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

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  2. Family Vacation Rentals
  3.  USA

  4.  Florida
  5.  Pensacola
  6.  Holiday Harbor

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1471 Best Family Vacation Rentals in Holiday Harbor (Starting from $116)

Heron's Nest
Heron's Nest
House
Perdido Key, FL, USA
0.1k from Holiday Harbor center

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

3 Bedrooms9 Guests
6.8

Good

6 reviews

$193
Average price / night
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Luxurious 4-BR Beachfront Escape: Private Beach, Fishing Dock, Boat & Family Fun
Luxurious 4-BR Beachfront Escape: Private Beach, Fishing Dock, Boat & Family Fun
House
Pensacola, FL, 32507, United States
0.1k from Holiday Harbor center

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

4 Bedrooms12 Guests
9.0

Fabulous

9 reviews

$770
Average price / night
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Serene Pensacola Vacation Rental with Gas Grill
Serene Pensacola Vacation Rental with Gas Grill
House
Pensacola, FL, USA
0.1k from Holiday Harbor center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

4 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$608
Average price / night
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Serene Pensacola Vacation Rental w/ Gas Grill
Serene Pensacola Vacation Rental w/ Gas Grill
House
Pensacola, FL, 32507-9633, United States
0.1k from Holiday Harbor center

AC, Barbecue, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

4 Bedrooms8 Guests
9.6

Exceptional

8 reviews

$382
Average price / night
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Lucky View Beach House
Lucky View Beach House
House
Pensacola, FL, USA
0.3k from Holiday Harbor center

Cheap, Accommodations, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms15 Guests
9.0

Fabulous

2 reviews

$481
Average price / night
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\"Lucky View\" | Private Pool | Boat Dock | Waterfront | Beach Getaways
\"Lucky View\" | Private Pool | Boat Dock | Waterfront | Beach Getaways
House
Pensacola, FL, 32507, United States
0.3k from Holiday Harbor center

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

3 Bedrooms15 Guests
9.0

Fabulous

4 reviews

$1420
Average price / night
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Perdido Escape Spacious 3BR 3BA Condo Beach Pool
Perdido Escape Spacious 3BR 3BA Condo Beach Pool
Apartment
FL, USA
0.4k from Holiday Harbor center

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

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$400
Average price / night
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Perdido Key Private Paradise-Private Beach-Pool-Free Daily Activities
Perdido Key Private Paradise-Private Beach-Pool-Free Daily Activities
Condo
Pensacola, FL, 32507, United States
0.4k from Holiday Harbor center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$341
Average price / night
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San Andres Unit A205 at Lost Key Golf & Beach Club
San Andres Unit A205 at Lost Key Golf & Beach Club
House
Pensacola, FL, USA
0.4k from Holiday Harbor center

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

3 Bedrooms8 Guests
New to Booking
$214
Average price / night
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Perdido Key Water View with Pool, Second Floor Duplex
Perdido Key Water View with Pool, Second Floor Duplex
Condo
Pensacola, FL, 32507, United States
0.4k from Holiday Harbor center

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

2 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$218
Average price / night
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Sailmakers place 206
Sailmakers place 206
House
FL, USA
0.4k from Holiday Harbor center

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

3 Bedrooms6 Guests
New to Booking
$310
Average price / night
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Perfect For Families, Private beach, Pool, Game Room, all King beds
Perfect For Families, Private beach, Pool, Game Room, all King beds
House
Pensacola, FL, 32507, United States
0.7k from Holiday Harbor center

AC, Arcade, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

5 Bedrooms10 Guests
9.6

Exceptional

40 reviews

$708
Average price / night
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Lost Key 403A
Lost Key 403A
Apartment
Perdido Key, FL, USA
0.4k from Holiday Harbor center

Apartments, Accommodations, Pools, 4-star, Lodgings, Hot tubs, Places to stay

3 Bedrooms8 Guests
New to Booking
$116
Average price / night
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PINK PEARL of THE POINT --Affordable 3 / 2  One block to ICW--6 minutes to Beach
PINK PEARL of THE POINT --Affordable 3 / 2 One block to ICW--6 minutes to Beach
House
Pensacola, FL, 32507, United States
0.7k from Holiday Harbor center

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

3 Bedrooms8 Guests
10.0

Exceptional

29 reviews

$231
Average price / night
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Santo Amaro 801B - Lost Key Golf & Beach
Santo Amaro 801B - Lost Key Golf & Beach
Apartment
Holiday Harbor, Pensacola, Florida, USA
0.4k from Holiday Harbor center

