Vacation rentals with a pool in Gulf Stream

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, 138 reviews

Private & Pet Friendly, Key West-King Bed Cottage

Spend your beach getaway at our cozy and colorful cottage. It’s one of the historic cottages of Lake Worth Beach listed in a bestselling book 'The Cottages of Lake Worth'. Sit back, soak up the sun, and enjoy the splash pool in the private yard, a palm tree paradise. Relax completely in the specious king-bed bedroom. In a walking distance from the cottage are the Lake Worth public beach and Downtown with a variety of restaurants and entertainment venues. Community Golf Club is around the corner.

Superhost

An above ground pool is filled with clear blue water, reflecting the sunlight. A pool ladder leads into the water, and a floatation device is placed in the center. The backyard features a wooden fence and the outlines of nearby structures, creating a private ambiance.

Home in Boynton Beach

4.81 out of 5 average rating, 186 reviews

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

The landscaped backyard features a heated pool surrounded by smooth stones and tropical plants. A hammock hangs between two palm trees, while a turquoise chair and patio seating offer spaces for relaxation. The setting is complemented by the warm glow of a sunset.

4.94 out of 5 average rating, 84 reviews

7min from Beach - Heated Pool, Hot Tub, EV Charger

This is the PERFECT Airbnb for a groups like big families or multiple couples. This listing is NOT shared and FULLY PRIVATE. This is a house that's divided into three private suites. Each have their own bedroom and bathroom. You are requesting to book all three! There is a beautifully landscaped backyard, HEATED pool, HUGE hot tub, & EV car charger. We are a short drive (~6min) to either the beach or Atlantic Ave - the place to be for bars and restaurants. Pack your bags and come relax!

A serene outdoor space features a pool surrounded by tropical landscaping and palm trees. A spacious patio includes seating areas, complemented by a pathway of laid bricks. Sunlight reflects from the clear water of the pool, creating a relaxed atmosphere.

4.93 out of 5 average rating, 214 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.

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!

Superhost

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.

4.94 out of 5 average rating, 144 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!

4.92 out of 5 average rating, 38 reviews

A tranquil water feature adorns the exterior wall, featuring a serene face sculpture. The crystal-clear pool reflects the vibrant greenery outside. Large windows invite natural light, offering a view of the surrounding lush landscape.

Villa in Delray Beach

Red Palm Villas: The Saw Palmetto

Step into your very own oasis at this incredible property! Whether you're a dedicated yogi, an urban explorer, or simply someone seeking a sense of community and inner peace, you've found your haven here. With a dedicated Zen Den, lush gardens, and an atmosphere that practically exudes "namaste," this place is the ultimate retreat for those in search of balance and serenity. Embrace the harmonious vibes and make this your urban escape where tranquility meets urban exploration.

4.98 out of 5 average rating, 50 reviews

312 Delray Retreat: Pool, Tiki Hut & Putting Green

DELRAY NIGHTLY presents Hideaway Palms — a fully renovated 3BR/3BA luxury vacation rental in Delray Beach. Relax in your private heated pool, dine under the authentic Tiki Hut, or practice on the putting green. Perfect for families, couples, or remote workers, this villa sleeps 6 and offers modern amenities, spacious outdoor living, and fast Wi-Fi. Located in the FreeBee shuttle zone, just minutes from Atlantic Avenue, beaches, dining, shopping & nightlife. Book today!

4.87 out of 5 average rating, 219 reviews

A community pool is surrounded by lounge chairs and palm trees, creating a relaxing atmosphere. The clear blue water is inviting, with light reflections visible on the surface. The patio area is spacious, offering a tranquil space for guests to unwind.

Condo in Delray Beach

Retro charm studio steps from 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.

4.95 out of 5 average rating, 62 reviews

A tranquil backyard features a sparkling saltwater pool surrounded by lush greenery and colorful landscaping. Two lounge chairs are positioned beside the pool, providing a place to relax. A white fence offers privacy while the clear blue sky enhances the serene outdoor space.

Home in Boynton Beach

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!

5 out of 5 average rating, 48 reviews

An aerial view showcases the modern home surrounded by lush greenery, with a private heated pool situated in the backyard. Outdoor lounge chairs and a table with an umbrella are visible alongside a well-maintained lawn, creating an inviting outdoor space.

Home in Boynton Beach

Oceans Paradise~ Private beach~ Heated pool ~Bikes

Calling all beach lovers! 1600 feet to private deeded beach! 6 minutes from famed Atlantic Avenue! This stunning, 3-bedroom, 2-bath, heated pool home is perfectly situated steps from pristine sands, the calming sounds of crashing waves & gentle sea breezes. Enjoy an idyllic beach lifestyle, combined with modern comforts & luxury, at your private beachside oasis. Escape to South Florida this winter, Oceans Paradise is your perfect, monthly, Airbnb.

A spacious pool area is surrounded by lush palm trees and vibrant greenery. The water is clear and inviting, reflecting the blue sky above. A spa section is integrated into the pool's design, providing a serene ambiance for relaxation.