Family-friendly vacation rentals in Gulf Stream

Apartment in Boynton Beach

A modern living area is showcased, featuring two dark gray sofas and a striped accent chair. A circular coffee table sits in the center, surrounded by palm-themed artwork. A ceiling fan provides comfort, while a decorative light fixture hangs in the distance.

4.85 out of 5 average rating, 135 reviews

Oasis in Ocean Ridge, Walk to Beach

Welcome to your new Beach House! Completely renovated 3 Bedroom, 1 Bathroom Home located directly on A1A. Styled to bring the Ocean to your mind, body & soul. Just walking distance to one of most beautiful Beaches in South Florida! 2 minute walk to Nomads Surf Shop for all your surfing/beach needs! 10 minutes away from the Famous & Exciting Downtown Delray for shopping & fine dining or a night out in a beautiful town. So much to see! Have a large family/group? There is 2 more units you can rent

4.81 out of 5 average rating, 188 reviews

A landscaped yard features lush palm trees and tropical plants, creating a serene outdoor space. A stone pathway winds through the grass, leading to a small seating area with a round table and chairs, set under the shade of the trees.

Home in Boynton Beach

House by the beach in a secluded area

Completely private,Recently remodeled and tastefully furnished in true Florida fashion. Kid and pet friendly with plenty outdoor space with private above ground pool, located less than 5 minutes from the beach. Walkable distance to local shops, restaurants and entertainment. The house has NO cameras inside. We have a ADT alarm system in the living room that has a motion sensor for when the alarm is set on away mode. (If guest want to use it the alarm). We only have cameras outside of the house

Apartment in Delray Beach

The image captures a serene view of a canal bordered by lush greenery and palm trees. A private dock with patio chairs and a table extends over calm waters, where various boats are moored. The setting highlights a peaceful outdoor space, perfect for relaxation.

4.73 out of 5 average rating, 262 reviews

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

Top guest favorite

A cozy living area features a leather sofa adorned with striped pillows and a textured throw. The walls display a curated selection of art, while a brightly colored accent wall delineates a doorway, leading to the bedroom beyond with soft lighting and neutral-colored bedding.

Home in Boynton Beach

4.96 out of 5 average rating, 178 reviews

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

Beneath a mango tree, your tropical home base awaits. Casa Gonzo is where sunshine meets cozy simplicity—fast Wi-Fi, full kitchen, laundry, and self check-in 24/7. Perfect for work trips, family visits, or last-minute getaways. Walk to dining and local gems, or drive 6 minutes to the beach. Stay for the vibe! 🌴 Your soft landing awaits. Perfect for: Visiting family & holiday overflow stays ⚡ Work crews, contractors, on-the-go pros. 🩺 Clinical rotations. Same-day bookings + instant access!

A bright living area is furnished with a light-colored sofa and two wicker chairs, each with decorative cushions. A rectangular coffee table is centered on a soft area rug. Natural light fills the space through large windows, and a wall-mounted TV is positioned across from the seating arrangement.

4.95 out of 5 average rating, 235 reviews

Peaceful & Roomy Waterfront Delray Beach House

🏝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!

Top guest favorite

Guest suite in Lake Worth

4.94 out of 5 average rating, 289 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 spacious living area is defined by a high, wooden ceiling and neutral tones. A white sofa is positioned against a textured brick wall, accompanied by a round dining table and blue chairs. A large window allows natural light, complemented by a vibrant piece of artwork and decorative elements.

4.86 out of 5 average rating, 138 reviews

2 BD Delray Beach Cottage walk to The Ave & beach

Your friends and family will be close to everything when you stay at this centrally-located trendy apartment in the Historic District of Delray Beach. This newly remodeled mid-century modern apt features a brand new kitchen where guests can gather and cook up their favorite meals. Spend your days tanning and swimming at the beach before relaxing in your private patio for an afternoon drink then walk over to Pineapple Grove and "the Ave" for live music, great food, dancing, and fun!

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, 106 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!

A hot tub with bubbling water is surrounded by lush greenery and palm trees. A shaded area above the tub offers protection from the sun. A pathway is visible in the background, lined with tropical plants, contributing to a serene outdoor space.

4.74 out of 5 average rating, 127 reviews

The Captains Quarters of Delray Beach

Come relax in this comfortable Delray Beach getaway. Spacious clean home with outdoor kitchen, sun deck and hot tub. Good vibes decorated in cherry wood mahogany. Open kitchen for entertaining large couch with Wi-Fi and cable. Three nice size bedrooms and beautiful dining room, 6 seating marble table. Great neighborhood centered in town 5 min to the beach, downtown delray, marinas, shopping, 15 min to PBI airport. House is offered by a Florida local knowledged boat captain. RELAX.

A spacious pool area is surrounded by a well-maintained yard, featuring vibrant green foliage. Two blue umbrellas provide shade over a dining table set for six, while four lounge chairs await sunbathers. A whimsical flamingo float is resting on the water, adding a playful touch.

4.93 out of 5 average rating, 146 reviews

DWTN Delray Pool Home | FREE Beach Cabana service

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!

4.87 out of 5 average rating, 220 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.

An open-concept kitchen and dining area features modern stainless steel appliances and a spacious island with seating. Natural light floods the room through large sliding glass doors, which lead to an outdoor patio. Minimalistic decor includes potted plants on the dining table.