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

3 Bedrooms7 Guests
New to Booking
$292
Average price / night
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Perdido Key Home w/ Bay Access < 1 Mi to Beach!
Perdido Key Home w/ Bay Access < 1 Mi to Beach!
House
Pensacola, FL, 32507, United States
0.8k from Holiday Harbor center

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

4 Bedrooms8 Guests
New to Booking
$219
Average price / night
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Lost Key 14338 Beach Heather Ct By Pkrm
Lost Key 14338 Beach Heather Ct By Pkrm
Apartment
Pensacola, FL, USA
0.4k from Holiday Harbor center

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

2 Bedrooms8 Guests
New to Booking
$278
Average price / night
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Warm Winter Escape, Spacious 4BR Home, Pool, Walk to the Beach!
Warm Winter Escape, Spacious 4BR Home, Pool, Walk to the Beach!
House
Pensacola, FL, 32507, United States
0.8k from Holiday Harbor center

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

4 Bedrooms14 Guests
8.8

Fabulous

8 reviews

$652
Average price / night
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Santo Amaro #705B at Lost Key
Santo Amaro #705B at Lost Key
Apartment
Perdido Key, FL, USA
0.4k from Holiday Harbor center

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

3 Bedrooms8 Guests
New to Booking
$319
Average price / night
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Perfectly Positioned: Banana Bay Resort's Home Close to Everything You Need!
Perfectly Positioned: Banana Bay Resort's Home Close to Everything You Need!
Condo
Pensacola, FL, 32507, United States
0.8k from Holiday Harbor center

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

3 Bedrooms10 Guests
9.0

Fabulous

20 reviews

$396
Average price / night
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Beach 6 min. drive, Bay Access 2 blocks away, RV Hookup in Driveway
Beach 6 min. drive, Bay Access 2 blocks away, RV Hookup in Driveway
House
Pensacola, FL, 32507, United States
0.9k from Holiday Harbor center

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

4 Bedrooms12 Guests
10.0

Exceptional

5 reviews

$248
Average price / night
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\"MEMORY MAKER PERDIDO\" 4/3.5. Sleeps 12. Walk to pool. Close to bay and beach.
\"MEMORY MAKER PERDIDO\" 4/3.5. Sleeps 12. Walk to pool. Close to bay and beach.
House
Pensacola, FL, 32507, United States
0.9k from Holiday Harbor center

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

4 Bedrooms12 Guests
10.0

Exceptional

27 reviews

$655
Average price / night
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DreamBoat Paradise-Spacious, Heated Pool, HotTub, Backyard Boat Slip, near Beach
DreamBoat Paradise-Spacious, Heated Pool, HotTub, Backyard Boat Slip, near Beach
House
Pensacola, FL, 32507, United States
0.9k from Holiday Harbor center

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

4 Bedrooms12 Guests
10.0

Exceptional

45 reviews

$572
Average price / night
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New! 5 min to beach! Clean, modern and spacious-King mattress on Primary room
New! 5 min to beach! Clean, modern and spacious-King mattress on Primary room
House
Pensacola, FL, 32507, United States
0.9k from Holiday Harbor center

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

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$311
Average price / night
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Walk / Bike to the Beach from Luxury Retreat w/pool!  2 Masters, Views, Cruisers
Walk / Bike to the Beach from Luxury Retreat w/pool! 2 Masters, Views, Cruisers
House
Pensacola, FL, 32507, United States
1.0k from Holiday Harbor center

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

4 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$728
Average price / night
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Desired Lost Key community- walk to beach & golf course + tons of amenities!
Desired Lost Key community- walk to beach & golf course + tons of amenities!
House
Pensacola, FL, 32507, United States
1.0k from Holiday Harbor center

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

2 Bedrooms6 Guests
New to Booking
$355
Average price / night
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Bring your boat.Just steps from your own Private Dock on the ICW in Perdido Key
Bring your boat.Just steps from your own Private Dock on the ICW in Perdido Key
House
Pensacola, FL, 32507, United States
1.0k from Holiday Harbor center

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

3 Bedrooms10 Guests
9.8

Exceptional

50 reviews

$530
Average price / night
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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 Harbor.

Stay Near Holiday Harbor's Top Attractions

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

Holiday Harbor Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1471 verified family-friendly vacation rentals in Holiday Harbor. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Holiday Harbor vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $116 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Holiday Harbor 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 Harbor 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 Harbor often include amenities such as Child Friendly, View, and Wellness Facilities. 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.