Family-Friendly Vacation Rentals in Pineapple Grove Arts District, FL: Compare 10+ Sites & Save

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445 Best Family Vacation Rentals in Pineapple Grove Arts District (Starting from $142)

Delray Beach Getaway - Minutes to Beach & More
Delray Beach Getaway - Minutes to Beach & More
House
Delray Beach, FL, USA
0.3k from Pineapple Grove Arts District center

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

2 Bedrooms4 Guests
New to Booking
$213
Average price / night
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Private Cottage/Courtyard steps from Downtown Delray and The Chic Ray Hotel   <br>
Private Cottage/Courtyard steps from Downtown Delray and The Chic Ray Hotel <br>
House
Delray Beach, FL, 33444, United States
0.2k from Pineapple Grove Arts District center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

9 reviews

$241
Average price / night
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Let your Delray Beach Getaway Begin Here
Let your Delray Beach Getaway Begin Here
House
Delray Beach, FL, USA
0.3k from Pineapple Grove Arts District center

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

2 Bedrooms4 Guests
New to Booking
$205
Average price / night
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Luxury Retreat - Private Pool Cottage in Delray Beach – 45 Min to Hard Rock
Luxury Retreat - Private Pool Cottage in Delray Beach – 45 Min to Hard Rock
Cottage
Delray Beach, FL, 33444, United States
0.3k from Pineapple Grove Arts District center

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

2 Bedrooms4 Guests
10.0

Exceptional

13 reviews

$540
Average price / night
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Magnificent Beach Townhome Steps from Atlantic Ave
Magnificent Beach Townhome Steps from Atlantic Ave
House
Delray Beach, FL, USA
0.5k from Pineapple Grove Arts District center

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

2 Bedrooms6 Guests
New to Booking
$410
Average price / night
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Pool Views-Walk to Atlantic Ave
Pool Views-Walk to Atlantic Ave
House
Delray Beach, FL, 33483, United States
0.4k from Pineapple Grove Arts District center

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

2 Bedrooms4 Guests
9.8

Exceptional

65 reviews

$295
Average price / night
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Large 8 Beds 4 Bath Heated Pool House Delray Beach
Large 8 Beds 4 Bath Heated Pool House Delray Beach
House
Miami, FL, USA
0.5k from Pineapple Grove Arts District center

Guest Services, Air Conditioner, Barbecue/Outdoor Cooking, Parking, Internet, Ocean View, Security/Safety

7 Bedrooms29 Guests
New to Booking
$790
Average price / night
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Lux Exec 4/3.5- HTD Pool.  Walk everywhere- 3 blocks off \"The Ave\". Best loc!
Lux Exec 4/3.5- HTD Pool. Walk everywhere- 3 blocks off \"The Ave\". Best loc!
House
Delray Beach, FL, 33444, United States
0.4k from Pineapple Grove Arts District center

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

4 Bedrooms12 Guests
10.0

Exceptional

16 reviews

$1361
Average price / night
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Heated Pool-Spa & Putting Green! Walk to The Ave, 1mi to beach!
Heated Pool-Spa & Putting Green! Walk to The Ave, 1mi to beach!
House
Delray Beach, FL, USA
0.5k from Pineapple Grove Arts District center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$389
Average price / night
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Downtown Luxury Home + Guest Home w/ Heated Pool & Spa 3 blocks to Atlantic Ave
Downtown Luxury Home + Guest Home w/ Heated Pool & Spa 3 blocks to Atlantic Ave
House
Delray Beach, FL, 33444, United States
0.4k from Pineapple Grove Arts District center

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

3 Bedrooms8 Guests
10.0

Exceptional

10 reviews

$1088
Average price / night
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2 BD Delray Beach Cottage walk to The Ave & beach
2 BD Delray Beach Cottage walk to The Ave & beach
House
Delray Beach, FL, USA
0.6k from Pineapple Grove Arts District center

Internet, Pet Friendly, Air Conditioner, Parking, Balcony/Terrace, Child Friendly

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$142
Average price / night
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210 Managed By Brampton Park
210 Managed By Brampton Park
House
Delray Beach, FL, 33444, United States
0.5k from Pineapple Grove Arts District center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$870
Average price / night
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Historical Residence Heated Pool Beach Proximity Heron Key RESlDENCES
Historical Residence Heated Pool Beach Proximity Heron Key RESlDENCES
House
Delray Beach, FL, USA
0.6k from Pineapple Grove Arts District center

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

1 Bedroom8 Guests
New to Booking
$1352
Average price / night
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Luxury Tropical Family Oasis
Luxury Tropical Family Oasis
House
Delray Beach, FL, USA
0.6k from Pineapple Grove Arts District center

