Vacation rentals with a pool in Gulf Stream

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, 93 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.

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.

5 out of 5 average rating, 52 reviews

A light-filled living area features a comfortable sofa adorned with colorful cushions. Two windows are framed by navy blue curtains, allowing natural light to illuminate the space. A round dining table is positioned near the window, accompanied by two white chairs, creating a cozy spot for meals.

Condo in Delray Beach

Guest Favorite 3 Min Walk to Beach & Atlantic Ave

3 minute walk to both the beach and Atlantic Ave! This is the perfect location!!! 5 stars for comfort, cleanliness, style, and walking distance from everything. FREE Parking: No need to worry about finding a spot or skip the car and walk everywhere! Pool Access: Relax and unwind in the pool. Court Yard Seating: Enjoy your morning coffee or an evening drink in our cozy courtyard with umbrellas for shade. Enjoy the The Opal Hotel Spa just a block away or drop into the new Pura Vida Miami!

Luxe

5 out of 5 average rating, 43 reviews

Heart of Delray ~ Luxury 2bd~ Private Pool & Spa

Experience this beautifully appointed vacation retreat just minutes from Pineapple Grove, Atlantic Avenue, and Delray Beach. Enjoy a tranquil private saltwater pool and spa surrounded by lush tropical landscaping, comfortable lounge seating, and a charming patio. The chef’s kitchen overlooks the pool and is fully equipped for true gourmet cooking. Completely remodeled and professionally furnished, this two-bedroom, two-bath home offers the perfect blend of comfort, style, and relaxation.

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, 118 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!

4.99 out of 5 average rating, 103 reviews

Cottage in Delray Beach

Happy Mango | Heated Pool | Walk to Atlantic Ave

Escape the winter chill and kick back 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.

A modern living area features a light gray sectional sofa, a simple wooden coffee table, and a colorful area rug. Natural light fills the space through large windows, creating a bright and airy atmosphere.

4.92 out of 5 average rating, 49 reviews

Modern renovated oasis home with private pool

Escape to your beach oasis in the heart of Boynton Beach, where modern luxury meets vibrant tropics. Less than 5 minutes from shopping centers, restaurants, Ocean Ridge Beach, and Lake. Features include a large inground pool, spacious rooms, a fully equipped kitchen, onsite laundry and dryer unit, yard games (cornhole), and a gigantic living space! Whether you're seeking adventure or simply craving a peaceful retreat, our home offers the perfect blend of convenience and serenity.

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, 148 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!

4.95 out of 5 average rating, 107 reviews

Canal, Htd Pool, Putt-Putt, Pergola, Air Hockey

🌴 Enjoy this waterfront Boynton Beach escape in Boynton Beach, just one block from Caloosa Park. Features a heated private pool, golf putting green, canal-front dock, pergola, BBQ grill, air hockey, fireplace, and stylish interiors with king & queen beds. Perfect for families and groups seeking relaxation, outdoor living, and easy access to beaches and Atlantic Ave. Message us today and enjoy waterfront living, sunshine, and relaxation — all in one exceptional stay. 🌴🌊

4.87 out of 5 average rating, 233 reviews

Condo

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 kitchen features modern white cabinetry and quartz countertops, offering ample space for meal preparation. A large refrigerator and a TV provide convenience, while a view of the backyard and pool enhances the atmosphere. A small dining area can be seen in the background.

4.96 out of 5 average rating, 68 reviews

Bright, open home w/ Pool, close to Delray & Beach

Luxury meets comfort at Boynton Beach East, close to downtown Delray, & beach. This home includes a spacious living room, fully-equipped kitchen, 2 bathrooms, & 3 cozy bedrooms that sleep 8. Outside, you'll find a private oasis complete with a fully fenced yard, patio, and grill. Take a dip in the pool, and relax with your friends and family. Enjoy nearby grocery stores & dining options, as well as easy access to PBI & FLL airports. Discover your next adventure!

A spacious outdoor area features a swimming pool surrounded by vibrant lounge chairs and a dining table. Comfortable seating with striped cushions is available, while a flat-screen TV mounted on the wall offers entertainment options. Lush greenery enhances the inviting atmosphere.