Family-friendly holiday rentals in Delray Beach

4.9 out of 5 average rating, 225 reviews

Lux King bed 2br 1bath, walk to everything #309

Professionally managed and cleaned, luxurious finishes, organic cotton and down beddings, teak furniture and chefs' ready kitchen. Relaxing shared outdoor area, free laundry machine, outdoor shower and dinner table. Conveniently located within 2.5 walking blocks from the vibrant Atlantic Ave resutarants and shuttle to the beach (no need to drive). 2 Identical units always full in season. ABSOLUTELY NO SMOKING- INDOOR and OUTDOORS. **If you are a smoker, kindly, DO NOT consider staying here.

Guest house 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, 221 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!

Guest suite in Delray Beach

A bright living room is featured, showcasing a blue sofa with pillows and a natural landscape art piece above it. A round dining table with white chairs is visible, along with a small plant and a coffee table. Natural light enters through a glass door.

4.88 out of 5 average rating, 103 reviews

Blue Ocean - 1 Bedroom Apt/ Near the Beach

Unique 1 bedroom apartment with a full living room and kitchen. Located in a calm neighborhood walking distance to the beach (~0.7 miles) and a mile from downtown. Experience the nightlife or spend your days relaxing at the beach and come home to this comfy, private apartment. Also located within a few blocks of the following; the oldest bar in Delray, a delightful French Bakery, a 24 hour convenience store, a barber, a dentist, consignment shops, a grocery store, and the intracoastal waterway.

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.

4.94 out of 5 average rating, 140 reviews

Heated Pool | King Bd | Cozy Backyard | Quiet Stay

WORLD CUP 2026 Destination 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

4.91 out of 5 average rating, 161 reviews

Family & Pet Friendly NEAR Beach/AtlanticAve/FAU

Central Location - Quick drive to the beach! ▪️5 min. drive (1.8 miles) to the Beach ▪️3 min. drive (3/4 mile) to Downtown Delray - Restaurants, shops, bars and night life ▪️5 min. drive to the nearest grocery store - Publix, Bedner's Farm Fresh Market ▪️7 min. drive (2.7 miles) to Target/Trader Joe's ▪️2 min. drive to the Historic Swinton Ave ▪️2 min. drive to the Delray Tennis Center ▪️20 min. drive (18 miles) to West Palm Beach Airport ▪️35 min. drive (32 miles) to Fort Lauderdale Airport

An outdoor seating area under a thatched roof features comfortable lounge furniture arranged around a gas fire table. A flat-screen TV is mounted nearby. The inviting pool is visible in the background, surrounded by tropical landscaping and sun loungers.

4.99 out of 5 average rating, 101 reviews

Paradise Palms our tropical oasis in Delray/Boca!

Welcome to Paradise Palms, our tropical oasis! This 3 bedroom, 2 bath home is a perfect getaway to relax and unwind. Enjoy the beautiful pool, hot tub, and tiki hut with gas fire table, bar and TV. There is a wood fire pit, hammock, 4 bikes, 4 beach chairs, snorkeling gear, ping pong and plenty of outdoor games. The interior has all of the comforts of home with a fully equipped kitchen, TV in every room. The property is conveniently located near the beach, downtown Delray, and Boca Raton.

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, 224 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.

The charming exterior of the cottage is framed by lush greenery and palm trees, with sunlight filtering through the leaves. A spacious front yard features a hammock and pathways lined with white stones, enhancing the inviting atmosphere of the property.

4.93 out of 5 average rating, 202 reviews

CASA SWINTON – 226 S. Swinton Avenue

South Florida Paradise found! Casa Swinton is a pristine, award-winning, 3-Bedroom, 2.5 Bath, 1942-built Cottage in East Delray Beach, minutes walking distance from Delray Beach’s famous Atlantic Avenue. Completely Renovated with exquisite Charm and Class. Sleeps 8 guests with endless lounge areas to relax and enjoy in privacy. 2 short Blocks from Delray’s Atlantic Avenue and Tennis Center. Walking Distance to the Beach, Over 150+ Restaurants, cozy Boutiques, Shoppes and much more.

Apartment in Delray Beach

A sandy path leads to the beach, bordered by lush green vegetation on either side. Wooden posts with ropes define the walkway, which opens up to a view of the blue sky and the distant ocean, creating an inviting coastal atmosphere.

4.87 out of 5 average rating, 237 reviews

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.

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, 104 reviews

The Dream Delray/ 4 BR En-suite Pool Home

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.

Guest house 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.

4.87 out of 5 average rating, 253 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.

4.95 out of 5 average rating, 147 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.

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

Superhost

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, 122 reviews

Delray Bali House ~ Heated Pool ~ Sauna ~ Hot Tub

4.93 out of 5 average rating, 230 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

4.97 out of 5 average rating, 159 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!

4.81 out of 5 average rating, 191 reviews

The pool area features a heated saltwater pool, surrounded by a secure child fence. Clear blue water glistens under the sun, while a spacious deck offers a tranquil space for relaxation. The area is framed by palm trees and a well-maintained green landscape.

