Family-friendly holiday rentals in Delray Beach

5 out of 5 average rating, 110 reviews

A spacious outdoor area features a heated, screened-in pool with colorful inflatable toys. Nearby, a well-maintained game area includes artificial turf and classic games. The contemporary kitchen showcases stainless steel appliances and a large island with seating, while the living room enjoys natural light and comfortable seating.

Home in Deerfield Beach

Luxe 3-Bedroom Vacation Home|Pool|Blocks to Beach

JUST ACHIEVED COVETED TOP 1 % of all AIRBB Properties. Enjoy a magical beach vacation at this new-renovated, single-story home. Indulge in evening cocktails under the covered patio and enjoy a screened in, heated pool – completely pest-free! Inside, find a stylish living room, a modern kitchen, and three lovely bedrooms. Room for the whole family plus a MILE to the beach.Large Capacity Washer & Dryer 4 Min Drive to Island Water Sports 5 Min Drive to Beach 7 Min Drive to Mizner Park High Repeats

Guest suite in Pompano Beach

A bright bedroom features a spacious bed with a decorative pillow and light bedding. Two windows with sheer curtains allow natural light to fill the room. Bedside tables are placed on either side of the bed, and a ceiling fan adds a refreshing touch.

4.91 out of 5 average rating, 334 reviews

Totally Private Studio, NO shared Spaces-Renovated

Luxurious Private Studio w/ Private Entrance (440 sq ft- can fit 3 people/2 cars) is attached to our home & 1.7 miles from beach & adjacent to Ft Lauderdale. Park under the covered carport. 1 Queen Bed (& 1 Queen Size-Blow Up Mattress), 1 Bath, Kitchenette, Fiber Optic Wifi, Flat Screen TV (140 channels), Impact Windows, Huge Closet, Fan/light, AC w/ remote, Desk, Chair, fold up/down Table for eating w/ chairs, small Fridge, Microwave, Toaster Oven, Foreman Grill, Hot Plate Stove, Coffee Maker.

4.85 out of 5 average rating, 254 reviews

A serene outdoor space featuring a heated pool surrounded by palm trees and lounge chairs. A wooden dock extends into the intracoastal waterway, providing a picturesque view. The patio area includes shaded seating arrangements, creating an inviting setting for relaxation.

Condo in Pompano Beach

ON CANAL! Pool+Walk to BEACH! Boat Watch! 1b/1b

Beautiful 1 bedroom condo located directly on the intracoastal with a heated pool. This unit DOES NOT have water view from the condo BUT has amazing views of the intracoastal waterway from the patio/pool area. Enjoy watching the yachts sail by along with taking in amazing sunsets from the dock. Work from home, 1 block from the beach! Quiet and peaceful. Within walking distance to many shops and local amenities! Perfect for couples, young families and groups of friends traveling together.

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.

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.

4.93 out of 5 average rating, 242 reviews

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 feet 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!

Guest suite in Lake Worth

4.95 out of 5 average rating, 292 reviews

Tropical Oasis Guesthouse w/ private entrance

Cozy, private getaway in Lantana, which is owner occupied. French doors open to a tropical paradise. Just 10 minutes from airport, beaches, restaurants, convention center & shopping. Enjoy the sounds of nature on your private deck secluded by palm trees. Includes A/C, bathroom, Smart TV and parking. NOTE: Does not have a full kitchen, however, it includes a sink, refrigerator, microwave, hot plate, and utensils for fixing simple meals w/plenty of counter space! (see photos) NO STOVE

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.

4.94 out of 5 average rating, 110 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!

4.96 out of 5 average rating, 222 reviews

A row of blue beach chairs with matching umbrellas is set up on a sandy beach, providing shade against the sun. The calm ocean waters can be seen in the background, with a clear sky filled with soft clouds overhead.

Cottage in Delray Beach

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

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, 196 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.

4.87 out of 5 average rating, 223 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

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.

A spacious living area features natural wood beams overhead and large windows allowing natural light to fill the space. A comfortable sectional sofa with colorful cushions is positioned next to a modern coffee table. A dining table is visible, accompanied by mid-century style chairs.

4.82 out of 5 average rating, 108 reviews

2 Bed Cottage walk to Pineapple Grove Ave & Beach

Keep it simple at this peaceful and centrally-located place. This remodeled cottage features a brand new kitchen and bathroom. Spend your days either relaxing in the quiet patio surrounded by greenery or walk to Pineapple Grove or the Ave for a drink or bite to eat. Enjoy time at the beach with your friends and family and in the evening take a stroll through the historic district soaking in the real culture of Delray Beach.

4.99 out of 5 average rating, 100 reviews

Cottage in Delray Beach

Private Pool Cottage | Fast WI-FI -Walk to the Ave

November is one of the most peaceful times to enjoy Delray Beach—warm days, quiet beaches, and no crowds on The Avenue. Escape to The Happy Mango Hideaway, your private cottage with a heated saltwater pool, fast Wi-Fi, and spa-style bath (renovated Oct 2025). Whether working remotely or winding down, enjoy open living, full kitchen, and a cozy workspace. Walk to Atlantic Ave or unwind in your fenced tropical oasis.

Popular amenities for Delray Beach family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 135 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!

Home in Poinsettia Heights

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.

5 out of 5 average rating, 115 reviews

Casa Déjàvu 5*spot Heated pool /HotTub /8min Beach

4.82 out of 5 average rating, 202 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!

