Holiday rentals with a pool in Delray Beach

SWiSS LiViNG - Lakeside Haven | Pool & Gym

Welcome to SWiSS LiViNG! Enjoy our beautifully designed townhouse in a gated community, just 15 minutes from the beach. Perfect for longer stays and families: - Heated pool - 24h gym, tennis, pickleball & BBQ area - High-speed Wi-Fi & smart TV - Private garden patio - King suite with ensuite & walk-in closet - Queen room with private bath - Fully equipped kitchen - W/D - Parking & keyless entry - Beach & sports equipment Ideal for guests seeking comfort, style and convenience near the coast.

Family · Location · Hospitality

Walker's Tropical Oasis

Enjoy your lush private oasis in Delray's lovely Palm Trail neighborhood! This delightful two-bedroom, one bath mid-century gem with heated pool is four blocks to Atlantic Ave and walking distance to the beach. The property sleeps up to 4 guests comfortably with luxury bed linens and bath towels provided and Smart TVs in each bedroom where guests can sign in with their favorite streaming services. New fully equipped chef's kitchen and screened lanai overlook a hidden tropical courtyard.

Location · Value · Hospitality

Ritzy Coastal Scape

Indulge in coastal luxury at Ritzy Coastal Scape, a masterfully renovated 3BR/2.5BA villa in East Delray Beach. This sleek sanctuary features an epicurean gourmet kitchen and a private backyard oasis with an LED-lit Jacuzzi designed for upscale relaxing. Nestled just two blocks from artisan markets and fine dining, you are a mere mile from the pristine beach and minutes from vibrant downtown Delray. Experience sophisticated tropical living at its finest. Book your elite getaway today.

Value · Location · Layout

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!

Location · Family · Checkout

Private Pool Oasis | Steps to Atlantic Ave

Escape to your own private tropical retreat in the heart of Delray Beach. The Happy Mango Hideaway is a fully private, pet-friendly 2-bedroom cottage featuring a heated saltwater pool, a spa-inspired bathroom (renovated in 2025), a full kitchen, fast Wi-Fi, and a workspace. Spend your days exploring Atlantic Avenue's restaurants, boutiques, galleries, and beaches, all just minutes away. Then return home to relax by the pool and enjoy your private backyard oasis.

Family · Location · Laundry

Luxury Salt Life Meets Bobby Flay

At Dolce Vita Salata, luxury seamlessly intertwines with excitement and comfort to create an unforgettable experience. Every detail, from the plush furnishings to the breathtaking views, is designed to offer the ultimate in relaxation while indulging your senses. Whether you're unwinding in the serene ambiance of the beautifully appointed spaces or exploring the vibrant surroundings, Dolce Vita Salata effortlessly combines elegance with adventure.

Family · Location · Hot tub

Heated Pool, Hot Tub, Pickleball & Putting Green

Discover your own piece of paradise just minutes from Delray Beach’s vibrant Atlantic Avenue and pristine shoreline. This modern 4-bedroom home is ideal for large families, groups, or corporate retreats. Lounge by the private heated pool, unwind in the hot tub, challenge friends on the pickleball court or putting green, catch your favorite shows on a TV in every bedroom, or gather for a memorable feast in the state-of-the-art kitchen.

Location · Family · Amenities

Waterfront, Spa, Htd Pool, Billiards, Lanai, Canal

Bachelorette weekends, birthday trips, family vacations — this is the house groups keep coming back to. Heated pool and spa on a private canal, screened lanai with string lights, billiards, and a dock where guests watch the sun go down. Sleeps 10. Hosts respond in minutes and know every great restaurant and hidden gem in Delray. 5 minutes to Atlantic Ave. Kayaks, paddleboards, and fishing gear included. 5 minutes to the beach.

Location · Family · Checkout

Honey Hole & Bear Den| Heated Pool | Delray Beach

Welcome to the Honey Hole! This family-friendly beach getaway is sure to have any guest relaxing all year round. Situated in a quiet and private neighborhood this home is perfect for all your vacation needs. This completely renovated home is a 5 minute drive down Atlantic Avenue to downtown and the beaches. You can find restaurants, shops, parks, boat tours, and much more locally. We look forward to hosting you!

Family · Location · Hospitality

Heated Pool/Spa & Walk to Beach and Atlantic Ave

Charming home with excellent location one mile away from the beach and one mile away from beautiful Atlantic Ave. Clubs, pubs, restaurants, the beach, and everything Delray Beach has to offer is close enough to walk, yet far enough to be quiet. Two bedrooms, one bathroom, and a wonderful outdoor shower. The pool area is very comfortable and spacious. Come on in and enjoy the South Florida lifestyle.

Location · Value · Indoor spaces

The Vacation Getaway with a Heated Salt Water Pool

Are you looking to escape the cold, work, or just be close to the beach? If so, this stunning vacation home is for you. It includes a saltwater pool with heater, and is minutes away from the beach, restaurants and all that Atlantic Avenue has to offer. You can rest easy knowing that the owners are dedicated to giving you your best vacation experience.

Family · Location · Outdoor spaces

Gorgeous Modern Beach Heated Pool House Sleeps 8

Gorgeous 4BR, 3BA home in Delray Beach with over 3,000 sq ft! Soaring ceilings, modern upgrades, beautifully furnished, elegant and private. Includes a 2-car garage, amazing heated pool, spa, fully fenced yard, outdoor dining, deck, and patio. Fully stocked kitchen and beach essentials—your perfect getaway!

Family · Value · Quiet