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

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  3.  USA

  4.  Florida
  5.  Fort Walton Beach - Destin
  6.  Holiday Isle

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4163 Best Family Vacation Rentals in Holiday Isle (Starting from $323)

Palm Breeze - Is a 4BR with Private Pool and Boat Dock in Destin
Palm Breeze - Is a 4BR with Private Pool and Boat Dock in Destin
House
Destin, FL, USA
0.1k from Holiday Isle center

Accommodations, Pools, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay, Family

4 Bedrooms12 Guests
New to Booking
$1495
Average price / night
Check Availability
Deep water 100ft dock/shore power! 3 min to beach, pool, jacuzzi, cart, ice!
Deep water 100ft dock/shore power! 3 min to beach, pool, jacuzzi, cart, ice!
House
Destin, FL, 32541, United States
0.0k from Holiday Isle center

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

5 Bedrooms12 Guests
10.0

Exceptional

17 reviews

$1103
Average price / night
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Marlin Haven at Holiday Isle
Marlin Haven at Holiday Isle
House
Destin, FL, USA
0.1k from Holiday Isle center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

6 Bedrooms16 Guests
New to Booking
$1685
Average price / night
Check Availability
Waterfront Home w/ Pool, Boat Slip & Private Beach Access – Holiday Isle
Waterfront Home w/ Pool, Boat Slip & Private Beach Access – Holiday Isle
House
Destin, FL, 32541, United States
0.1k from Holiday Isle center

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

6 Bedrooms20 Guests
10.0

Exceptional

11 reviews

$653
Average price / night
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Waterfront Dream House Pool Golf Cart & Dock
Waterfront Dream House Pool Golf Cart & Dock
House
Destin, FL, USA
0.1k from Holiday Isle center

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

1 Bedroom16 Guests
New to Booking
$1832
Average price / night
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Yellowfin Place | On the Water | Harbor Access | Pool | Pet Friendly | Free Fun Pass
Yellowfin Place | On the Water | Harbor Access | Pool | Pet Friendly | Free Fun Pass
House
Destin, FL, 32541, United States
0.1k from Holiday Isle center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area

4 Bedrooms12 Guests
New to Booking
$617
Average price / night
Check Availability
Destin Beach House - Happy Harbor House by Panhandle Getaways
Destin Beach House - Happy Harbor House by Panhandle Getaways
House
Destin, FL, USA
0.1k from Holiday Isle center

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

4 Bedrooms12 Guests
4.0

Review score

1 reviews

$1183
Average price / night
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Boat Slip, Private Pool and Spa, Pet Friendly, Private Beach Access
Boat Slip, Private Pool and Spa, Pet Friendly, Private Beach Access
House
Destin, FL, 32541, United States
0.1k from Holiday Isle center

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

3 Bedrooms8 Guests
9.8

Exceptional

99 reviews

$735
Average price / night
Check Availability
Aegean #329
Aegean #329
Apartment
Destin, FL, USA
0.2k from Holiday Isle center

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

3 Bedrooms8 Guests
New to Booking
$627
Average price / night
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Marlin Haven @ Holiday Isle | Luxury Home | Private Pool & Spa | Walk to Beach | 6BR Coastal Gem
Marlin Haven @ Holiday Isle | Luxury Home | Private Pool & Spa | Walk to Beach | 6BR Coastal Gem
House
Destin, FL, 32541, United States
0.1k from Holiday Isle center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area

6 Bedrooms16 Guests
9.6

Exceptional

10 reviews

$1174
Average price / night
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The Back Porch - Is a relaxing 4 bedroom 3 bathroom House on Holiday Isle
The Back Porch - Is a relaxing 4 bedroom 3 bathroom House on Holiday Isle
House
Destin, FL, USA
0.2k from Holiday Isle center

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

4 Bedrooms12 Guests
8.0

Good

2 reviews

$323
Average price / night
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Destin Beach House - Private Pool - Pet Friendly, Boat Slip, Beach, Sleeps 12
Destin Beach House - Private Pool - Pet Friendly, Boat Slip, Beach, Sleeps 12
House
Destin, FL, 32451, United States
0.1k from Holiday Isle center

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

4 Bedrooms12 Guests
9.0

Fabulous

14 reviews

$1008
Average price / night
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Boaters Dream House On Holiday Isle
Boaters Dream House On Holiday Isle
House
Destin, FL, USA
0.2k from Holiday Isle center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay

