House holiday rentals in Delray Beach

A tropical backyard is showcased, featuring a kidney-shaped pool surrounded by palm trees and lounge chairs. A nearby deck area includes a dining table under a vibrant red umbrella. The bungalow's exterior is visible in the background, completing the serene outdoor setting.

4.91 out of 5 average rating, 211 reviews

Grab Flip Flops & Wine Glasses ✦ RELAX ✦ Welcome!

• 6 blocks to downtown restaurants, boutiques, bars (Atlantic Ave) • 10 blocks to beach 🏝 • 1940's Key West style bungalow & private cottage • Tropical fenced-in backyard, pool & deck • Freebee™ Electric cart rides all over Delray Beach • Cozy, comfy, beachy interior • Secure, keyless entry w/ parking for 3 cars • Coffee + Tea bar • All chef essentials provided, dog-friendly, infant pack-n-play, outdoor BBQ, washer & dryer, beach chairs/towels/umbrella, 2 cruiser bikes, pool floats & more 🏖

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, 124 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 bright living area is furnished with a light-colored sofa and two wicker chairs, each with decorative cushions. A rectangular coffee table is centered on a soft area rug. Natural light fills the space through large windows, and a wall-mounted TV is positioned across from the seating arrangement.

4.95 out of 5 average rating, 235 reviews

Peaceful & Roomy Waterfront Delray Beach House

🏝LOCATION, LOCATION, LOCATION! Delray Beach's BEAUTIFUL waterfront property! The Bamboo Beach House is located directly on Intracoastal waterway in Delray Beach. Each unit has private patio overlooking 40 feet of waterfront! Enjoy morning coffee and experience beautiful sunrises with the ocean breeze. Our piece of waterfront is a favorite area of local manatees to swim in with the tides, along with schools of jumping fish! The amazing water views and aquatic wildlife is second to none!

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, 217 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.

A charming casita is set against a lush green lawn, framed by vibrant foliage. The entrance features light blue accents and a small seating area with two white chairs, inviting relaxation. Sunlight casts gentle shadows, enhancing the welcoming appearance of the home's exterior.

4.93 out of 5 average rating, 136 reviews

CASITA DELRAY (314 SW 2nd Street)

Charming Renovated 2 Bedroom “Casita” Close to Downtown Delray Beach!! Beautifully Decorated with thoughtful details throughout Quality Mattresses, Bedding, Plush Pillows,, & Towels, 2 Beach Cruiser Bicycles for a quick ride downtown or to the beach 3 Beach Chairs / Beach Umbrella / Beach Towels / Yoga Mat Provided Private Fenced Backyard with Weber BBQ / Table and Chairs for Outdoor Dining / Hammock. Close to Downtown....Restaurants, Bars, Shoppes, Nightlife and award-winning BEACHES ;)

A private saltwater pool is surrounded by a spacious patio area with multiple seating options. An umbrella provides shade over a large dining table, while string lights add a subtle ambiance. Lush greenery frames the backyard, enhancing the serene outdoor setting.

4.95 out of 5 average rating, 20 reviews

5 Min to Beach ~ Heated Pool ~ Bikes Included

Nestled in historic Delray, this elegant and completely updated home offers 3BD, 3.5BA + office spanning over 2,100 sp ft. The kitchen features quartz countertops + all new appliances. Laundry downstairs and upstairs. Patio w. private salt water pool and seating area with screens. Double garage with 4 bicycles + hanger for your use. Located just a few steps from vibrant Downtown Delray with lots of bars, restaurants, live music, festivals, farmer’s market and just minutes from the beach.

A private dock extends over tranquil waters, framed by lush palm trees. Two blue chairs are positioned on a wooden deck, offering a serene space to enjoy the surrounding nature and canal views. The sky is clear with soft clouds reflecting on the water's surface.

4.98 out of 5 average rating, 189 reviews

shipwrecked fun design • stunning canal view

Bold interior design in this newly renovated pad with a beautiful canal and dock in delray. Step in the front door and immediately you see the large windows looking out onto the water in the back. This is true to Delray Beach with all its charm. Now pop on a movie on the big 75 inch Smart TV screen, rest your head on the comfy beds, shower under the rainfall fixtures and truly unwind in a Delray-geous getaway. Just 6 minutes to the beach or Delray's amazing nightlife and restaurants.

Superhost

A spacious living area is defined by a high, wooden ceiling and neutral tones. A white sofa is positioned against a textured brick wall, accompanied by a round dining table and blue chairs. A large window allows natural light, complemented by a vibrant piece of artwork and decorative elements.

4.86 out of 5 average rating, 138 reviews

2 BD Delray Beach Cottage walk to The Ave & beach

Your friends and family will be close to everything when you stay at this centrally-located trendy apartment in the Historic District of Delray Beach. This newly remodeled mid-century modern apt features a brand new kitchen where guests can gather and cook up their favorite meals. Spend your days tanning and swimming at the beach before relaxing in your private patio for an afternoon drink then walk over to Pineapple Grove and "the Ave" for live music, great food, dancing, and fun!

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, 145 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, 52 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!