Home in Boca Raton

1mi to Beach 2 Suite 4bd/3bth Home with Pool &Spa

4.83 out of 5 average rating, 237 reviews

A hot tub is positioned alongside a tranquil body of water, with clear blue water bubbling within. Two glasses are set beside a bottle of wine on the edge. Lush greenery and a fence frame the background, contributing to a serene outdoor environment.

Home in Boynton Beach

Beautiful house with jacuzzi and pool table!

4.93 out of 5 average rating, 114 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

4.99 out of 5 average rating, 118 reviews

An expansive view of the waterfront mansion at dusk, with a private dock accommodating a boat. The illuminated pool reflects the surrounding palm trees and twinkling lights from nearby homes. A serene waterway stretches into the distance, framed by lush greenery.

Home in Pompano Beach

Luxurious waterfront mansion - large heated pool

Superhost

The outdoor area features a heated saltwater pool and spa, surrounded by a screen enclosure. Soft lighting illuminates the space, with a large sailfish decoration hanging overhead. A lantern and a small table on the side enhance the ambiance, while lounge chairs provide relaxation options.

4.88 out of 5 average rating, 69 reviews

Sailfish Cove –Tropical Escape Minutes from Delray

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, 42 reviews

Papa Steve’s Downtown Delray Beach, 3 Bedroom Pad

4.99 out of 5 average rating, 110 reviews

Cottage in Delray Beach

Happy Mango | Heated Pool | Walk to Atlantic Ave

A bright and airy open-concept living space features light-colored wood flooring and modern furnishings. The dining area showcases a white table surrounded by woven chairs. A spacious kitchen can be seen in the background, with sleek cabinetry and a large island. Natural light pours in through multiple windows.

5 out of 5 average rating, 22 reviews

Stunning 3 BED modern pool home by the Beach

Townhouse in Delray Beach

A bright and airy living space is highlighted by large windows allowing natural light, complemented by modern furnishings. A dining area features a sleek table with comfortable chairs, while a cozy sofa invites relaxation. The stylish decor adds a fresh touch to the space.

4.98 out of 5 average rating, 41 reviews

Casita Charming

4.95 out of 5 average rating, 146 reviews

The exterior of the apartment features a charming brick pathway leading to a white building surrounded by lush palms and vibrant flowers. A well-maintained garden area and seating provide a welcoming entry. The clear blue sky adds a bright backdrop to the scene.

Flat in Delray Beach

Charming carriage house!

Apartment in Delray Beach

4.87 out of 5 average rating, 167 reviews

Best Kept Atlantic Avenue Secret. Fab Location!!!

5 out of 5 average rating, 50 reviews

* Modern Oasis w/ Private Yard, Pool, Full Kitchen

4.83 out of 5 average rating, 23 reviews

A charming duplex with a light yellow exterior is framed by two palm trees and lush green shrubs. The front features two windows with blue shutters, while a wooden fence provides privacy. The pathway leads to a welcoming entrance set amidst a tropical landscape.

Flat in Delray Beach

Tropical Duplex with Pool

Family-friendly home rentals with a pool

A modern kitchen features a spacious island with four wooden stools. White cabinetry is paired with a marble countertop and hexagonal tile backsplash. Stainless steel appliances, including a gas stove and a dishwasher, are visible, along with open shelves displaying decorative items.

4.97 out of 5 average rating, 66 reviews

Gorgeous 3 bed/3 bath single family home

A living area features large windows that provide views of the waterfront and lush greenery. Comfortable seating is arranged around a coffee table, with decorative pillows adding texture. A flat-screen TV sits on a media console, with a ceiling fan overhead contributing to the airy atmosphere.

4.96 out of 5 average rating, 24 reviews

Waterfront 3BR! Spacious Dock, King Bed, BBQ

4.96 out of 5 average rating, 92 reviews

Sunny Pool Escape • Fire Pit • 10 mins to Atlantic

An outdoor covered patio features seating arrangements with comfortable furniture, complemented by decorative cushions. A fan hangs from the wooden ceiling, providing a cooling breeze. The lush backyard offers views of a large heated pool surrounded by tropical landscaping.

4.93 out of 5 average rating, 123 reviews

Heated Pool! 1 Mile To Beach & Atlantic Avenue!

5 out of 5 average rating, 14 reviews

Renovated Home w/ Saltwater Pool & mins to beach

5 out of 5 average rating, 29 reviews

Lucky Day: Designer Home, Arcade, Park, Htd Pool

A serene outdoor space features a heated salt-water pool and a Jacuzzi. Vibrant LED lights illuminate the clear water, surrounded by lush tropical landscaping and palm trees. Comfortable lounge chairs invite relaxation, while the tranquil ambiance is enhanced by soft evening light.

4.97 out of 5 average rating, 99 reviews

Htd Pool/Spa, Putt Green & G. Tee- Walk to The 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.