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

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  2. Family Vacation Rentals
  3.  USA

  4.  Florida
  5.  St. Petersburg - Clearwater
  6.  Diamond Isle

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1191 Best Family Vacation Rentals in Diamond Isle (Starting from $147)

Clearwater Beach Oasis Retreat - Entire Resort
Clearwater Beach Oasis Retreat - Entire Resort
House
Clearwater Beach, FL, USA
0.4k from Diamond Isle center

Air Conditioner, Parking, Security/Safety, Pool, Internet, Child Friendly

10 Bedrooms30 Guests
New to Booking
$2331
Average price / night
Check Availability
ORANGE BLOSSOM COTTAGE two minute Walk to Beach
ORANGE BLOSSOM COTTAGE two minute Walk to Beach
Cottage
Clearwater, FL, 33767, United States
0.1k from Diamond Isle center

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

2 Bedrooms6 Guests
9.6

Exceptional

85 reviews

$340
Average price / night
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Coconut Grove Resort Oasis
Coconut Grove Resort Oasis
House
Clearwater Beach, FL, USA
0.4k from Diamond Isle center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

10 Bedrooms30 Guests
New to Booking
$3300
Average price / night
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Coastal Waterside Condo 2 Blocks to Beach
Coastal Waterside Condo 2 Blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Microwave

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$312
Average price / night
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By the Beach Rentals
By the Beach Rentals
Apartment
Clearwater Beach, FL, USA
0.4k from Diamond Isle center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Self-catering

20 Bedrooms40 Guests
8.9

Fabulous

119 reviews

$1034
Average price / night
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Waterfront Coastal Condo 2 Blocks to Beach
Waterfront Coastal Condo 2 Blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom4 Guests
New to Booking
$299
Average price / night
Check Availability
Five Palms Suite 103 - Daily - Weekly - Monthly
Five Palms Suite 103 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom4 Guests
1.0

Review score

1 reviews

$155
Average price / night
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Waterfront Bungalow Oasis 2 Blocks to Beach
Waterfront Bungalow Oasis 2 Blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking, Outdoor Space

1 Bedroom4 Guests
10.0

Exceptional

3 reviews

$294
Average price / night
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Five Palms Suite 104 - Daily - Weekly - Monthly
Five Palms Suite 104 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom4 Guests
New to Booking
$154
Average price / night
Check Availability
Coastal Waterfront Condo 2 blocks to Beach
Coastal Waterfront Condo 2 blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$295
Average price / night
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Five Palms Suite 105 - Daily - Weekly - Monthly
Five Palms Suite 105 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

2 Bedrooms9 Guests
New to Booking
$357
Average price / night
Check Availability
Beachy Bayfront Condo Walk to Beach
Beachy Bayfront Condo Walk to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking, TV

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$316
Average price / night
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Five Palms Suite 106 - Daily - Weekly - Monthly
Five Palms Suite 106 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom6 Guests
10.0

Exceptional

1 reviews

$163
Average price / night
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Waterfront Courtyard Condo 2 Blocks to Beach
Waterfront Courtyard Condo 2 Blocks to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Balcony, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$325
Average price / night
Check Availability
Five Palms Vacation Rentals- Daily - Weekly - Monthly
Five Palms Vacation Rentals- Daily - Weekly - Monthly
Apartment
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Oceanfront, Air Conditioner, View, Balcony/Terrace, Laundry, Fireplace/Heating, Guest Services

20 Bedrooms87 Guests
8.9

Fabulous

10 reviews

$736
Average price / night
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Direct Waterfront `The Lily Pad` Walk to Beach
Direct Waterfront `The Lily Pad` Walk to Beach
Apartment
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Microwave, No Smoking, Outdoor Space

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$342
Average price / night
Check Availability
Five Palms Suite 108 - Daily - Weekly - Monthly
Five Palms Suite 108 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom4 Guests
New to Booking
$166
Average price / night
Check Availability
New-Endless Amenities-Unmatched Rooftop & Views
New-Endless Amenities-Unmatched Rooftop & Views
House
Clearwater, FL, 33767, United States
0.4k from Diamond Isle center

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

7 Bedrooms19 Guests
10.0

Exceptional

3 reviews

$2398
Average price / night
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Five Palms Suite 109 - Daily - Weekly - Monthly
Five Palms Suite 109 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Pool, Laundry, Kitchen, Air Conditioner, Balcony/Terrace, Wheelchair Accessible, Parking

1 Bedroom4 Guests
New to Booking
$147
Average price / night
Check Availability
Lovely renovated condo with water views, great value for outstanding amenities
Lovely renovated condo with water views, great value for outstanding amenities
Condo
Clearwater Beach, FL, 33767, United States
0.4k from Diamond Isle center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$175
Average price / night
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Five Palms Suite 110 - Daily - Weekly - Monthly
Five Palms Suite 110 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom4 Guests
9.0

Fabulous

1 reviews

$163
Average price / night
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Luxurious King Bed! Steps to beach, town & park!
Luxurious King Bed! Steps to beach, town & park!
Apartment
Clearwater, FL, 33767, United States
0.5k from Diamond Isle center

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

9.8

Exceptional

103 reviews

$492
Average price / night
Check Availability
Five Palms Suite 202 - Daily - Weekly - Monthly
Five Palms Suite 202 - Daily - Weekly - Monthly
House
Diamond Isle, Clearwater Beach, Florida, USA
0.4k from Diamond Isle center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Wheelchair Accessible, Laundry

1 Bedroom4 Guests
New to Booking
$236
Average price / night
Check Availability
New-Waterslide-Spa-Rooftop-Gulf & Bay Views
New-Waterslide-Spa-Rooftop-Gulf & Bay Views
House
Clearwater, FL, 33767, United States
0.5k from Diamond Isle center

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

6 Bedrooms18 Guests
10.0

Exceptional

3 reviews

$1984
Average price / night
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New-Luxury Resort Pool w/ Slide&Spa-Rooftop Views
New-Luxury Resort Pool w/ Slide&Spa-Rooftop Views
House
Clearwater, FL, 33767, United States
0.5k from Diamond Isle center

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

6 Bedrooms18 Guests
9.0

Fabulous

2 reviews

$2054
Average price / night
Check Availability
Luxury End-Unit Townhome: Private Elevator, Rooftop Hot Tub & Gulf Views
Luxury End-Unit Townhome: Private Elevator, Rooftop Hot Tub & Gulf Views
Condo
Clearwater, FL, 33767, United States
0.5k from Diamond Isle center

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

4 Bedrooms12 Guests
9.8

Exceptional

157 reviews

$617
Average price / night
Check Availability
Luxurious, Family Friendly House, Rooftop Terrace, Hot Tub & Breathtaking Views!
Luxurious, Family Friendly House, Rooftop Terrace, Hot Tub & Breathtaking Views!
House
Clearwater Beach, FL, 33767, United States
0.5k from Diamond Isle center

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

4 Bedrooms11 Guests
9.8

Exceptional

191 reviews

$595
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 Diamond Isle.

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Diamond Isle Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1191 verified family-friendly vacation rentals in Diamond Isle. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Diamond Isle vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $147 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Diamond Isle 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 Diamond Isle 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 Diamond Isle often include amenities such as Child Friendly, Kitchen, and Balcony/Terrace. 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.