Family-friendly holiday rentals in Delray Beach

Guesthouse in Delray Beach

Beach chairs and umbrellas are arranged on a sandy shore, ready for relaxation. The living area features a comfortable sofa facing a vibrant teal media console, while the bedroom showcases a tranquil blue theme with a spacious bed. A private balcony offers outdoor seating.

4.94 out of 5 average rating, 218 reviews

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!

The living area features a comfortable grey sofa and two blue accent chairs arranged around a large area rug. A flat screen TV is mounted on the wall opposite, alongside a console table. Natural light streams through windows, enhancing the inviting ambiance.

4.99 out of 5 average rating, 77 reviews

Ocean Beach! King Bed Suite/Near Atlantic Ave

"Ocean Beach." Beautifully renovated and decorated for the most discerning guests. Take a refreshing ride to the beach on one of our new beach cruisers, approximately a half mile. You may also choose a relaxing walk to the mature dining, entertainment, and artsy scene of Atlantic Ave. Retreat back to rest on our new memory foam mattresses, with all white linens and towels. Or, enjoy the outdoor Bar BQ for a quiet night at home. Family friendly. Across from a lovely park. NO SMOKERS PLEASE.

A charming bungalow is surrounded by lush greenery, featuring a brick pathway leading to the entrance. Potted plants with colorful flowers are placed beside the door. The metal roof reflects sunlight, while the blue sky and clouds provide a serene backdrop.

4.93 out of 5 average rating, 219 reviews

Charming Beach House with Pool! Great location!

Stroll or bike to beautiful beach and Atlantic Avenue! Please contact me for bookings and availability for short term rentals with a 3 night minimum. 2 beautifully furnished bedrooms with queen beds, 1.5 baths plus outdoor shower. Cable TV and wifi, new linens, pots and pans and appliances. Large outdoor entertainment space with pool, waterfall, gas grill, tropical landscape! A true gem! I also add a pet fee of $150 per pet. We offer instant booking up to one year in advance of your stay.

4.95 out of 5 average rating, 110 reviews

An inviting outdoor space features a heated salt-water pool with a built-in fountain illuminated in soft purple light. Lounge chairs line the pool area, shaded by vibrant red umbrellas. Marble pavers surround the pool, providing a spacious area for relaxation and enjoyment.

Home in Boca Raton

Luxury Vacation Home -Private pool, Outdoor living

This Luxurious private home in beautiful Boca Raton is only a short drive to the beach. Enjoy ultimate privacy in our brand new heated pool and jacuzzi. Plenty of shopping and restaurants all within minutes. Kick back and relax in this newly renovated, ultra private, luxury vacation home. Just bring your suitcase and bathing suit and enjoy! Fully stocked kitchen with all you'll need........Indoor or out. Desk/ Workstation for home office and five oversized Smart TV's for entertainment.

4.93 out of 5 average rating, 75 reviews

The exterior of a yellow studio apartment is visible, showcasing a welcoming entrance framed by lush greenery. A colorful surfboard is positioned beside the door, and outdoor furniture is arranged on the shaded patio, inviting relaxation.

Condo in Delray Beach

Oceanfront Elegance - Sun Sand & Style

With a stay at Coral Cove, you'll be on the beach, steps from the chic shops and restaurants of Atlantic Avenue, a 5 minute drive to the Delray Beach Tennis Center and Tiger Woods PopStroke golfing. You’ll enjoy the nautical flavor of the studio apartment, the comfortable queen bed with coastal linens, the modern kitchen, and the full bath with tub. Great outdoor patio for barbecues or just to enjoy a glass of wine. Beach chairs and towels are available. Come join us in sunny Florida!

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.

4.99 out of 5 average rating, 204 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.

A private backyard features a heated pool surrounded by sun loungers and a thatched tiki hut. Soft lighting enhances the serene atmosphere, while palm trees and a grassy area create a tranquil oasis. A stunning sunset sky adds color to the scene.

4.93 out of 5 average rating, 120 reviews

Delray Bali House ~ Heated Pool ~ Sauna ~ Hot Tub

☆ 5% Military and First Responder Discount ☆ Escape to our Bali inspired oasis in the heart of Delray Beach! Immerse yourself in the city's vibrant culture while enjoying the local dining and shopping scene. Take a quick ride to the pristine beach for a fun-filled day of swimming, paddle-boarding, and boating, or head over to Lake Ida for a peaceful fishing trip. Unwind in the tranquil amenity filled backyard. Rejuvenate and make long lasting memories with your loved ones. Welcome!

4.99 out of 5 average rating, 104 reviews

Cottage in Delray Beach

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.

4.87 out of 5 average rating, 233 reviews

Condo in Delray Beach

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.

