Vacation rentals with a pool 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, 89 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.

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!

An aerial view captures the tranquil intracoastal waters with boats passing by. Lush greenery and palm trees frame the property, while several waterfront homes are visible in the background. The scene reflects a serene atmosphere characteristic of the East Delray Beach neighborhood.

4.95 out of 5 average rating, 22 reviews

Delray Beach Waterfront 4 Bedroom with Heated Pool

DIRECT INTRACOASTAL WATERFRONT! Watch the passing boat from the private backyard located in a quiet East Delray Beach neighborhood, across from the multi-million-dollar homes of Gulf Stream, Florida. Located within 3 miles from world famous Atlantic Ave in Downtown Delray Beach. Enjoy the top-rated restaurants, shops, nightclubs and the white sandy beach. Centrally located just north of Boca Raton and a short drive to either the West Palm Beach (PBi) or Fort Lauderdale (FLL) airports.

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, 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!

A serene heated pool is surrounded by lounge chairs and umbrellas, set against a backdrop of lush palm trees. The scene is illuminated by the warm colors of a sunset sky, creating a tranquil outdoor living space.

4.98 out of 5 average rating, 51 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!

4.95 out of 5 average rating, 62 reviews

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.

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!

4.93 out of 5 average rating, 162 reviews

A comfortable living area is featured, with a light-colored sofa adorned with decorative pillows and beach-themed artwork on the walls. A wooden coffee table with a coastal design sits in front, complemented by a patterned area rug, creating a relaxed atmosphere.

Condo in Boynton Beach

Tropical Coastal Resort in Boynton Beach

Luxury upscale 1 bedroom condo located at Casa Costa intercoastal in Boynton Beach, FL invites you to explore the intercoastal waterways, beautiful walking and biking trails in the Mangrove Park and Ocean Ridge Park. The condo offers a queen size bed, a well equipped Kitchen, Smart TV, free Wi-fi, and stackable washer and dryer. The resort offers two beautiful pools, Sauna, Steam room, Fitness Center, Business Center and one FREE designated parking spots.

An aerial view showcases the beach cottage nestled in a lush, green landscape, surrounded by various residential properties. The expansive yard is highlighted, featuring a heated pool that glimmers under the sunlight, contributing to the property’s private and spacious atmosphere.

5 out of 5 average rating, 46 reviews

Dream Home steps to the Ocean with a Heated Pool!

Welcome to Blue Haven By the Sea, a charming beach cottage tucked away at the end of a quiet cul-de-sac just off A1A in Delray Beach, FL. This private retreat features 3 bedrooms, 3 full baths, and comfortably hosts 6–8 guests. Enjoy the expansive heated pool, large private yard, and full home access. Perfect for relaxing or entertaining, all just moments from the beach, dining, and vibrant local attractions. Your peaceful coastal escape awaits!

5 out of 5 average rating, 5 reviews

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.

Home in Boynton Beach

*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

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.

Guesthouse in Boynton Beach

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.

An outdoor covered patio features seating arrangements with comfortable furniture, complemented by decorative cushions. A fan hangs from the wooden ceiling, providing a cooling breeze. The lush backyard offers views of a large heated pool surrounded by tropical landscaping.