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, 137 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.

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.

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

A spacious backyard features a newly built saltwater pool accompanied by lounge chairs. A shaded umbrella offers relief from the sun. A hammock is positioned nearby for relaxation. The well-maintained lawn surrounds the area, enhancing the inviting outdoor space.

4.96 out of 5 average rating, 74 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 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, 105 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 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!

4.98 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.

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.

4.95 out of 5 average rating, 62 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 serene backyard scene features a clear blue pool, surrounded by palm trees and elegant lounge chairs. A shaded gazebo offers a space for relaxation. The pool area overlooks the tranquil waterway, enhancing the natural beauty of this private outdoor retreat.

5 out of 5 average rating, 4 reviews

*NEW*10min to Atlantic Ave Delray | Walk 2 Beach |

Welcome to your serene escape tucked away along Florida’s stunning Intracoastal Waterway. This elegant 2,177 sq ft home offers the best of laid-back luxury and natural wonder — perfect for families, couples, or small groups seeking tranquility, style, and a touch of adventure.10 minute drive to Atlantic Avenue in Delray and walking distance to the beach. #YOLO 🛏️ 3 Bedrooms | 🛁 3 Bathrooms | 🚣‍♂️ Stand up Paddle board included + Jet Ski Ramp

Guesthouse in Boynton Beach

A private swimming pool is framed by a white concrete deck, featuring built-in stairs for easy access. Surrounding tropical landscaping includes vibrant green plants and palm trees. Nearby lounge chairs invite relaxation while a light cloud cover adds to the serene atmosphere.

4.88 out of 5 average rating, 165 reviews

COCONUT CASITA {Delray Beach | Boynton Border}

COCONUT CASITA: Detached studio cottage in east Boynton Beach (Boynton Beach / Delray Beach border) with Old Florida charm. 2 miles to nearest beaches and downtown Delray. 3 miles from Ocean Ave waterfront dining in Boynton Beach. Good for couples, solo adventurers, and small families... Details: Furnished, Cable/Internet included, Queen size canopy bed, Twin/single sofa bed, Full kitchenette, Parking, Private entrance.

A spacious backyard is showcased, featuring a large heated pool surrounded by lounge chairs and tropical landscaping. Outdoor seating is provided under a covered patio, with a barbecue grill visible in the background. Bright blue skies and lush greenery enhance the inviting atmosphere.