Holiday rentals with a pool in Delray Beach

Delray Holiday Escape • Heated Pool • Walk to Ave

Escape the winter chill and celebrate the holidays in sunny Delray Beach! The Happy Mango Hideaway is a private 2-bedroom, pet-friendly cottage featuring a heated saltwater pool, spa-style bathroom (renovated Oct 2025), full kitchen, fast Wi-Fi, and cozy workspace. Walk to Atlantic Ave’s shops, cafés, and nightlife, or unwind in your fenced tropical yard. Perfect for holiday travelers, snowbirds, and remote workers seeking sunshine and serenity. Make Delray Beach your home for the holidays.

Spacious Designer Home Htd Pool Near Atlantic Ave

Step into the luxe and spacious 4BR 2.5BA oasis in the heart of Delray Beach, FL. It promises a relaxing retreat just a few minutes from bustling Atlantic Ave, sunny beaches, restaurants, shops, exciting attractions, and landmarks. The unique designer ambiance and rich amenity list will leave you in awe. ✔ 4 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Backyard (Heated Pool, Fire Pit, BBQ, Lounges) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry ✔ 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.

702A Waterfront Villa – Pool, Tiki Hut & Putting

DELRAY NIGHTLY presents Waterway Palms — Incredible Luxe rated 3BR/3BA waterfront Delray Beach villa with heated pool, Tiki Hut, firepit, putting green, and outdoor games. Sleeps 8 (incl murphy) with king beds, amazing chef’s kitchen, Smart TVs, high-speed Wi-Fi, and welcome basket with starter supplies. Relax in the large spacious open living areas and enjoy resort-style outdoor fun, just 10 minutes from Atlantic Avenue, beaches, dining, nightlife, golf, and upscale shopping. See you soon!

210 Walk to Pineapple Grove | by Brampton Park

Exclusively Managed By Brampton Park Heated Pool and Pet Friendly 4 Bedroom 3 Bathroom Delightful home, less than 1 mile to the Beach  Modern, upscale downtown Delray home, fully renovated with all new furnishings as of July 2024. While this home is on a quiet residential street, the location is truly unbeatable - 1/4 mile to Pineapple Grove district that is bustling with restaurants, bars and cafes, and The Ray Hotel. Half a mile to Atlantic Avenue, and less than 1 mile to the beach.

Heart of Delray ~ Luxury 2bd~ Private Pool & Spa

Experience this beautifully appointed vacation retreat just minutes from Pineapple Grove, Atlantic Avenue, and Delray Beach. Enjoy a tranquil private saltwater pool and spa surrounded by lush tropical landscaping, comfortable lounge seating, and a charming patio. The chef’s kitchen overlooks the pool and is fully equipped for true gourmet cooking. Completely remodeled and professionally furnished, this two-bedroom, two-bath home offers the perfect blend of comfort, style, and relaxation.

Great Location. Atlantic Ave. Awesome backyard!

Your memorable stay starts with a great central location and easy access to everything! Situated just a 2min drive from the internationally renowned Atlantic Ave, Pineapple Grove, upscale shopping, fine dining, art galleries, and a quick 5min drive to pristine beaches. The newly renovated, 100k backyard is second to none and is sure to provide an exceptional private oasis experience, complete with pool, jet pool , stunning waterfall, sun loungers, fire pit, pergola, bbq and much more

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!

LUXE Lake Oasis I Dock, Pool & Designer Interiors

Indulge in the ultimate Lake Ida luxury retreat at this Boynton Beach waterfront home. With 4 bedrooms, including 2 king suites, 3 bathrooms, a private dock, and a brand-new heated pool with travertine patio and safety fence, this property blends elegance and comfort. Set on nearly half an acre, it boasts professional designer interiors, stunning lake views, and seamless indoor/outdoor living. Sleeps 8, just minutes to Delray Beach, Atlantic Avenue, beaches, dining, and shopping.

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!

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.

Heated Pool, Hot Tub, Pickleball & Putting Green

Discover your own piece of paradise just minutes from Delray Beach’s vibrant Atlantic Avenue and pristine shoreline. This modern 4-bedroom home is ideal for large families, groups, or corporate retreats. Lounge by the private heated pool, unwind in the hot tub, challenge friends on the pickleball court or putting green, catch your favorite shows on a TV in every bedroom, or gather for a memorable feast in the state-of-the-art kitchen.