Family-friendly holiday rentals in Delray Beach

Delray Holiday Escape • Heated Pool • Walk to Ave

Escape the winter chill and celebrate the holidays 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.

Spacious Designer Home Htd Pool Near Atlantic Ave

Step into the luxe and spacious 4BR 2.5BA oasis in the heart of Delray Beach, FL. It promises a relaxing retreat just a few minutes from bustling Atlantic Ave, sunny beaches, restaurants, shops, exciting attractions, and landmarks. The unique designer ambiance and rich amenity list will leave you in awe. ✔ 4 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Backyard (Heated Pool, Fire Pit, BBQ, Lounges) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry ✔ Parking Learn more below!

Dockside Nautical Fishing Cottage. Intracoastal!

Wake up to coffee on the dock, the tropical birds singing, and watch the tide roll in with all the sea life that moves in with it. Watch the manatees roll around with their young, take in the Eastern exposure with the bright sun on the dock all day and in the screened area This unit sleeps 2 and provides the shared use of two kayaks, with the guest in the other unit. Welcome to tranquility Enjoy the newly renovated screened in Florida room with beautiful new hurricane proof sliding doors

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.

CASITA DELRAY (314 SW 2nd Street)

Charming Renovated 2 Bedroom “Casita” Close to Downtown Delray Beach!! Beautifully Decorated with thoughtful details throughout Quality Mattresses, Bedding, Plush Pillows,, & Towels, 2 Beach Cruiser Bicycles for a quick ride downtown or to the beach 3 Beach Chairs / Beach Umbrella / Beach Towels / Yoga Mat Provided Private Fenced Backyard with Weber BBQ / Table and Chairs for Outdoor Dining / Hammock. Close to Downtown....Restaurants, Bars, Shoppes, Nightlife and award-winning BEACHES ;)

Cozy Delray Beach House Waterfront Intracoastal

🏝LOCATION, LOCATION, LOCATION! Delray Beach's BEAUTIFUL waterfront property! The Bamboo Beach House is located directly on Intracoastal waterway in Delray Beach. Each unit has private patio overlooking 40 ft of waterfront! Enjoy morning coffee and experience beautiful sunrises with the ocean breeze. Our piece of waterfront is a favorite area of local manatees to swim in with the tides, along with schools of jumping fish! The amazing water views and aquatic wildlife is second to none!

Lux King bed 2br 1bath, walk to everything #307

Professional hospitality, always sparkly clean, tropical vibes, luxurious finishes, organic cotton and down beddings. Teak furniture and chefs' kitchen. Relaxing shared outdoor area with an outdoor shower. Only 3 walking blocks from the vibrant Atlantic Ave and shuttle to the beach (no need to drive anywhere!!!). 2 matching units 2BR each. Book in advance- always full in season. ABSOLUTELY NO SMOKING- INDOOR and OUTDOORS. ** If you are a smoker, kindly, DO NOT consider staying here.

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!

Beach Retreat W/Cabana Service | Steps to Downtown

Welcome to your retreat filled with sun & fun, where you can relax in the tropic air and aqua blue waters of Delray Beach. You will enjoy our well-appointed, newly renovated guest house originally built in 1929 & located in historic downtown Delray. Live like locals as you enjoy a bike ride or an evening stroll to our lively downtown and beautiful beaches. With our amenities and superb level of cleanliness, you will experience a level of comfort unmatched by hotels or other Airbnbs

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 poet's pad treehouse vibes with cool design

With its treehouse ambiance, the Orange Door Suite contrastingly features a boldly updated kitchen. All new stainless steel appliances, quartz countertops, and a newly renovated bath, this unit boasts a quirky, luxurious, and modern interior. The large windows let in loads of natural sunlight, and a glimpse of picturesque views of the trees. The outdoor scapes will remind you of a dreamy Key West bungalow!

Retreat | Work-ready, Parking, WiFi, Near Beach

Beneath a mango tree, your tropical home base awaits. 🌴 Casa Gonzo blends South Florida sunshine with cozy comfort—reliable high-speed Wi-Fi, full kitchen, laundry, and 24/7 self check-in. Well suited for work trips ⚡, clinical rotations 🩺, family visits, or last-minute stays—just ~6 minutes from the beach. Same-day bookings + instant access!