Vacation rentals in Highland Beach

Delray Sunshine Cottage with Pool and Beach Pass

Charming Delray Beach cottage with a private saltwater pool and outdoor dining/seating spaces. Like having a two-bedroom hotel suite with your own private pool! Light-filled, relaxing and well-equipped with you in mind. Walk a mile to Atlantic Avenues shops, restaurants & bars. Close to the beach with a pass for lounge chairs and umbrella on any beach! Perfect for couples, solo adventurers or a family of four. Relaxing oasis for a wonderful experience. Unbeatable location for your sunny escape!

Cozy, Comfy, Private Yard

Enjoy beautiful Delray Beach* at a great price. This bright, immaculately clean, cozy apartment has what you need. 10 min. from Atlantic Ave shops/restaurants, 15 min. from the beach. Relax in your spacious well-lit, private yard, stylishly designed with palm trees and plants. Perfect for “chilling out” and for having family/friends join you. DELRAY BEACH: (USA TODAY 2024) #1 BEST BEACH IN FL ONE OF USA'S 10 GREAT SHOPPING STREETS (Atlantic Ave) ID is required for guests without +reviews

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!

Exclusive stay in the heart of sunny Delray Beach

Indulge in coastal living in this exquisite, fully remodeled apartment. Perfect for a relaxing getaway in one of Florida's most desirable cities. Amenities include two pools, hot tub, fitness center, tennis courts and a clubhouse. The community is safe & quiet. Ideally located being 1 mile away from the beach, 5-minute drive from the renowned Atlantic Av, shopping and supermarkets within walking distance. This turnkey condo is perfect for vacations or long term stays. Subject to HOA approval.

Waterfront Htd Pool, Spa, Billiards, Lanai, Canal

Indulge in this luxurious 4BR 2BA haven on a picturesque waterfront property in a prime location in Delray Beach, FL. This spacious getaway offers the perfect retreat from bustling crowds with its trendy design, high-end comforts, and scenic backyard that will leave you in awe. ✔ 4 Comfortable Bedrooms ✔ Open Design Living + Pool Table ✔ Fully Equipped Kitchen ✔ Screened-In Porch ✔ Backyard (Swimming Pool, BBQ, Dining, Dock) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

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.

702A Waterfront Villa – Pool, Tiki Hut & Putting

DELRAY NIGHTLY presents Waterway Palms — Incredible Luxe rated 3BR/3BA waterfront Delray Beach villa with heated pool, Tiki Hut, firepit, putting green, and outdoor games. Sleeps 8 (incl murphy) with king beds, amazing chef’s kitchen, Smart TVs, high-speed Wi-Fi, and welcome basket with starter supplies. Relax in the large spacious open living areas and enjoy resort-style outdoor fun, just 10 minutes from Atlantic Avenue, beaches, dining, nightlife, golf, and upscale shopping. See you soon!

Cozy Delray Beach House Waterfront Intracoastal

🏝LOCATION, LOCATION, LOCATION! Delray Beach's BEAUTIFUL waterfront property! The Bamboo Beach House is located directly on Intracoastal waterway in Delray Beach. Each unit has private patio overlooking 40 ft of waterfront! Enjoy morning coffee and experience beautiful sunrises with the ocean breeze. Our piece of waterfront is a favorite area of local manatees to swim in with the tides, along with schools of jumping fish! The amazing water views and aquatic wildlife is second to none!

Beach Retreat W/Cabana Service | Steps to Downtown

Welcome to your retreat filled with sun & fun, where you can relax in the tropic air and aqua blue waters of Delray Beach. You will enjoy our well-appointed, newly renovated guest house originally built in 1929 & located in historic downtown Delray. Live like locals as you enjoy a bike ride or an evening stroll to our lively downtown and beautiful beaches. With our amenities and superb level of cleanliness, you will experience a level of comfort unmatched by hotels or other Airbnbs

910 Heated Pool & Yard Fun | by Brampton Park

Managed by Brampton Park Rentals Heated Pool, Pet Friendly 3 Bedrooms 2 Bathrooms with covered Lanai Area and Heated Pool. The garden is large & private with access to the intracoastal waterway Perfectly situated with easy and quick access to downtown Delray Beach and Boca Raton. Both Atlantic Avenue and Mizner Park are just a few minutes drive away *Dock use is subject to pre-approval*

Private Luxury Suite

Luxurious private suite with separate entrance attached to a single family home in a central residential quiet Boca Raton neighborhood. Close to beach, Mizner Park, shopping, restaurants & transportation. Unit has separate closet/breakfast bar and well appointed deluxe bathroom. All guests must have a profile photo of themself in order to book this listing.