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.

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 4 - 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!

Canal, Htd Pool, Putt-Putt, Pergola, Air Hockey

🌴 Enjoy this waterfront Boynton Beach escape in Boynton Beach, just one block from Caloosa Park. Features a heated private pool, golf putting green, canal-front dock, pergola, BBQ grill, air hockey, fireplace, and stylish interiors with king & queen beds. Perfect for families and groups seeking relaxation, outdoor living, and easy access to beaches and Atlantic Ave. Message us today and enjoy waterfront living, sunshine, and relaxation — all in one exceptional stay. 🌴🌊

FP Delray Delight: Saltwater Pool & Serene Oasis!

Delray Nightly presents Flamingo Palms — a stunning 4BR, 2BA luxury villa with heated saltwater pool, private putting green, 75″ Smart TV, and chef’s kitchen. Enjoy high-speed Wi-Fi, dedicated workspace, and Freebee — a complimentary on-demand electric shuttle for easy trips to Delray Beach, Atlantic Avenue dining, shops, beaches, and vibrant nightlife. Perfect for families, couples, or remote work escapes. Flamingo Palms blends resort comfort with home-style relaxation.

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.

Bright, open home w/ Pool, close to Delray & Beach

Luxury meets comfort at Boynton Beach East, close to downtown Delray, & beach. This home includes a spacious living room, fully-equipped kitchen, 2 bathrooms, & 3 cozy bedrooms that sleep 8. Outside, you'll find a private oasis complete with a fully fenced yard, patio, and grill. Take a dip in the pool, and relax with your friends and family. Enjoy nearby grocery stores & dining options, as well as easy access to PBI & FLL airports. Discover your next adventure!

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!