5 Bedrooms10 Guests
New to Booking
$999
Average price / night
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Destin Harbor Haven sleeps 8, pet friendly, near beach
Destin Harbor Haven sleeps 8, pet friendly, near beach
House
Destin, FL, 32541, United States
0.2k from Holiday Isle center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$405
Average price / night
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Casa Palmas On Holiday Isle
Casa Palmas On Holiday Isle
House
Destin, FL, USA
0.2k from Holiday Isle center

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

3 Bedrooms6 Guests
New to Booking
$874
Average price / night
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BEACH BOATING PARADISE-Heated Pool,2 King Suites,90ft Dock,Game Room,Bikes,5Star
BEACH BOATING PARADISE-Heated Pool,2 King Suites,90ft Dock,Game Room,Bikes,5Star
Villa
Destin, FL, 32541, United States
0.2k from Holiday Isle center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

6 Bedrooms16 Guests
10.0

Exceptional

70 reviews

$1254
Average price / night
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Aegean 327
Aegean 327
Apartment
Destin, FL, USA
0.2k from Holiday Isle center

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

3 Bedrooms10 Guests
New to Booking
$843
Average price / night
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Inlet Reef Club 612 - Beach view luxury condo in Destin
Inlet Reef Club 612 - Beach view luxury condo in Destin
Condo
Destin, FL, 32541, United States
0.2k from Holiday Isle center

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

2 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$557
Average price / night
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Stunning Gulf Views
Stunning Gulf Views
House
Destin, FL, USA
0.2k from Holiday Isle center

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

2 Bedrooms6 Guests
New to Booking
$464
Average price / night
Check Availability
This property is no longer for rent.  It has been removed from the program.
This property is no longer for rent. It has been removed from the program.
Condo
Destin, FL, 32541, United States
0.2k from Holiday Isle center

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

2 Bedrooms8 Guests
9.8

Exceptional

13 reviews

$593
Average price / night
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Private paradise, quiet, renovated, views from every floor. Steps to the gulf!
Private paradise, quiet, renovated, views from every floor. Steps to the gulf!
Condo
Destin, FL, 32541, United States
0.2k from Holiday Isle center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Elevator, Extra Bed, Free Parking, Heater

4 Bedrooms10 Guests
9.6

Exceptional

38 reviews

$429
Average price / night
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Deep water access w/ 65ft inland slip! Private Beach access! Water Taxi!
Deep water access w/ 65ft inland slip! Private Beach access! Water Taxi!
House
Destin, FL, 32541, United States
0.2k from Holiday Isle center

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

5 Bedrooms12 Guests
10.0

Exceptional

39 reviews

$797
Average price / night
Check Availability
The Destin Boathouse|Easy Beach Access|Private Pool on Canal with Dock Access
The Destin Boathouse|Easy Beach Access|Private Pool on Canal with Dock Access
House
Destin, FL, 32541, United States
0.3k from Holiday Isle center

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

8 Bedrooms18 Guests
10.0

Exceptional

4 reviews

$1558
Average price / night
Check Availability
Aegean 111 sleeps 8 near beach
Aegean 111 sleeps 8 near beach
House
Destin, FL, 32541, United States
0.3k from Holiday Isle center

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

2 Bedrooms8 Guests
New to Booking
$553
Average price / night
Check Availability
Tropical Oasis and private beach on the exclusive Holiday Isle in Destin, FL
Tropical Oasis and private beach on the exclusive Holiday Isle in Destin, FL
Condo
Destin, FL, 32541, United States
0.3k from Holiday Isle center

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

3 Bedrooms10 Guests
9.6

Exceptional

129 reviews

$480
Average price / night
Check Availability
Freshly painted, new  flooring -RELAX, RELAX  THIS VIEW IS DIRECTLY ON THE BEACH
Freshly painted, new flooring -RELAX, RELAX THIS VIEW IS DIRECTLY ON THE BEACH
Condo
Destin, FL, 32541, United States
0.3k from Holiday Isle center

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

3 Bedrooms10 Guests
10.0

Exceptional

38 reviews

$587
Average price / night
Check Availability
Best Gulf-Front Beach View in Destin!  Best designed condo 2015*
Best Gulf-Front Beach View in Destin! Best designed condo 2015*
Condo
Destin, FL, 32541, United States
0.3k from Holiday Isle center

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

2 Bedrooms6 Guests
9.4

Superb

136 reviews

$392
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 Holiday Isle.

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Holiday Isle Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 4163 verified family-friendly vacation rentals in Holiday Isle. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Holiday Isle vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $323 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Holiday 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 Holiday 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 Holiday Isle often include amenities such as Fireplace/Heating, 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.