
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.

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 🏖

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!

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.

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!

October Escape Sale – Don’t Miss Out!
Welcome to Casita Delray. Just 4 blocks from Atlantic Ave. One block to Pineapple Grove. Only a 1.25 mile walk to the beach or use the “Freebee” app to call a free golf cart to take you to the beach restaurants shops etc etc. Many Delray favorites and necessities right around the corner such as The French Bakery, Putting Around,PopStroke, Cigar lounges, Coffee houses, restaurants, bars, Publix and Walgreens to name a few. We look forward to hosting your downtown Delray experience.

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!

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!

Retro charm studio - Walk to 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.

Luxury Delray Beach Heated Pool & Spa Retreat
Relax & play in our 3-bed waterfront home featuring a heated pool, bubbling spa and private putting green—just minutes from vibrant Atlantic Ave. What you’ll love: Lush backyard with pool, spa & BBQ Steps to dock for sunrise coffee Fast Wi-Fi, smart TVs, full kitchen Hotel-quality beds & 5-star cleanliness Solar installed with a Tesla Power wall backup battery for storm resilience. Book now and treat yourself to Delray Beach’s best blend of fun and serenity.

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.

New! Luxury Tropical Oasis - Delray Beach
Escape to this stylish 3-bedroom, 2-bath retreat just minutes from the beach and iconic Atlantic Avenue. With designer interiors, a fully stocked kitchen, luxury outdoor seating, and thoughtful family-friendly touches, this Delray Beach gem is the perfect blend of comfort and convenience. Enjoy complimentary concierge service, plush amenities, and everything you need for an effortless and unforgettable stay in South Florida.

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!
Popular amenities for Delray Beach rentals with a pool
House rentals with a pool

Luxury Delray Beach 4/3 Pool/Spa 2 King Masters

Relaxing Retreat | Pool + Near Beach & Atlantic Av

Marigold Cottage

Luxury Furnishings! Private Heated Pool!

Dream Home steps to the Ocean with a Heated Pool!

•Floasis• Your private FL oasis 5 min to beach!

FP Delray Delight: Saltwater Pool & Serene Oasis!

Bio-Hack Retreat~Heated Pool~Sauna~Plunge~Games
Condo rentals with a pool

1/1 Apartment in Deerfield Beach

Palm Beach Hotel Condominium

Tropical Coastal Resort in Boynton Beach

Luxe King Suite -valet parking-near beach

Ritz-Carlton Beach Penthouse by Guaranteed Rental

ON CANAL! Pool+Walk to BEACH! Boat Watch! 1b/1b

Luxury 2x2 condo, water views & hotel amenities

Modern 3BR Condo • Rooftop Pool • Near Bal Harbor
Home rentals with a private pool

Elegant Getaway Near the Ocean in West Palm Beach

Boca Beauty - Stylish Home with Pool

Tropical Cabana with Pool and Bedroom

Gorgeous Lake Worth Beach House
Quick stats about vacation rentals with a pool in Delray Beach
Total rentals
490 properties
Nightly prices starting at
€ 26 before taxes and fees
Total number of reviews
13K reviews
Family-friendly rentals
370 properties are a good fit for families
Pet-friendly rentals
210 properties allow pets
Rentals with dedicated workspaces
290 properties have a dedicated workspace
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