
Family-friendly holiday rentals in Highland Beach
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Highland Beach
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Luxe 3-Bedroom Vacation Home|Pool|Blocks to Beach
JUST ACHIEVED COVETED TOP 1 % of all AIRBB Properties. Enjoy a magical beach vacation at this new-renovated, single-story home. Indulge in evening cocktails under the covered patio and enjoy a screened in, heated pool – completely pest-free! Inside, find a stylish living room, a modern kitchen, and three lovely bedrooms. Room for the whole family plus a MILE to the beach.Large Capacity Washer & Dryer 4 Min Drive to Island Water Sports 5 Min Drive to Beach 7 Min Drive to Mizner Park High Repeats

Beach Retreat-W/Cabana Service*Walk to Downtown*
Looking for the perfect romantic getaway? Look no further than this charming, newly renovated one-bedroom home in the most picturesque town on Florida’s coast. Enjoy the ocean breeze and azure waters of Delray Beach and live like locals as you enjoy being in historic downtown, stroll to the beaches, and enjoy the local attractions. 4 Min Walk to Pineapple grove + Atlantic Ave 4 Min Drive to Delray Beach 9 Min Drive to Wakodahatche Wetlands Learn More Below and Experience Delray Beach With Us!

Steps to Private Beach, Pool, Private Patio 19-3
Come stay at this beautifully furnished villa in the exclusive community of Highland Beach. Located directly across from the beach, minutes to Atlantic Avenue in Delray or Mizner Park in Boca Raton. High end finishes throughout in this single story villa showcasing 2 bedrooms, 2 full baths that sleeps 8! Enjoy the 2 car parking, fenced in patio, community pool and private beach access on A1A. Ease of access with only two steps at entry and a keyless entry smart lock. Pet friendly up to 2 pets!

ON CANAL! Pool+Walk to BEACH! Boat Watch! 1b/1b
Beautiful 1 bedroom condo located directly on the intracoastal with a heated pool. This unit DOES NOT have water view from the condo BUT has amazing views of the intracoastal waterway from the patio/pool area. Enjoy watching the yachts sail by along with taking in amazing sunsets from the dock. Work from home, 1 block from the beach! Quiet and peaceful. Within walking distance to many shops and local amenities! Perfect for couples, young families and groups of friends traveling together.

Cozy Delray Beach House Waterfront Intracoastal
🏝LOCATION, LOCATION, LOCATION! Delray Beach's BEAUTIFUL waterfront property! The Bamboo Beach House is located directly on Intracoastal waterway in Delray Beach. Each unit has private patio overlooking 40 ft of waterfront! Enjoy morning coffee and experience beautiful sunrises with the ocean breeze. Our piece of waterfront is a favorite area of local manatees to swim in with the tides, along with schools of jumping fish! The amazing water views and aquatic wildlife is second to none!

Spacious Designer Home Htd Pool Near Atlantic Ave
🌴 Enjoy this spacious Delray Beach retreat in Delray Beach, featuring a resort-style heated pool with sun shelf, fire pit, BBQ Ggill, cornhole, and a private backyard oasis. Inside, relax with soaring two-story living, fireplace, and modern open spaces. Comfortable bedrooms make it perfect for families and groups seeking fun, relaxation, and easy access to beaches and Atlantic Ave. Message us today and enjoy sunshine, space, and unforgettable memories — all in one perfect stay. 🌴☀️

shipwrecked fun design • stunning canal view
Bold interior design in this newly renovated pad with a beautiful canal and dock in delray. Step in the front door and immediately you see the large windows looking out onto the water in the back. This is true to Delray Beach with all its charm. Now pop on a movie on the big 75 inch Smart TV screen, rest your head on the comfy beds, shower under the rainfall fixtures and truly unwind in a Delray-geous getaway. Just 6 minutes to the beach or Delray's amazing nightlife and restaurants.

Happy Mango | Heated Pool | Walk to Atlantic Ave
Escape the winter chill and kick back in sunny Delray Beach! The Happy Mango Hideaway is a private 2-bedroom, pet-friendly cottage featuring a heated saltwater pool, spa-style bathroom (renovated Oct 2025), full kitchen, fast Wi-Fi, and cozy workspace. Walk to Atlantic Ave’s shops, cafés, and nightlife, or unwind in your fenced tropical yard. Perfect for holiday travelers, snowbirds, and remote workers seeking sunshine and serenity. Make Delray Beach your home for the holidays.

