Family-friendly holiday rentals in Gulf Stream

4.95 out of 5 average rating, 228 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.

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4.99 out of 5 average rating, 153 reviews

A vibrant pink pool float with the text 'OUT OF OFFICE' is placed in the clear blue water of a private swimming pool. Additional pool floats in various colors are visible, creating a playful atmosphere. Lush greenery surrounds the pool area.

Home in Lake Worth

Tranquil Vibes ~ Pet Friendly Private Pool Home

Welcome to our cozy pool home with screened porch, deck w/ remote control lighting of cabana for evenings. Grill, tropical fruit trees, plants & private fenced yard. Coastal cottage decor mixing vintage finds in newly remodeled space. Neighborhood is peaceful w/ close drive to beaches, restaurants, golfing, parks & shopping. Each bedroom has cooling mattress pads & ceiling fans. Pets welcome! Beach chairs, cooler, bikes, beach umbrella, pool floats, yoga mat, games/books-.Long stays welcome

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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.

4.97 out of 5 average rating, 106 reviews

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.

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4.94 out of 5 average rating, 265 reviews

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.

Home in Delray Beach

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!

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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.

4.98 out of 5 average rating, 105 reviews

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.

Indoor spacesFamilyLayout

4.9 out of 5 average rating, 155 reviews

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.

Home in Delray Beach

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!

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An open dining area features a wooden table set with white dishware and elegant glassware, surrounded by light-colored upholstered chairs. The kitchen is visible in the background, showcasing modern appliances and cabinetry. A comfortable living area can be seen through a large glass door.

4.98 out of 5 average rating, 178 reviews

Impeccable 3BR Home Near Beaches & Atlantic Ave

Great single family home in lovely neighborhood just north of Delray Beach city limits. Home is located 2.5 miles away from the beautiful public Delray Beaches and the famed Atlantic Ave. The home itself has been completely renovated and fully renovated with new modern finishes and patio in back. Yard is completely fenced for your privacy with fruit trees. For families traveling with children, we do have a pack 'n' play, high chair and travel stroller upon request.

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4.99 out of 5 average rating, 114 reviews

Cottage in Delray Beach

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.

Indoor spacesFamilyLaundry

4.79 out of 5 average rating, 272 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!

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A light-colored kitchen features a granite countertop with two metal bar stools. Glass-front cabinets display an assortment of colorful dishware. An archway leads to the adjoining space, while textured tile flooring enhances the area with a warm touch.

4.95 out of 5 average rating, 175 reviews

Private Heated Pool Getaway Near Downtown Delray

Welcome to your perfect getaway in a beautiful first-floor duplex, nestled in a quiet, family-friendly neighborhood just minutes from vibrant downtown Delray Beach. You’re less than a 10-minute drive to the beach and all the amazing restaurants, shops, and nightlife Delray has to offer. Relax in your private pool and backyard oasis, complete with a BBQ grill – perfect for enjoying sunny Florida days and warm tropical evenings.

Indoor spacesFamilyWalkability

4.92 out of 5 average rating, 133 reviews

The living area features a sectional sofa in a neutral tone, complemented by a wooden coffee table. A wall-mounted television is positioned across from the seating. Natural light floods the space through large windows, which are adorned with sheer white curtains, enhancing the airy atmosphere.

Cottage in Delray Beach

Blue Beach Cottage- 1.2mi from Beach!

Great little cottage style home just steps to the beach and walking distance to Delray's famous Atlantic Avenue. A true old Florida home with all of its charm! Walking to distance to an excellent French bakery and the oldest bar in Delray. Very tidy and well kept. All the latest gadgets in this vintage home including; Nest thermostat, smart TVs, strong wifi, and a Ring security system.

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