Holiday rentals with a pool in Highland Beach

Sea-Renity- Paradise Oasis by Ocean w/ Pool & Spa

Remodeled duplex welcomes you to a beautiful private paradise oasis! It's the perfect atmosphere designed for family fun and pure relaxation. Enjoy a heated saltwater pool, hot tub and sun shelf. The tiki hut is perfect for sitting around the fire pit, enjoying a BBQ and sipping cocktails. A recently added outdoor TV can be viewed from the tiki hut or hot tub. Inside, relax to a 75” TV, TVs in all bedrooms, fast Wi-Fi and a fully furnished kitchen. About a mile to the ocean, restaurants & shops.

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.

Steps to Private Beach, Pool, Private Patio 19-3

Come stay at this beautifully furnished villa in the exclusive community of Highland Beach. Located directly across from the beach, minutes to Atlantic Avenue in Delray or Mizner Park in Boca Raton. High end finishes throughout in this single story villa showcasing 2 bedrooms, 2 full baths that sleeps 8! Enjoy the 2 car parking, fenced in patio, community pool and private beach access on A1A. Ease of access with only two steps at entry and a keyless entry smart lock. Pet friendly up to 2 pets!

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.

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.

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!

Luxury villa beach ,private patio

My place is a short walk to a private beach, night life, family-friendly activities, public transport. You’ll love my place for the views, the people, and the location. The place is good for couples, solo adventurers, business travelers, and families (with kids). Included is a high chair and crib pen. There is a private patio with a barbecue, table and chairs for dining outside. Great pool with lounge chairs only available for total of 8 villas to use! Perfect Getaway!

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.

Waterfront Htd Pool, Spa, Billiards, Lanai, Canal

🌴 Relax at this luxury waterfront Delray Beach retreat in Delray Beach, featuring a heated pool & spa, private dock, screened porch with string lights & Smart TV, pool table, BBQ, and canal views. Bright open living and flexible sleeping for up to 10 guests make it perfect for families and groups seeking comfort, space, and true South Florida relaxation. Message us today and enjoy waterfront luxury, sunshine, and relaxation — all in one exceptional stay. 🌴☀️

944 Large Home in Tropic Isles | by Brampton Park

Exclusively Managed by Brampton Park Heated Pool, Pet Friendly 4 Bedroom 3.5 Bathroom Family Home located in Tropic Isles Expansive views of the water from the backyard and master suite, and bedroom 3 (with balcony) High end furnishings and appliances throughout Beautiful formal living room with wet bar and cozy family room with large TV and sound bar Cafe, restaurants just 1/2 a mile away, Fresh market *Use of the Dock requires Prior Approval*

3/2 Private Home in East Delray + pool & gas grill

Welcome to Blue Heron featuring: • Fully renovated 3BR/2BA home • Primary bedroom features King-size bed • Private pool & fenced backyard • Quiet, safe East Delray neighborhood • 1 mile to the beach • Minutes to Atlantic Ave, Mizner Park & FAU • Modern kitchen & stylish décor • Sun loungers + gas grill • Fast Wi-Fi • Smart TVs • Washer/dryer • Ideal for families, couples & remote workers • Managed by experienced Superhosts