Guesthouse in Flamingo Park

A bright bedroom features a spacious bed with a textured white cover. Soft blue pillows are arranged neatly, and a cozy chair is placed beside a vintage-style trunk. Natural light enters through two large windows, complemented by light green blinds, creating an inviting atmosphere.

4.98 out of 5 average rating, 470 reviews

Key West Style Suite with Pool/Spa

4.93 out of 5 average rating, 101 reviews

A spacious Jacuzzi is illuminated with soft blue lights, situated on a paved area overlooking the serene water. Palm trees are visible nearby, and distant properties are softly glowing along the waterfront, creating a calming nighttime ambiance.

Home in Imperial Point

Paradise Waterfront-Jacuzzi-heated Pool-familyhome

4.89 out of 5 average rating, 122 reviews

The outdoor space features a well-manicured lawn with a putting green, framed by lush greenery and palm trees. Soft lighting enhances the atmosphere as the sunset casts a warm glow over the two-story home, creating a welcoming environment for outdoor activities.

Home in Lake Worth

Drift Inn- Lakefront! Outdoor Bar, Golf, sleeps 14

4.97 out of 5 average rating, 170 reviews

A wooden hot tub is surrounded by a multi-tiered deck on lush green grass, set against a vibrant sunset sky. A barrel sauna is visible nearby, with soft lighting creating a cozy ambiance, while tropical plants add touch of nature to the serene outdoor space.

Home in West Palm Beach

Bio Hacker Resort! Pool, Sauna, ColdPlunge, HotTub

4.89 out of 5 average rating, 154 reviews

A rooftop terrace features several white lounge chairs arranged around a geometric patterned floor. Sun loungers are positioned under shaded cabanas, with umbrellas providing additional coverage. The backdrop includes a stunning view of the horizon under a colorful sky at sunset.

Condo in Central Beach

W Residences - Beachfront 2 bedroom oasis

Family- and pet-friendly home rentals

Cottage in Lake Worth Beach

A vibrant outdoor space is surrounded by palm trees and lush plants, featuring a splash pool and a hammock. Soft grass covers the ground, leading to a charming cottage with a welcoming red door visible in the background.

4.99 out of 5 average rating, 146 reviews

Private & Pet Friendly, Key West-King Bed Cottage

4.94 out of 5 average rating, 107 reviews

A spacious living area features a large light gray sectional sofa facing a mounted television, with a wooden media console below. A ceiling fan is visible above, while natural light floods in from large windows leading to the dining area, which includes a wooden table and chairs.

Home in Boca Raton

Private Oasis with Heated Pool close to the Beach

A tropical backyard is showcased, featuring a kidney-shaped pool surrounded by palm trees and lounge chairs. A nearby deck area includes a dining table under a vibrant red umbrella. The bungalow's exterior is visible in the background, completing the serene outdoor setting.

4.91 out of 5 average rating, 211 reviews

Grab Flip Flops & Wine Glasses ✦ RELAX ✦ Welcome!

A thoughtfully designed sleeping area features a spacious bed with crisp white linens and rolled towels at the foot. A light-colored table and chairs provide a cozy dining space. The kitchen area showcases bright blue cabinetry and modern appliances, with natural light streaming through the window.

4.92 out of 5 average rating, 219 reviews

the writer's nook • treehouse economical studio

Guesthouse in Delray Beach

The renovated cottage features a light pink exterior with white shutters and a welcoming door. A covered entryway is visible, surrounded by lush greenery. Two lounge chairs are positioned on a paved patio area, providing a space for relaxation outdoors.

4.85 out of 5 average rating, 179 reviews

Private cottage two blocks to Atlantic Ave.

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.

4.96 out of 5 average rating, 142 reviews

Charming carriage house!

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 out of 5 average rating, 23 reviews

210 Walk to Pineapple Grove | by Brampton Park

4.88 out of 5 average rating, 173 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

Family-friendly home rentals with a pool

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.

4.91 out of 5 average rating, 233 reviews

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

5 out of 5 average rating, 5 reviews

Luxury Tropical Oasis I By Hotel Home Stays

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, 93 reviews

The Dream Delray/ 4 BR En-suite Pool Home

4.89 out of 5 average rating, 94 reviews

A balcony overlooks a lush landscape featuring tall palm trees and a calm body of water. The background includes modern buildings against a clear sky, creating a serene view from the outdoor space.

Condo in Boynton Beach

Walk to the beach! Lovely one bedroom with pool.

A collage showcases various aspects of the property, including a pristine beach with lounge chairs, lush garden greenery, a cozy living area with seating, and a vibrant pool surrounded by sun loungers and palm trees, encapsulating an inviting seaside experience.

4.8 out of 5 average rating, 138 reviews

Beach Studio Steps from Ocean & Atlantic Ave

Tiny home in West Palm Beach

A modern container home is highlighted, featuring a sleek wooden facade and large glass doors. A stone pathway leads to the entrance, surrounded by lush green grass. The outdoor area includes a small deck nearby, offering additional space for relaxation.

4.95 out of 5 average rating, 55 reviews

BoxHaus Modern tiny home in the heart of WPB

A serene heated pool is surrounded by lounge chairs and umbrellas, set against a backdrop of lush palm trees. The scene is illuminated by the warm colors of a sunset sky, creating a tranquil outdoor living space.

4.98 out of 5 average rating, 54 reviews

312 Delray Retreat: Pool, Tiki Hut & Putting Green

A spacious shared pool is highlighted, surrounded by lush palm trees and lounge chairs. A cabana provides a shaded area for relaxation. The clear water of the pool reflects the blue sky, offering a serene space for guests to unwind.