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.

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

Beautiful 1 bedroom condo located directly on the intracoastal with a heated pool. This unit DOES NOT have water view from the condo BUT has amazing views of the intracoastal waterway from the patio/pool area. Enjoy watching the yachts sail by along with taking in amazing sunsets from the dock. Work from home, 1 block from the beach! Quiet and peaceful. Within walking distance to many shops and local amenities! Perfect for couples, young families and groups of friends traveling together.

Newly Renovated 1BR apartment in the heart of WPB

This beautifully remodeled one-bedroom, one-bath apartment offers a bright open-concept layout with a full kitchen and spacious living area. Thoughtfully furnished with your comfort in mind, the space feels warm and inviting, with lush greenery and stylish details throughout. The bedroom features a king-size bed and closets for ample storage. The modern bathroom boasts a stunning custom walk-in shower. Just two blocks from the water, this is the perfect blend of comfort, style, and location.

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.

Key West Style Suite with Pool/Spa

This beautiful Key West Style studio with kitchen and WIFI is located in the historic neighborhood of Flamingo Park. It’s close to restaurants, downtown Rosemary Square, the Norton Art Museum, the WPB Convention Center, the Palm Beach International Airport, the instracoastal waterway and 5-10 minUte drive to Worth Avenue in Palm Beach and the Palm Beaches. We welcome couples, solo adventurers and business travelers who can enjoy a private backyard guest suite with salt water pool and spa.

Jungle Oasis with Heated Pool, Tiki Hut & Hot Tub

Welcome to your sunny West Palm Beach getaway. This beautiful home offers a heated pool, perfect for relaxing after a day of exploring the town or nearby beach. Conveniently located, it's just minutes from the PBI airport and downtown West Palm and a short walk to the zoo making it an ideal day out for families. The house has 3 spacious bedrooms, 2 modern bathrooms, and a fully stocked kitchen, providing all the comforts of home in a tropical setting. Enjoy the Florida sunshine in style!

Spacious Designer Home Htd Pool Near Atlantic Ave

🌴 Enjoy this spacious Delray Beach retreat in Delray Beach, featuring a resort-style heated pool with sun shelf, fire pit, BBQ Ggill, cornhole, and a private backyard oasis. Inside, relax with soaring two-story living, fireplace, and modern open spaces. Comfortable bedrooms make it perfect for families and groups seeking fun, relaxation, and easy access to beaches and Atlantic Ave. Message us today and enjoy sunshine, space, and unforgettable memories — all in one perfect 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!

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!

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.

Vintage Vibes by the Beach – Walk to Atlantic Ave!

Discover Delray Beach’s best-kept secret: our vintage-style 1-bedroom, 1-bath hideaway. Tucked just off Atlantic Avenue behind the luxurious Opal Grand hotel, this charming king-bed retreat is perfect for a beach escape. Less than a 2-minute walk to Delray’s sandy dunes, it’s both near the vibrant bars and restaurants and peacefully hidden away. This modern, cozy space offers all the comforts of home in a vacation-style setting.

Renovated Townhome w/ Pool&Gym in Gated Community

Come experience our inviting townhome,located in a peaceful gated community where you'll find the soothing vibes of the beach mixing effortlessly with modern luxury. Right in the heart of lively Delray Beach, our place gives you quick access to both the sunny shoreline and the vibrant downtown scene. Whether you're looking for a serene getaway or an exciting adventure, our townhome is ready to be your ideal retreat.