Vacation rentals with a pool in Gulf Stream

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.

Large Heated Pool - Family Friendly Private BBQ

Welcome to our renovated family-friendly home centrally located in the heart of Boynton Beach, Florida. This home is perfect for families seeking a spacious and friendly retreat. With 3 bedrooms, 4 beds, 2 full bathrooms, and a fully stocked kitchen and laundry area, we've ensured a relaxing and convenient stay for up to 8 people. Take a dip in our newly built saltwater HEATED pool or relaxing in the hammock's backyard, along with a bbq grill and cornhole set for you and your guests to enjoy.

Tiki Hut, Htd Pool, Bar & Putting Greens Near Ave

🌴 Stay in this elegant downtown Delray Beach retreat in Delray Beach, just blocks from Atlantic Ave dining, shopping, and nightlife. Enjoy a heated private pool, tiki hut with bar & Smart TV, 2 putting greens, cornhole, Connect Four, BBQ grill, and a fully fenced backyard. Bright open living and flexible sleeping make it ideal for families and groups seeking walkable convenience and a private tropical escape. Message us today and enjoy the best of Delray Beach—right outside your door. 🌴☀️

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.

Sundy Apartments Unit 3 - Managed by Brampton Park

Modern 2BR Apartment | 1 Block to Atlantic Ave | Walk to Beach + Pool Exclusively Managed by Brampton Park Enjoy the best of Delray Beach from this stylish, 2-bedroom, 1-bath apartment—just one block from Atlantic Avenue and less than a mile from the beach! • Modern, fully equipped kitchen & living space • Two comfortable bedrooms + updated bathroom • Washer & dryer • Shared heated pool, outdoor seating, BBQ grill • Pet friendly (with approval) Construction noise possible thru April 2026

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.

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!

Downtown Beach Home w/FREE Beach Cabana membership

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!

Red Palm Villas

Step into your very own oasis at this incredible property! Whether you're a dedicated yogi, an urban explorer, or simply someone seeking a sense of community and inner peace, you've found your haven here. With a dedicated Zen Den, lush gardens, and an atmosphere that practically exudes "namaste," this place is the ultimate retreat for those in search of balance and serenity. Embrace the harmonious vibes and make this your urban escape where tranquility meets urban exploration.

30 Luxe 4BR Villa | Heated Pool, Tiki Hut & Fun

DELRAY NIGHTLY presents Paradise Palms — a 4BR/3BA luxury villa in Delray Beach with a heated pool, hot tub, ping pong, cornhole, and screened terrace for dining and lounging. Sleeps 8 with plush king beds, Smart TVs, high-speed Wi-Fi, and beautifully renovated modern interiors. Located in the FreeBee shuttle zone, just minutes from Atlantic Avenue, pristine beaches, top dining, shopping, nightlife, and cultural attractions. Perfect for families, friends, or getaway groups!

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.