Family-friendly holiday rentals in Delray Beach

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

Family · Indoor spaces · TV

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.

Indoor spaces · Family · Location

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.

Kitchen · Indoor spaces · Outdoor spaces

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!

Family · Kitchen · Decor

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.

Kitchen · Indoor spaces · Amenities

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.

Kitchen · Indoor spaces · Air conditioning

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.

Kitchen · Family · Cleanliness

Best Location Ever! Comfy, Cozy & Clean 2bd/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!

Family · Indoor spaces · Check-in

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 spaces · Family · Comfort

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.

Indoor spaces · Family · Hot tub

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.

Kitchen · Indoor spaces · Bathroom

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!

Family · Indoor spaces · Parking