Vacation rentals with a pool in Delray Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Delray Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

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.

Home in Delray Beach

4.9 out of 5 average rating, 208 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 🏖

Superhost

The backyard features a heated pool surrounded by lush greenery and coconut trees. A colorful hammock is suspended between two trees, inviting relaxation. Several lounge chairs are arranged poolside, situated under a clear blue sky. A wooden fence provides privacy to the area.

Home in Delray Beach

4.83 out of 5 average rating, 145 reviews

LUXURY!i - Heated Pool - Perfect Vacation

Beautiful Key West-style house with a gorgeous heated pool. LUXURY! High-end furniture, real wood beds & extremely comfortable mattress. NO IKEA beds here ;) Two story house, 4 bedrooms, 3 full bathroom Heated pool & screened patio Whole Foods, Starbucks, Chick-fil-A, Trader Joe's, Target and so much more just a step away. Located on a quiet, family oriented "no outlet" St 3 min ride to amazing beach, or relax time in the hammock by the pool? Stay with us for YOUR PERFECT VACATION!

Guest favorite

A private heated pool is surrounded by lush greenery and palm trees, fostering a relaxing atmosphere. The pool's bright blue water reflects sunlight, with pink inflatable floats gently bobbing on the surface. Comfortable lounge chairs are positioned nearby, offering a space for leisure.

Home in Delray Beach

4.92 out of 5 average rating, 183 reviews

Delray Beach-5 Bedr/4.5 bath*Heated Pool

Huge comfortable 5 bedroom, 3 ensuite & 2 half bathroom house in sought after Lake Ida area, Delray Beach, FL. Step into a relaxing, beach feel the moment you walk through the door. Enclosed backyard with large private heated pool. Beachtowels, towels, toiletries and all kitchen amenities included. Delray Public Beach: 2miles World renowned Delray Tennis stadium: 1.2 miles. Buzzing Atlantic Ave with restaurants, art galleries: 1 mile Pool loungers, umbrellas & grilling facilities outside.

Top guest favorite

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.

Home in Delray Beach

4.98 out of 5 average rating, 109 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!

Top guest favorite

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.

Home in Delray Beach

4.93 out of 5 average rating, 201 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.

Guest favorite

Home in Delray Beach

4.95 out of 5 average rating, 94 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!

Guest favorite

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.

Home in Delray Beach

4.96 out of 5 average rating, 135 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!

Guest favorite

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

4.87 out of 5 average rating, 214 reviews

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.

Superhost

An aerial view showcases a modern home painted in soft turquoise, surrounded by lush greenery. A sparkling pool is framed by neatly manicured grass, and two umbrellas provide shade over outdoor seating. The inviting atmosphere is complemented by palm trees and a pop of vibrant colors.

Home in Delray Beach

4.95 out of 5 average rating, 87 reviews

The Dream Delray/ 4 BR En-suite Pool Home

Dreams Delray is a modern 4 bedroom 4 1/2 bathroom (4 Bedroom En Suites) heated pool home which is a 10 minute walk to "The Ave,” Delray Beach's popular downtown venue, and a short 5 minute drive to our famous sandy beaches. It has everything you can ask for the perfect family vacation or a small getaway to sunny Florida. The home offers a top chef kitchen open floor plan, surround sound and a wonderful view of the pool from just about every part of the house.

Top guest favorite

Home in Delray Beach

4.98 out of 5 average rating, 46 reviews

HP Delray Retreat: Pool, Tiki Hut & Putting Green

DELRAY NIGHTLY presents Hideaway Palms, your private 3BR oasis in sunny Delray Beach! This renovated villa features a heated pool, tropical Tiki Hut dining area, and a golfer’s dream putting green. Enjoy modern amenities, spacious outdoor living, and comfort for up to 6 guests. Located in the FreeBee ride zone—just minutes from Delray’s beaches, Atlantic Avenue, dining, and nightlife. A perfect escape for friends or family—book your unforgettable stay today!

Guest favorite

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.

Home in Delray Beach

4.91 out of 5 average rating, 219 reviews

Lux 2 King beds 4 Br2 bath, walk to everything.

Professional Hospitality, sparkly clean, luxurious finishes, organic cotton & down beddings. Teak furniture and a relaxing tub. Relaxing outdoor patio and dining. Only 2 walking blocks from the vibrant Atlantic Ave and shuttle to the beach (no need to drive anywhere!!!). Great for families or a group. No Pets no exception. ABSOLUTELY NO SMOKING- INDOOR and OUTDOORS. **If you are a smoker, kindly, DO NOT consider staying here.

Guest favorite

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.

Home in Delray Beach

4.93 out of 5 average rating, 110 reviews

Heated Pool! 1 Mile To Beach & Atlantic Avenue!

COZY COTTAGE STYLE HOME W/COASTAL FINISHES, BEAUTIFULLY FURNISHED IN THE HEART OF DELRAY BEACH. THIS BEAUTIFUL HOME INCLUDES 3 BEDROOMS & 2 BATHROOMS & A LARGE HEATED POOL! 1 MILE TO THE BEACH, ATLANTIC AVENUE, WATER-SPORT ACTIVITIES, FINE AND CASUAL DINING, NIGHT LIFE & UPSCALE SHOPPING & MINUTES TO BOCA RATON. BEAUTIFUL COVERED PATIO TO GRILL AND RELAX ON SOME LOUNGE CHAIRS WHILE OVERLOOKING THE LARGE HEATED POOL!