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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Superhost

A serene outdoor space features a heated saltwater pool with soft blue lighting, complemented by lounge chairs nearby. Lush greenery surrounds the area, providing privacy, while a spacious patio with seating is visible in the background, all under a softly lit evening sky.

Home in Delray Beach

4.86 out of 5 average rating, 28 reviews

Prime Location • Saltwater Pool Retreat with Priva

Welcome to your Delray Beach oasis! This beautifully updated home offers a private saltwater pool, modern furnishings, and a separate fourth bedroom suite—perfect for families or groups looking to unwind in one of South Florida’s top coastal destinations. 🏖 Quick golf cart ride to Atlantic Ave & the beach 🧂 Saltwater pool with spacious outdoor lounge area 🛏 Private guest suite with its own en-suite bath 🍽 Fully equipped kitchen with indoor-outdoor dining spaces 📲 Smart home features + cura

Top guest favorite

The outdoor area features a heated salt-water pool surrounded by tiled patio space. White lounge chairs are arranged beside the water. Lush foliage and umbrellas create a tropical ambiance, while a fenced yard offers privacy for relaxation and play.

Cottage in Delray Beach

4.99 out of 5 average rating, 96 reviews

Luxury Downtown Tropical Oasis- Pool & fenced yard

Welcome to the Happy Mango Hideaway! This charming cottage is nestled in the heart of the Historic Art District and offers a peaceful retreat from the hustle and bustle of downtown. With heated salt-water pool and private fenced in yard, you can relax and unwind in a tropical paradise. The location of the Happy Mango is unbeatable. You'll be steps away from The Ave's best restaurants, shops and attractions. Whether you're here for a romantic getaway or family vacation, book your stay today.

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, 203 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.

Top guest favorite

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.

Home in Delray Beach

5 out of 5 average rating, 23 reviews

WP Delray Waterfront, Pool, Tiki Hut & Putting Grn

DELRAY NIGHTLY offers 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 features a gourmet kitchen, open living space, king beds, and smart TVs in every bedroom. Just 10 minutes from Atlantic Avenue and sandy beaches, with quick access to Boca Raton’s upscale shopping, dining, golf, and nightlife. Your perfect Florida escape awaits—book your dream getaway now!

Guest favorite

Home in Delray Beach

4.95 out of 5 average rating, 95 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

Home in Delray Beach

4.95 out of 5 average rating, 37 reviews

Paradise Pointe East Delray Pool Home

Welcome to Delray''s most coveted locations on this quiet, family-friendly street just minutes from downtown Atlantic Avenue and beautiful beaches. This charming home mixes traditional and modern chic. The single story Home features hardwood floors throughout. Equipped with 3 bedrooms and 2.5 bathrooms, fully stocked kitchen and two living areas. Tropical backyard oasis featuring heated pool with ample space for entertaining, spending time with family, or just basking in the sun.

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, 137 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 in Delray Beach

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.

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.