Family-friendly vacation rentals in Delray Beach

5 out of 5 average rating, 36 reviews

210 Walk to Pineapple Grove | by Brampton Park

Exclusively Managed By Brampton Park Heated Pool and Pet Friendly 4 Bedroom 3 Bathroom Delightful home, less than 1 mile to the Beach Modern, upscale downtown Delray home, fully renovated with all new furnishings as of July 2024. While this home is on a quiet residential street, the location is truly unbeatable - 1/4 mile to Pineapple Grove district that is bustling with restaurants, bars and cafes, and The Ray Hotel. Half a mile to Atlantic Avenue, and less than 1 mile to the beach.

Indoor spacesFamilyComfort

A private dock extends over tranquil waters, framed by lush palm trees. Two blue chairs are positioned on a wooden deck, offering a serene space to enjoy the surrounding nature and canal views. The sky is clear with soft clouds reflecting on the water's surface.

4.98 out of 5 average rating, 227 reviews

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.

Indoor spacesKitchenBathroom

Beach chairs are set up under large blue umbrellas on white sand. The tranquil ocean waves can be seen in the distance, blending into a clear sky with soft clouds. A sign indicates that a beach membership is included with the stay.

4.9 out of 5 average rating, 155 reviews

Downtown Beach Home w/FREE Beach Cabana membership

Whether you're looking for a winter escape or a much-deserved getaway, our professionally designed, well-appointed, & newly renovated home was created with your family and friends in mind! Enjoy the warm tropical air and Caribbean blue waters of Delray Beach and all of the entertainment and nightlife that Atlantic Ave has to offer. This experience is all about fun in the sun, first-class food and drink, and plenty of laughs with your loved ones. We look forward to hosting you!

KitchenFamilyShared spaces

Superhost

A heated pool invites relaxation, surrounded by a serene yard with tropical palm trees. Colorful floats rest on the water's surface, while sun loungers and conversation chairs provide ample seating for enjoying the outdoors.

4.93 out of 5 average rating, 145 reviews

Heated Pool | King Bd | Cozy Backyard | Quiet Stay

Feel right at home at The Royal House, nestled in a peaceful neighborhood perfect for a relaxing family retreat. Experience year-round enjoyment with our heated pool, ensuring an endless swimsuit season. Whether it's day or night, warm or cool, the pool is ready for you to dive in and unwind in a private and peaceful setting. Ideal location: 10 minute drive - Downtown Atlantic Ave 10 minute drive - Beach 5 minute drive - Kings Point 5 minute drive - I-95 & Turnpike

KitchenFamilyParking

4.99 out of 5 average rating, 114 reviews

Cottage in Delray Beach

Private Pool Oasis | Steps to Atlantic Ave

Escape to your own private tropical retreat in the heart of Delray Beach. The Happy Mango Hideaway is a fully private, pet-friendly 2-bedroom cottage featuring a heated saltwater pool, a spa-inspired bathroom (renovated in 2025), a full kitchen, fast Wi-Fi, and a workspace. Spend your days exploring Atlantic Avenue's restaurants, boutiques, galleries, and beaches, all just minutes away. Then return home to relax by the pool and enjoy your private backyard oasis.

FamilyIndoor spacesCheckout

An aerial view showcases a modern home painted in soft turquoise, surrounded by lush greenery. A sparkling pool is framed by neatly manicured grass, and two umbrellas provide shade over outdoor seating. The inviting atmosphere is complemented by palm trees and a pop of vibrant colors.

4.96 out of 5 average rating, 113 reviews

The Dream 4 BR En-suite Pool Home close to beach

Dreams Delray is a modern 4 bedroom 4 1/2 bathroom (4 Bedroom En Suites) heated pool home which is a 10 minute walk to "The Ave,” Delray Beach's popular downtown venue, and a short 5 minute drive to our famous sandy beaches. It has everything you can ask for the perfect family vacation or a small getaway to sunny Florida. The home offers a top chef kitchen open floor plan, surround sound and a wonderful view of the pool from just about every part of the house.

KitchenIndoor spacesOutdoor spaces

Superhost

5 out of 5 average rating, 4 reviews

Lux Spa Retreat | Sauna, Plunge, Yoga, Pickleball

Escape to Raha, our brand-new wellness retreat in the heart of Delray Beach, sleeping 14 across 4 bedrooms. The backyard is the star: heated pool, hot tub, barrel sauna, cold plunge, pickleball court, and a tiki hut. Mornings in the sauna, evenings by the pool, all minutes from the beach and Atlantic Ave. Made for reunions, friends' trips, and the kind of getaway you don't need to recover from. Come rest, reset, and restore. - Stays by Nur x Soham Group

KitchenIndoor spacesComfort

4.87 out of 5 average rating, 181 reviews

An aerial view captures the vibrant coastal community, with the beach visible in the distance. The surrounding area features a mix of residential buildings, marinas, and lush greenery. The blue waters of the ocean contrast against the rooftops, offering a sense of tranquility and relaxation.

Cottage in Delray Beach

B.E.A.C.H. Best Escape Anyone Could Have. 2br/2bth

This is the Best Escape Anyone Could Have. Grab your towel and stroll to one of the best beaches in the United States. Don't forget the beach pass! It provides 2 lounge chairs and an umbrella. Afterwards, this cozy home awaits you. Its perfect location makes it difficult to decide whether to spend the evening in or out on the town. Fine dining and nightlife are just around the corner! Wherever your evening takes you, you're guaranteed to enjoy it!

Indoor spacesKitchenCheckout

4.97 out of 5 average rating, 33 reviews

Heated Pool, Hot Tub, Pickleball & Putting Green

Discover your own piece of paradise just minutes from Delray Beach’s vibrant Atlantic Avenue and pristine shoreline. This modern 4-bedroom home is ideal for large families, groups, or corporate retreats. Lounge by the private heated pool, unwind in the hot tub, challenge friends on the pickleball court or putting green, catch your favorite shows on a TV in every bedroom, or gather for a memorable feast in the state-of-the-art kitchen.

Indoor spacesFamilyBackyard

4.94 out of 5 average rating, 161 reviews

Waterfront, Spa, Htd Pool, Billiards, Lanai, Canal

Bachelorette weekends, birthday trips, family vacations — this is the house groups keep coming back to. Heated pool and spa on a private canal, screened lanai with string lights, billiards, and a dock where guests watch the sun go down. Sleeps 10. Hosts respond in minutes and know every great restaurant and hidden gem in Delray. 5 minutes to Atlantic Ave. Kayaks, paddleboards, and fishing gear included. 5 minutes to the beach.

KitchenFamilyDecor

Superhost

A resort-style heated pool is surrounded by lush palm trees and wooden fencing for privacy. Yellow umbrellas provide shade over lounge chairs, while a dining area is located nearby. The pool area is inviting, featuring inflatable pool floats resting on the water.

4.97 out of 5 average rating, 136 reviews

Honey Hole & Bear Den| Heated Pool | Delray Beach

Welcome to the Honey Hole! This family-friendly beach getaway is sure to have any guest relaxing all year round. Situated in a quiet and private neighborhood this home is perfect for all your vacation needs. This completely renovated home is a 5 minute drive down Atlantic Avenue to downtown and the beaches. You can find restaurants, shops, parks, boat tours, and much more locally. We look forward to hosting you!

FamilyKitchenValue

The exterior of the vacation home is illuminated in soft lighting, highlighting tropical landscaping and palm trees. A spacious driveway leads to the entrance, while large windows suggest a welcoming interior.