The private pool area showcases a sparkling blue pool, complete with a spa and sun loungers beneath vibrant red umbrellas. Lush greenery and tranquil waterfront views create a serene atmosphere, inviting relaxation and enjoyment under a bright blue sky with fluffy white clouds.

4.95 out of 5 average rating, 139 reviews

Waterfront Htd Pool, Spa, Billiards, Lanai, Canal

🌴 Relax at this luxury waterfront Delray Beach retreat in Delray Beach, featuring a heated pool & spa, private dock, screened porch with string lights & Smart TV, pool table, BBQ, and canal views. Bright open living and flexible sleeping for up to 10 guests make it perfect for families and groups seeking comfort, space, and true South Florida relaxation. Message us today and enjoy waterfront luxury, sunshine, and relaxation — all in one exceptional stay. 🌴☀️

Guesthouse in Delray Beach

A sandy pathway leads through lush green vegetation toward the beach, flanked by palm trees. A vibrant sunset casts an orange and pink hue across the sky, creating a picturesque backdrop against the ocean horizon.

4.86 out of 5 average rating, 251 reviews

4 Bed on the Water - Luxury Beach Retreat

Perfect location in Delray Beach. Steps to the sand and just a short walk to Atlantic Avenue shops, bars, restaurants, and attractions. High speed wireless internet and HD DirecTV with DVR in every bedroom! Plenty of beach towels and sunscreen provided! Granite countertops in kitchen and bathrooms. Stainless Steel Appliances. Beach entrance is near kayak rentals, volleyball courts, surf/paddle board rentals, and plenty of cabanas. Parking spot included.

The outdoor area features a heated pool surrounded by a spacious patio, with sun loungers placed nearby. A spa is integrated into the pool design. The house showcases large windows and architectural details, with soft evening light illuminating the space.

5 out of 5 average rating, 11 reviews

944 Large Home in Tropic Isles | by Brampton Park

Exclusively Managed by Brampton Park Heated Pool, Pet Friendly 4 Bedroom 3.5 Bathroom Family Home located in Tropic Isles Expansive views of the water from the backyard and master suite, and bedroom 3 (with balcony) High end furnishings and appliances throughout Beautiful formal living room with wet bar and cozy family room with large TV and sound bar Cafe, restaurants just 1/2 a mile away, Fresh market *Use of the Dock requires Prior Approval*

Popular amenities for Delray Beach family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 222 reviews

A serene outdoor area features a winding pool and a hot tub, surrounded by vibrant tropical landscaping. A thatched-roof tiki bar offers shaded seating, with lounging areas designated by comfortable furniture. The backdrop is filled with lush greenery, creating a private oasis.

Home in Deerfield Beach

Island Oasis Home in Deerfield Beach

A serene private backyard features a new salt system pool complemented by a spa. A slide leads into the pool from a deck. Lush greenery surrounds the area, providing privacy, with a well-maintained lawn and spacious patio areas ideal for relaxation.

4.91 out of 5 average rating, 35 reviews

Pool Paradise in Delray Beach

An elegantly designed spa area features a large, deep soaking tub at the center, surrounded by intricate stonework. Soft lighting highlights the textured walls, while a decorative mural enhances the tranquil atmosphere. Towel racks and a wooden table provide functionality.

4.96 out of 5 average rating, 49 reviews

Private Luxury Pool & Spa Retreat – Great Location

4.97 out of 5 average rating, 152 reviews

The exterior of the house features a private pool surrounded by a spacious grassy area. A wooden deck with seating is situated at the back, providing a relaxing spot to enjoy the outdoors. Lush palm trees frame the setting, creating a serene atmosphere.

Home in Pompano Beach

•Floasis• Your private FL Oasis 5 min to beach!

5 out of 5 average rating, 226 reviews

A bright sunlit dining area features a round white table surrounded by chairs, with a green plant in a pot nearby. Large glass windows overlook a pool and landscaped backyard, framed by tropical palm trees and vibrant greenery.

Villa in Pompano Beach

Oasis Waterfront! Boat Rental/Spa/BBQ/Kayaks/Pool!

5 out of 5 average rating, 135 reviews

A private patio features a heated saltwater pool surrounded by lush tropical greenery. A gazebo with comfortable seating and a gas BBQ area is showcased, alongside cozy loungers positioned for relaxation. An umbrella stands ready, providing shade over a dining area nearby.

Home in Fort Lauderdale

Curated Luxury Retreat | Pool • Spa • 8 min Beach

4.97 out of 5 average rating, 104 reviews

Home in Pompano Beach

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

Apartment in Boynton Beach

Aerial view of the Casa Costa building showcases its modern architecture and twin towers, surrounded by palm trees. The Intracoastal waterway is visible in the background, along with an expanse of greenery. The sky is partly cloudy, providing a serene backdrop.