Retro charm studio - Walk to beach & Atlantic Ave
Charming studio with vintage vibes in a serene location near Atlantic Avenue—just a 2-minute walk to the beach and Opal Grand Beach Hotel. Step into a bygone era, radiating 1950s nostalgia in one of Delray Beach’s most coveted spots. Enjoy the Grove Condominiums' old-world charm, pool, and tropical gardens. Soak in Delray Beach's retro essence with upscale bars, diners, and boutique shops nearby. Embrace classic charm and coastal living in this slice of the '50s.

Lovely one bedroom apt. 1 block from beach
Location, location! Beach life! Just bring your suntan lotion. The property is located on the Boca raton Bch and Deerfield Bch line. So you have the option of a secluded Bch to relax at or the active beach with volleyball courts, shops , restaurants and and a melting pot of cultures. The Comfortable stylish apt is Steps away from the all this! Pvt yard with sitting area. It’s landscaped beautifully with flowering gardens. It’s your home away from home

Walk to Mizner/Brightline, Parking, Wi-Fi, Patio
Studio with outdoor patio including table, loungers and BBQ. Located in Downtown Boca: 8 minute walk to the Brightline train station, 7 blocks from popular Mizner Park, 1.9 miles from the beach and 1 mile from FAU. The safety of our guests is of utmost importance. We're taking every precaution & wipe down every surface with commercial grade disinfecting solution as we prepare for your stay.

Cozy and clean guesthouse in Boynton Beach
Completely renovated guest house located in a quite island neighborhood. Near many shopping stores and restaurants. 10 mins to the beach. Beautiful walking areas across from the community. Plenty of free parking space. We are 11 miles south of PALM BEACH AIRPORT, 32 miles north of FORT LAUDERDALE AIRPORT and 52 miles north from MIAMI INTERNATIONAL AIRPORT, we are just over a mile from I95.
Popular amenities for Highland Beach family-friendly rentals
Family-friendly home rentals with a hot tub

Key west suite with a hot tub and heated pool

Delray Bali House ~ Heated Pool ~ Sauna ~ Hot Tub

Curated Luxury Retreat | Pool • Spa • 8 min Beach

Waterfront: Heated Pool, Spa, wet bar & Boat Rides

Resort style 1BR/1BA condo

Private Guesthouse centrally located

2BR | Hot Tub W/ Peaceful Backyard • 1 Mi to Beach

Key West Style Suite with Pool/Spa
Family- and pet-friendly home rentals

Totally Private Studio, NO shared Spaces-Renovated

Walk to Beach*2 bedroom*Yard*Fully Renovated*Grill

Coco Loco Oasis w/Saline Pool Near Deerfield Beach

Renovated Home w/ Saltwater Pool & mins to beach

Charming Beach House with Pool! Great location!

Mango Beach! King Bed Suite/Near Atlantic Ave

Comfy Cozy Beachy Boho 1000 Steps to the Sand

Private cottage two blocks to Atlantic Ave.
Family-friendly home rentals with a pool

Heated Pool! Private Home+Bikes & Fire Pit!

Delray Sunshine Cottage w/ Private Backyard & Pool

Beach Studio Steps from Ocean & Atlantic Ave

Cozy 1BR | Steps from South Beach, Boca

Oceanfront Boca Oasis | Beach Gear | Pool &Jacuzzi

The Getaway 3BR/3BA Pool Home E. Delray

Really Big 1BR/BA w/ Pool; 1 Mile From Beach

Walk to beach pool and spa home
Quick stats about holiday rentals that are family-friendly in Highland Beach

Total holiday rentals
Explore 40 holiday rentals in Highland Beach

Nightly prices starting at
Highland Beach holiday rentals start at $155 AUD per night before taxes and fees

Verified guest reviews
Over 1,060 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Highland Beach holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Highland Beach rentals

4.8 Average rating
Highland Beach stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Rentals with pools Highland Beach
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- South Beach
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- Bayfront Park
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