Family-friendly holiday rentals in Delray Beach

4.91 out of 5 average rating, 163 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

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.

4.94 out of 5 average rating, 239 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.

4.92 out of 5 average rating, 220 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.

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, 157 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!

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, 146 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

4.99 out of 5 average rating, 115 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.

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.

4.97 out of 5 average rating, 117 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.

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 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.

4.87 out of 5 average rating, 269 reviews

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!

4.95 out of 5 average rating, 165 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.

A private outdoor space features a sparkling swimming pool surrounded by lounge chairs and dining table. A large pink flamingo float rests in the water, while vibrant flowers frame the scene, adding color to the patio area.

4.9 out of 5 average rating, 261 reviews

Lux 2 King beds 4 Br2 bath, walk to everything.

Professional Hospitality, sparkly clean, luxurious finishes, organic cotton & down beddings. Teak furniture and a relaxing tub. Relaxing outdoor patio and dining. Only 2 walking blocks from the vibrant Atlantic Ave and shuttle to the beach (no need to drive anywhere!!!). Great for families or a group. No Pets no exception. ABSOLUTELY NO SMOKING- INDOOR and OUTDOORS. **If you are a smoker, kindly, DO NOT consider staying here.

An expansive heated pool is illuminated in a calming blue, reflecting the surrounding tropical landscaping. A thatched-roof Tiki Hut provides shaded seating, while loungers line the poolside. A glass-walled indoor area offers additional space for relaxation and dining.

4.91 out of 5 average rating, 104 reviews

TROPICAL ISLAND INSPIRED POOL HOME NEAR THE BEACH

Submerge yourself into your own private resort style home with a Tiki Hut on the edge of an oversized heated pool, surrounded by lush tropical landscaping, outdoor and indoor dining and living areas. Stylish Interior with a feel of Bahamian islands with a hint of safari. The home is perfectly situated within a 2 mile radius from the beach, shopping, dining, and the nightlife entertainment Delray Beach has to offer.

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

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.

4.98 out of 5 average rating, 106 reviews

Paradise Palms our tropical oasis in Delray/Boca!

4.84 out of 5 average rating, 274 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, 151 reviews

Home in Boca Raton

Luxury 3brm lakehouse. Pool, Tiki , golf & Fishing

5.0 out of 5 average rating, 149 reviews

A spacious pool area is presented, featuring a rectangular pool surrounded by lounge chairs and tropical landscaping. A thatched-roof gazebo offers a shaded seating area in the background, while a large umbrella provides additional shade near the pool. The bright blue sky enhances the inviting atmosphere.

Home in West Palm Beach

Jungle Oasis with Heated Pool, Tiki Hut & Hot Tub

4.97 out of 5 average rating, 155 reviews

A cozy living area features a light-colored sofa and two yellow accent chairs, arranged around a wooden coffee table. A large flat-screen television is mounted on the wall, and natural light enters through the windows, illuminating the wood-beamed ceiling and enhancing the spaciousness.

Cottage in Boynton Beach

The Palm Bay Cottage Getaway

4.95 out of 5 average rating, 111 reviews

The Goodtime House - Heated Pool+Hot Tub Sleeps 10

4.96 out of 5 average rating, 164 reviews

A vibrant outdoor space features a large palm tree amidst well-manicured grass and tropical plants. Cozy seating with string lights creates a relaxing evening ambiance. Pathway stones lead toward a putting green area, enhancing the backyard's recreational appeal.

Home in West Palm Beach

“The Palms” Tropical Oasis|Beach|Scuba|Downtown

4.8 out of 5 average rating, 167 reviews

A serene backyard scene features two lounge chairs positioned near a sparkling pool. Soft lighting surrounds the area, casting a warm glow on the patio and nearby seating. Lush greenery and a clear sky enhance the tranquil atmosphere.

Home in Lake Worth

Canal-1 3/2 Beach Style House with Heated Pool

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 155 reviews

A vibrant pink pool float with the text 'OUT OF OFFICE' is placed in the clear blue water of a private swimming pool. Additional pool floats in various colors are visible, creating a playful atmosphere. Lush greenery surrounds the pool area.

Home in Lake Worth

Tranquil Vibes ~ Pet Friendly Private Pool Home

5.0 out of 5 average rating, 101 reviews

The exterior of a charming cottage is depicted, showcasing light blue siding complemented by a white porch and vibrant green landscaping. A blue awning shades a window, while colorful plants and a well-manicured lawn invite relaxation. Soft natural light illuminates the scene.

Cottage in Delray Beach

Gated Beach Cottage, walk to town, dog friendly.

Apartment in Delray Beach

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.

Charming carriage house!

4.95 out of 5 average rating, 148 reviews

4.92 out of 5 average rating, 105 reviews

A welcoming exterior of a single-story home is featured, with a brick driveway curving toward a double garage. Lush greenery and palm trees frame the space, enhancing the inviting atmosphere. The clear blue sky adds to the tranquil setting, highlighting the home's charming architecture.

Home in Boca Raton

Beachside 4 Bedroom home with large pool

Luxe

A clear view of the heated outdoor pool is presented, featuring built-in loungers on one side. The spacious patio is bordered by vibrant tropical landscaping and includes multiple seating areas. The white home is visible in the background, along with a second-floor balcony.

5.0 out of 5 average rating, 37 reviews

210 Walk to Pineapple Grove | by Brampton Park

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.

4.99 out of 5 average rating, 85 reviews

The Vacation Getaway with a Heated Salt Water Pool

5.0 out of 5 average rating, 71 reviews

Condo in Delray Beach

Delray Beach Escape | Walk to Beach + Atlantic Ave

5.0 out of 5 average rating, 58 reviews

Family-friendly home rentals with a pool

4.88 out of 5 average rating, 251 reviews

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.

Condo in Delray Beach

Charming studio just by the beach & Atlantic Ave

4.81 out of 5 average rating, 47 reviews

Heated Pool • Putting Green • 5 Min to Beach

4.93 out of 5 average rating, 27 reviews

Gorgeous Modern Beach Heated Pool House Sleeps 8

5.0 out of 5 average rating, 51 reviews

4BR Retreat w/Heated Pool • Near Downtown Delray

Townhouse in Delray Beach

SWiSS LiViNG - Lakeside Haven | Pool & Gym

5.0 out of 5 average rating, 15 reviews

An outdoor space is presented, featuring a pool surrounded by paver stones and tropical landscaping. Several lounge chairs are positioned poolside, alongside a dining area set with a table and chairs. A fenced yard is visible in the background, providing privacy.

4.95 out of 5 average rating, 40 reviews

Paradise in the Palms

4.86 out of 5 average rating, 50 reviews

An outdoor patio area is furnished with comfortable seating and a swing chair, surrounded by palm trees and lush greenery. The space is inviting with soft lighting and offers views of the waterway, enhancing the serene atmosphere during twilight.

Villa in Delray Beach

Hidden Harbor Paradise -Private Heated Pool w/Dock