4.92 out of 5 average rating, 189 reviews

Resort style 1BR/1BA condo

Family- and pet-friendly home rentals

A modern kitchen features sleek white cabinetry and marble countertops, equipped with premium appliances. The spacious island includes bar seating for four, illuminated by pendant lights. Natural light fills the area, emphasizing the bright and airy atmosphere.

5 out of 5 average rating, 38 reviews

Papa Steve’s Downtown Delray Beach, 3 Bedroom Pad

Superhost

The inviting exterior of the cottage is framed by lush greenery and features large windows allowing natural light to fill the interior. A hot tub is positioned in the outdoor space, accompanied by a cobblestone pathway that leads through the manicured lawn.

Cottage in Delray Beach

4.95 out of 5 average rating, 20 reviews

Turtle Tracks ~Steps to Atlantic

A spacious living room features a large, soft sectional sofa in a calming teal color. Natural light filters through a large bay window, illuminating light wooden flooring. A modern TV console is placed in front of a sleek television, enhancing the room's inviting atmosphere.

4.97 out of 5 average rating, 30 reviews

Coastal Retreat near Delray - Pet Friendly

A serene entrance pathway leads to a light blue door, framed by palm trees and tropical plants. Two turquoise chairs sit invitingly on the porch, while the surrounding landscaping features colorful foliage and well-maintained stone pavers.

4.86 out of 5 average rating, 29 reviews

Delray Beach Guest House Newly Updated!

5 out of 5 average rating, 8 reviews

Renovated Home w/ Saltwater Pool & mins to beach

A cozy living area features a comfortable sofa and a round coffee table topped with a small plant. Natural light streams in through glass doors leading to an outdoor space. The kitchen area is equipped with modern appliances, including a stainless-steel refrigerator.

4.92 out of 5 average rating, 259 reviews

Cozy Delray Beach House Waterfront Intracoastal

5 out of 5 average rating, 10 reviews

3/2 Private Home in East Delray + pool & gas grill

A private pool and spa are framed by spacious patio tiles, inviting relaxation. Lush palm trees provide shade, while a charming pergola can be seen in the background. The light-colored home features multiple sliding doors that open to the outdoor space, enhancing access to the sunlit area.

4.94 out of 5 average rating, 17 reviews

Walk to beach pool and spa home

Family-friendly home rentals with a pool

The outdoor area features a large heated pool surrounded by a spacious patio. Comfortable lounge chairs are positioned nearby, and lush palm trees add greenery to the scene. The white exterior of the house is visible in the background, with a clear blue sky overhead.

4.83 out of 5 average rating, 35 reviews

Island Estate: Pool, Tiki Lounge Near Atlantic Av

4.95 out of 5 average rating, 83 reviews

Relaxing Retreat | Pool + Near Beach & Atlantic Av

Apartment in Delray Beach

A light-colored sectional couch is positioned in a welcoming living area featuring hardwood floors. A large television mounted on the wall displays a serene beach scene. Two artworks adorn the wall beside the couch, and a stylish lamp provides soft illumination.

5 out of 5 average rating, 21 reviews

Exclusive stay in the heart of sunny Delray Beach

5 out of 5 average rating, 29 reviews

4BR Retreat w/Heated Pool • Near Downtown Delray

4.93 out of 5 average rating, 43 reviews

A bright living room features comfortable white sofas and a wooden coffee table, complemented by decorative wall art and natural accents. Soft lighting highlights the wooden ceiling and woven area rug, creating an inviting space for relaxation or gathering.

Cottage in Delray Beach

Historic cottage private pool walk to beach

A spacious outdoor area features a saltwater pool surrounded by stone tiles. A spa with multiple jets is situated beside the pool. Comfortable lounge chairs and a dining area are positioned under an overhang, with well-maintained grass and tropical plants enhancing the environment.

4.98 out of 5 average rating, 45 reviews

A quiet, relaxing, hidden oasis.

5 out of 5 average rating, 53 reviews

A light-filled living area features a comfortable sofa adorned with colorful cushions. Two windows are framed by navy blue curtains, allowing natural light to illuminate the space. A round dining table is positioned near the window, accompanied by two white chairs, creating a cozy spot for meals.

Condo in Delray Beach

Guest Favorite 3 Min Walk to Beach & Atlantic Ave

A private saltwater pool is surrounded by a spacious patio area with multiple seating options. An umbrella provides shade over a large dining table, while string lights add a subtle ambiance. Lush greenery frames the backyard, enhancing the serene outdoor setting.