Holiday 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.

Tranquil Vibes ~ Pet Friendly Private Pool Home

Welcome to our cozy pool home with screened porch, deck w/ remote control lighting of cabana for evenings. Grill, tropical fruit trees, plants & private fenced yard. Coastal cottage decor mixing vintage finds in newly remodeled space. Neighborhood is peaceful w/ close drive to beaches, restaurants, golfing, parks & shopping. Each bedroom has cooling mattress pads & ceiling fans. Pets welcome! Beach chairs, cooler, bikes, beach umbrella, pool floats, yoga mat, games/books-.Long stays welcome

1 br 2bed LakeView Rooftop Pool

Escape to this beautifully appointed 1-bedroom, 1-bath condo in the heart of Boynton Beach, just minutes from vibrant downtown Delray. This bright and modern space features two comfortable beds and stunning lake views from the private balcony. Perfect for couples, small families, or solo travelers looking for a relaxing retreat with upscale amenities. Enjoy resort-style living with access to a heated rooftop pool and hot tub overlooking the water, a fully equipped gym, sauna, and steam room.

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 2 - 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

Delray Beachside Retreat 3 min walk to beach!

3 minute walk to both the beach and Atlantic Ave! This is the perfect location!!! 5 stars for comfort, cleanliness, style, and walking distance from everything. FREE Parking: No need to worry about finding a spot or skip the car and walk everywhere! Pool Access: Relax and unwind in the pool. Court Yard Seating: Enjoy your morning coffee or an evening drink in our cozy courtyard with umbrellas for shade. Enjoy the The Opal Hotel Spa just a block away or drop into the new Pura Vida Miami!

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!

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!

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.

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. 🌴🌊

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.