Family-friendly holiday rentals in Gulf Stream

An aerial view captures the serene waterfront neighborhood, showcasing a winding waterway bordered by lush greenery and luxury homes. The proximity to the ocean is evident, with several pools and dock spaces visible among the residences.

4.97 out of 5 average rating, 101 reviews

Direct INTRACOASTAL Waterfront 3BR - Pool & Dock

Relax on your private backyard patio with the famous south Florida intracoastal waterway as your back drop. Sip cocktails & watch the million dollar yachts sail by or throw a fishing line off the dock. This is the BEST Florida home for anyone who loves waterfront living. Sunbathe in the heated pool or fire up the the outdoor kitchen grill or fire pit. Enjoying the outdoor salt life at your very own private resort is what this home is all about. No parties, events or get togethers permitted.

4.95 out of 5 average rating, 229 reviews

A serene beach scene features soft, white sand stretching along a calm shoreline. Gentle waves lap at the water's edge, transitioning from light turquoise to deeper blue. A few scattered clouds float above under a bright sky, inviting relaxation and tranquility.

Bungalow in Ocean Ridge

Bob’s Beach House Cottage Walk Steps to beach

Private Beach Cottage. 2 bedrooms and 2 bath. Large covered patio area for outdoor living. Enjoy private walks on our wonderful Beach. The beach is only 300 yards away 2 minutes walk. Next to Nomad Surf Shop you can rent Surf & paddle boards. We take pride in having the cleanest cottage in town. All tile floors, all white linens. Our cleaning service thoroughly cleans and disinfects all surfaces and linens after each occupancy. We have parking for only two cars, one’s covered under the carport.

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

4.97 out of 5 average rating, 110 reviews

A refreshing saltwater pool is framed by a spacious patio. A vibrant blue umbrella provides shade over two lounge chairs positioned partially in the water. Lush greenery and white fencing enhance the private, tranquil atmosphere of the backyard.

Home in Boynton Beach

Large Heated Pool - Family Friendly Private BBQ

Welcome to our renovated family-friendly home centrally located in the heart of Boynton Beach, Florida. This home is perfect for families seeking a spacious and friendly retreat. With 3 bedrooms, 4 beds, 2 full bathrooms, and a fully stocked kitchen and laundry area, we've ensured a relaxing and convenient stay for up to 8 people. Take a dip in our newly built saltwater HEATED pool or relaxing in the hammock's backyard, along with a bbq grill and cornhole set for you and your guests to enjoy.

4.91 out of 5 average rating, 163 reviews

A modern dining area is presented with a long table set for dinner, featuring plates, glasses, and silverware. Soft lighting is provided by an elegant pendant fixture above, while a view of the pool area and outdoor seating is visible through the sliding glass doors.

Home in Boynton Beach

Modern, spacious 4BR oasis with private pool

Feel peace + calm in this spacious, serene space. Enjoy the gentle lapping of the private pool & crickets, or fill the large, open space with laughter, family and friends. Eat indoors or out; the patio & pool are fully screened. Cool off inside without missing out; you'll still see the pool and backyard from the kitchen, dining area, living room, and master bed. The 15' couch seats all comfortably in front of the 58" 4K TV. 4 bedrooms, 2 baths. Quiet, residential home. Best for low-key stays.

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, 240 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 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.

4.94 out of 5 average rating, 269 reviews

Peaceful 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 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!

4.98 out of 5 average rating, 108 reviews

A private tropical backyard features a heated salt system pool surrounded by lush greenery. Loungers are positioned beside the pool, and a red umbrella provides shade over a designated seating area. The home’s windows offer views into the tranquil outdoor space.

Home in Boynton Beach

Jungle Heated Salt Pool, Private, Near Beach

Welcome to the Jungle House – Your Private Salt Pool Oasis Unwind in your own tropical retreat just 5 minutes from the ocean. Hidden in a quiet Boynton Beach neighborhood, this 3-bedroom, 2-bath family-friendly home blends safari-inspired design with lush jungle gardens and a heated saltwater pool you’ll never want to leave. Whether you’re relaxing under the trees, grilling dinner by the pool, or biking to the beach, the Jungle House offers the perfect mix of adventure and privacy.

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.

4.91 out of 5 average rating, 158 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!

4.79 out of 5 average rating, 275 reviews

Cottage in Delray Beach

Oasis on the water, Delray

Enjoy the screened in Florida room with beautiful new hurricane proof sliding doors Wake up to coffee on the dock, the tropical birds singing, and watch the tide roll in and out. Watch the manatees roll around with their young. Enjoy a paddle with two free shared kayaks. Welcome to Delray’s best kept secret This 85 year old cottage on the water has more character than you can imagine. While it has had some upgrades, it’s not perfect but has so much to offer!

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, 119 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.