sunny Get Away in  Ole at Lely, Naples in Cozy Townhouse.
Sunny Get Away in Ole at Lely, Naples in Cozy Townhouse.
Condo
Naples, FL, 34113, United States
0.6k from Ole center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

9 reviews

$107
Average price / night
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Naples Condo 10 Mi to Beach Pool and Hot Tub Access
Naples Condo 10 Mi to Beach Pool and Hot Tub Access
Apartment
Naples, FL, USA
0.8k from Ole center

Apartments, Accommodations, Parking, Spa, Lodgings, Hot tubs, Places to stay, Condos

2 Bedrooms4 Guests
New to Booking
$236
Average price / night
Check Availability
Ole' Lely Resort-Lots of amenities!-close to Marco Island & 5th Ave!
Ole' Lely Resort-Lots of amenities!-close to Marco Island & 5th Ave!
House
Naples, FL, 34113, United States
0.7k from Ole center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$232
Average price / night
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Coral Falls- Celeste Dr./Lely
Coral Falls- Celeste Dr./Lely
House
Belle Meade, FL, USA
0.8k from Ole center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

1 Bedroom4 Guests
New to Booking
$233
Average price / night
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Tropical Paradise in Lely Ole'
Tropical Paradise in Lely Ole'
House
Naples, FL, 34113, United States
0.7k from Ole center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$337
Average price / night
Check Availability
Quiet Lely Resort Condo with Pool - 2 Mi to Golf!
Quiet Lely Resort Condo with Pool - 2 Mi to Golf!
Apartment
Naples, FL, USA
0.8k from Ole center

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

2 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$141
Average price / night
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Ole at Lely Resort Condo w/ Pool Access!
Ole at Lely Resort Condo w/ Pool Access!
Condo
Naples, FL, 34113, United States
0.7k from Ole center

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

3 Bedrooms8 Guests
8.0

Good

1 reviews

$426
Average price / night
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Luxe Top-Floor Condo in Beautiful Lely Resort
Luxe Top-Floor Condo in Beautiful Lely Resort
Apartment
Old Marco Junction, FL, USA
0.8k from Ole center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$158
Average price / night
Check Availability
Naples Condo 10 Mi to Beach: Pool & Hot Tub Access
Naples Condo 10 Mi to Beach: Pool & Hot Tub Access
Condo
Naples, FL, 34113, United States
0.8k from Ole center

AC, Balcony, Barbecue, Elevator, Free Parking, Heater, Hot Tub, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$185
Average price / night
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Quiet Lely Resort Condo w/ Pool - 2 Mi to Golf!
Quiet Lely Resort Condo w/ Pool - 2 Mi to Golf!
Condo
Naples, FL, 34113-3091, United States
0.8k from Ole center

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

2 Bedrooms6 Guests
9.6

Exceptional

19 reviews

$160
Average price / night
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Newly Furnished Top-Floor 2 Bed/2 Bath Condo in Lely Resort!
Newly Furnished Top-Floor 2 Bed/2 Bath Condo in Lely Resort!
Condo
Naples, FL, 34113, United States
0.8k from Ole center

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

2 Bedrooms4 Guests
9.6

Exceptional

19 reviews

$165
Average price / night
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NEW LISTING! 3BR/2BA Golf Course/Pool Home in Lely Resort w PLAYERS CLUB access
NEW LISTING! 3BR/2BA Golf Course/Pool Home in Lely Resort w PLAYERS CLUB access
House
Naples, FL, 34113, United States
0.9k from Ole center

AC, Barbecue, Dryer, Heater, Internet, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$393
Average price / night
Check Availability
Luxury home, new saltwater pool, completely remodeled with private casita.
Luxury home, new saltwater pool, completely remodeled with private casita.
House
Naples, FL, 34113, United States
0.9k from Ole center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$586
Average price / night
Check Availability
NEW Luxury 2 BR plus den in Greenlinks Condo totally remodeled!
NEW Luxury 2 BR plus den in Greenlinks Condo totally remodeled!
Condo
Naples, FL, 34113, United States
1.0k from Ole center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$216
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 Ole.

Stay Near Ole's Top Attractions

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

Ole Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 338 verified family-friendly vacation rentals in Ole. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Ole vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $107 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Ole 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 Ole 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 Ole often include amenities such as Child Friendly, Wellness Facilities, and Fireplace/Heating. 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.