Vacation rentals with a pool in Delray Beach

A tropical backyard is showcased, featuring a kidney-shaped pool surrounded by palm trees and lounge chairs. A nearby deck area includes a dining table under a vibrant red umbrella. The bungalow's exterior is visible in the background, completing the serene outdoor setting.

4.9 out of 5 average rating, 203 reviews

Grab Flip Flops & Wine Glasses ✦ RELAX ✦ Welcome!

• 6 blocks to downtown restaurants, boutiques, bars (Atlantic Ave) • 10 blocks to beach 🏝 • 1940's Key West style bungalow & private cottage • Tropical fenced-in backyard, pool & deck • Freebee™ Electric cart rides all over Delray Beach • Cozy, comfy, beachy interior • Secure, keyless entry w/ parking for 3 cars • Coffee + Tea bar • All chef essentials provided, dog-friendly, infant pack-n-play, outdoor BBQ, washer & dryer, beach chairs/towels/umbrella, 2 cruiser bikes, pool floats & more 🏖

4.99 out of 5 average rating, 88 reviews

Cottage in Delray Beach

Luxury Downtown Tropical Oasis- Pool & fenced yard

Welcome to the Happy Mango Hideaway! This charming cottage is nestled in the heart of the Historic Art District and offers a peaceful retreat from the hustle and bustle of downtown. With heated salt-water pool and private fenced in yard, you can relax and unwind in a tropical paradise. The location of the Happy Mango is unbeatable. You'll be steps away from The Ave's best restaurants, shops and attractions. Whether you're here for a romantic getaway or family vacation, book your stay today.

4.87 out of 5 average rating, 212 reviews

Condo in Delray Beach

Retro charm studio steps from beach & Atlantic Ave

Charming studio with vintage vibes and a serene location near Atlantic Avenue, and a 2-minute walk from the beach & Opal Grand Beach Hotel. Step into a bygone era, exuding the nostalgic vibes of the 1950s in one of Delray Beach’s most coveted locales. Enjoy the Grove Condominiums with its old-world charm, pool, and tropical gardens. Experience Delray Beach's retro essence with upscale bars, diners, and boutique stores nearby. Embrace classic charm and coastal living in this slice of the '50s.

Superhost

The backyard features a heated pool surrounded by lush greenery and coconut trees. A colorful hammock is suspended between two trees, inviting relaxation. Several lounge chairs are arranged poolside, situated under a clear blue sky. A wooden fence provides privacy to the area.

4.83 out of 5 average rating, 141 reviews

LUXURY!i - Heated Pool - Perfect Vacation

Beautiful Key West-style house with a gorgeous heated pool. LUXURY! High-end furniture, real wood beds & extremely comfortable mattress. NO IKEA beds here ;) Two story house, 4 bedrooms, 3 full bathroom Heated pool & screened patio Whole Foods, Starbucks, Chick-fil-A, Trader Joe's, Target and so much more just a step away. Located on a quiet, family oriented "no outlet" St 3 min ride to amazing beach, or relax time in the hammock by the pool? Stay with us for YOUR PERFECT VACATION!

4.92 out of 5 average rating, 194 reviews

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.

5 out of 5 average rating, 7 reviews

246 - 1 mile to beach, 1 mile to Atlantic

Managed Exclusively by Brampton Park Heated Saltwater Pool, Pet Friendly 3 Bedroom 2 Bathroom Home With Heated Private Pool Amazing location - under 1 mile to the beach, under 1 mile to Atlantic Ave and just half a mile to Pineapple Grove Arts district, Endless dining and entertainment options within walking distance - the nearest cafe is just a couple hundred yards Modern, upscale furnishings throughout. Recently remodeled bathrooms and kitchen, the home is very bright and airy.

4.97 out of 5 average rating, 88 reviews

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!

Apartment in Delray Beach

The backyard oasis features a heated saltwater pool with a waterfall and surrounding tropical landscaping. A Polynesian-style Chickee hut offers seating and a shaded lounge area. A pink inflatable float adorns the pool, adding a splash of color to the serene setting.

5 out of 5 average rating, 26 reviews

Tiki Hideaway Blocks to Avenue w/ Pool & Spa

Welcome to Casita Delray. Just 4 blocks from Atlantic Ave. One block to Pineapple Grove. Only a 1.25 mile walk to the beach or use the “Freebee” app to call a free golf cart to take you to the beach restaurants shops etc etc. Many Delray favorites and necessities right around the corner such as The French Bakery, Putting Around,PopStroke, Cigar lounges, Coffee houses, restaurants, bars, Publix and Walgreens to name a few. We look forward to hosting your downtown Delray experience.

Beach chairs are set up under large blue umbrellas on white sand. The tranquil ocean waves can be seen in the distance, blending into a clear sky with soft clouds. A sign indicates that a beach membership is included with the stay.

4.92 out of 5 average rating, 130 reviews

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!

4.96 out of 5 average rating, 114 reviews

Heated Pool | King Bd | Cozy Backyard | Quiet Stay

Feel right at home at The Royal House, nestled in a peaceful, private neighborhood perfect for a relaxing family retreat. Experience year-round enjoyment with our heated pool, ensuring an endless swimsuit season. Whether it's day or night, warm or cool, the pool is ready for you to dive in and unwind in a private and peaceful setting. Ideal location: 10 minute drive - Downtown Atlantic Ave 10 minute drive - Beach 5 minute drive - Kings Point 5 minute drive - I-95 & Turnpike

An outdoor area features a cozy firepit surrounded by sleek seating, perfectly situated near the water. A Tiki hut provides shade with ample seating and a grill visible to the side, while the scenic waterway is framed by lush greenery under a colorful twilight sky.

5 out of 5 average rating, 17 reviews

WP Delray Waterfront, Pool, Tiki Hut & Putting Grn

Luxurious waterfront living at its best in Delray Beach! Amazing heated pool, putting green, firepit, privacy, and Tiki hut for lounging & dining. Indoor living features a true gourmet kitchen, spacious living room & dining with incredible views. King beds and large TV's in every bedroom. Located just 10-minutes from Atlantic Avenue and the beach, this property offers easy access to everything Delray and Boca have to offer. Book this unforgettable waterfront retreat now!