Vacation rentals with a pool in Delray Beach

4.99 out of 5 average rating, 107 reviews

A spacious heated pool is surrounded by travertine decking, with lounge chairs and a shaded umbrella positioned for relaxation. Lush tropical plants and trees create a private atmosphere, while a grill is nearby for outdoor cooking.

Home in Flamingo Park

Luxe Casa w/ Gorgeous Pool + Terrace Near Downtown

This historic Flamingo Park home has been completely revamped, boasting contemporary finishes, minimalist decor, a custom Italian kitchen + a large outdoor space, ideal for wining & dining. The heated saltwater pool includes steps where you can relax w/ a cocktail + space for swimming - perfect for the entire family. Only steps from chic restaurants, cafes, the Norton museum & both the Kravis + Convention Centres. On top of that, you're only minutes away from world-class beaches & downtown WPB!

Apartment in Delray Beach

A light-colored sectional couch is positioned in a welcoming living area featuring hardwood floors. A large television mounted on the wall displays a serene beach scene. Two artworks adorn the wall beside the couch, and a stylish lamp provides soft illumination.

5 out of 5 average rating, 12 reviews

Exclusive stay in the heart of sunny Delray Beach

Indulge in coastal living in this exquisite, fully remodeled apartment. Perfect for a relaxing getaway in one of Florida's most desirable cities. Amenities include two pools, hot tub, fitness center, tennis courts and a clubhouse. The community is safe & quiet. Ideally located being 1 mile away from the beach, 5-minute drive from the renowned Atlantic Av, shopping and supermarkets within walking distance. This turnkey condo is perfect for vacations or long term stays. Subject to HOA approval.

The private pool area showcases a sparkling blue pool, complete with a spa and sun loungers beneath vibrant red umbrellas. Lush greenery and tranquil waterfront views create a serene atmosphere, inviting relaxation and enjoyment under a bright blue sky with fluffy white clouds.

4.94 out of 5 average rating, 119 reviews

Waterfront Htd Pool, Spa, Pool Table, Lanai, Canal

Indulge in this luxurious 4BR 2BA haven on a picturesque waterfront property in a prime location in Delray Beach, FL. This spacious getaway offers the perfect retreat from bustling crowds with its trendy design, high-end comforts, and scenic backyard that will leave you in awe. ✔ 4 Comfortable Bedrooms ✔ Open Design Living + Pool Table ✔ Fully Equipped Kitchen ✔ Screened-In Porch ✔ Backyard (Swimming Pool, BBQ, Dining, Dock) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

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, 212 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, 8 reviews

A modern kitchen features sleek white cabinetry and an island with a textured countertop. Stainless steel appliances are displayed alongside a gray backsplash. Bright overhead lighting creates an open atmosphere, while large windows provide natural light and a view of the adjacent living area.

Condo in Delray Beach

Beautifully Remodeled 2 Bedroom + Pool

Leave your worries behind. 1 month minimum Come to the Delray Racquet club in sunny South Florida to unwind and relax in this bright and clean condo. All the amenities await you in this beautiful two bedroom two bath unit. Brand new kitchen with all modern appliances and cookware. Open concept is perfect for entertaining. Master bedroom has brand new king bed and the guest bedroom has 2 twin beds. Peaceful patio with lake view to relax and feel the warm breeze. Minutes from beach and Atl

The outdoor space features a cozy firepit surrounded by several chairs, with a tiki hut providing shaded seating. A grill is positioned nearby. The heated pool overlooks the waterway, while vibrant sunset colors reflect in the sky, creating a tranquil atmosphere.

5 out of 5 average rating, 26 reviews

702A Delray Waterfront, Pool, Tiki Hut + Putting G

DELRAY NIGHTLY presents Waterway Palms House, a luxurious waterfront vacation rental in beautiful Delray Beach! Unwind in the heated pool, play on the putting green, relax by the firepit, or dine under the Tiki hut. Inside, enjoy a gourmet kitchen, open living space, king beds, and smart TVs in every bedroom. Just 10 minutes from Atlantic Avenue and sandy beaches, with easy access to Boca Raton’s upscale shopping, dining, golf, and nightlife. Your perfect Florida escape awaits—book now!

4.95 out of 5 average rating, 103 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!

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.

4.92 out of 5 average rating, 138 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!

Superhost

A private backyard features a newly designed pool surrounded by a spacious patio. Six loungers are positioned nearby, and a seating area is visible adjacent to the pool, offering a relaxing outdoor space. Lush greenery and palm trees enhance the serene environment.

4.67 out of 5 average rating, 33 reviews

Beautiful home in Delray! Minutes from boca

Beautiful house located in Delray. **Please note house is currently for sale. There will be no open houses scheduled during stays. However, should there be a request for a private showing, we will give you reasonable notice of a 15 minute window needed for a quick showing. Should the house go into contract and the house is needed for anything relevant to the sell (inspection, handyman work, etc), a minimum notice of 24 hours will be given. Tha you for your understanding.

A heated pool invites relaxation, surrounded by a serene yard with tropical palm trees. Colorful floats rest on the water's surface, while sun loungers and conversation chairs provide ample seating for enjoying the outdoors.

4.95 out of 5 average rating, 124 reviews

Heated Pool | King Bd | Cozy Backyard | Quiet Stay

Feel right at home at The Royal House, nestled in a peaceful, private neighborhood perfect for a relaxing family retreat. Experience year-round enjoyment with our heated pool, ensuring an endless swimsuit season. Whether it's day or night, warm or cool, the pool is ready for you to dive in and unwind in a private and peaceful setting. Ideal location: 10 minute drive - Downtown Atlantic Ave 10 minute drive - Beach 5 minute drive - Kings Point 5 minute drive - I-95 & Turnpike

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 glimmering pool is framed by a spacious patio, adorned with light-colored tiles. Tall palm trees provide greenery in the background, while a dining set stands invitingly nearby. The modern white house complements the serene outdoor environment.