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

1 Bedroom7 Guests
New to Booking
$614
Average price / night
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Beachy Perfection - Walk to Atlantic Ave.
Beachy Perfection - Walk to Atlantic Ave.
House
Delray Beach, FL, 33483, United States
0.5k from Pineapple Grove Arts District center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

90 reviews

$429
Average price / night
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Pool and Spacious Backyard - Delray Beach Home
Pool and Spacious Backyard - Delray Beach Home
House
Delray Beach, FL, USA
0.7k from Pineapple Grove Arts District center

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

1 Bedroom6 Guests
New to Booking
$392
Average price / night
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⭐Only 5 Minutes To Beach ⭐ Downtown, Fast Wi-fi, Free Parking, Outdoor Grill
⭐Only 5 Minutes To Beach ⭐ Downtown, Fast Wi-fi, Free Parking, Outdoor Grill
Condo
Delray Beach, FL, 33444, United States
0.5k from Pineapple Grove Arts District center

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

1 Bedroom4 Guests
9.8

Exceptional

11 reviews

$255
Average price / night
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2 mins to Downtown Atlantic Ave-3 mins to Beach-600mbps-BBQ-Fenced Yard
2 mins to Downtown Atlantic Ave-3 mins to Beach-600mbps-BBQ-Fenced Yard
House
Delray Beach, FL, USA
0.8k from Pineapple Grove Arts District center

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

3 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$266
Average price / night
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Stylish retreat w/pool, BBQ & concierge
Stylish retreat w/pool, BBQ & concierge
House
Delray Beach, FL, 33483, United States
0.6k from Pineapple Grove Arts District center

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

3 Bedrooms7 Guests
New to Booking
$767
Average price / night
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Spacious Villa Azul
Spacious Villa Azul
Villa
Delray Beach, FL, USA
0.9k from Pineapple Grove Arts District center

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

2 Bedrooms6 Guests
9.5

Superb

2 reviews

$375
Average price / night
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Delray Beach Upscale Home with Heated Pool, close to Atlantic Ave and Beach
Delray Beach Upscale Home with Heated Pool, close to Atlantic Ave and Beach
House
Delray Beach, FL, 33483, United States
0.6k from Pineapple Grove Arts District center

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

4 Bedrooms8 Guests
9.4

Superb

16 reviews

$1043
Average price / night
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Luxury Villa Nicole
Luxury Villa Nicole
Villa
Delray Beach, FL, USA
0.9k from Pineapple Grove Arts District center

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

2 Bedrooms6 Guests
8.0

Good

3 reviews

$337
Average price / night
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Heated Saltwater Pool, Spacious home, Close to Altantic Ave & Beach!
Heated Saltwater Pool, Spacious home, Close to Altantic Ave & Beach!
House
Delray Beach, FL, 33444, United States
0.6k from Pineapple Grove Arts District center

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

4 Bedrooms8 Guests
10.0

Exceptional

85 reviews

$499
Average price / night
Check Availability
3 blocks from Downtown Atlantic Ave - 1 mile to Beach - Safe area
3 blocks from Downtown Atlantic Ave - 1 mile to Beach - Safe area
House
Delray Beach, FL, 33483, United States
0.6k from Pineapple Grove Arts District center

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

3 Bedrooms8 Guests
10.0

Exceptional

43 reviews

$266
Average price / night
Check Availability
2 Bed Cottage walk to Pineapple Grove, Atlantic Ave & the Beach
2 Bed Cottage walk to Pineapple Grove, Atlantic Ave & the Beach
House
Delray Beach, FL, 33444, United States
0.6k from Pineapple Grove Arts District center

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

2 Bedrooms6 Guests
9.0

Fabulous

4 reviews

$234
Average price / night
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2 BD Delray Beach Cottage walk to Atlantic Ave & the beach
2 BD Delray Beach Cottage walk to Atlantic Ave & the beach
House
Delray Beach, FL, 33444, United States
0.6k from Pineapple Grove Arts District center

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

9.0

Fabulous

2 reviews

$224
Average price / night
Check Availability
Spacious 8-bedroom house in Delray Beach Steps From Atlantic Av. Heated Pool.
Spacious 8-bedroom house in Delray Beach Steps From Atlantic Av. Heated Pool.
House
Delray Beach, FL, 33444, United States
0.7k from Pineapple Grove Arts District center

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

7 Bedrooms16 Guests
8.0

Good

2 reviews

$711
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 Pineapple Grove Arts District.

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Frequently Asked Questions

You can explore 445 verified family-friendly vacation rentals in Pineapple Grove Arts District. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Pineapple Grove Arts District vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $142 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Pineapple Grove Arts District 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 Pineapple Grove Arts District 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 Pineapple Grove Arts District often include amenities such as Child Friendly, View, 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.