Holiday 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.

4.91 out of 5 average rating, 211 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 🏖

A refreshing heated pool features two loungers set in shallow water, providing a relaxing space for sunbathing. A circular table sits between the loungers, flanked by a vibrant patio umbrella. Surrounding greenery offers privacy, creating a serene atmosphere.

4.93 out of 5 average rating, 102 reviews

Spacious Designer Home Htd Pool Near Atlantic Ave

Step into the luxe and spacious 4BR 2.5BA oasis in the heart of Delray Beach, FL. It promises a relaxing retreat just a few minutes from bustling Atlantic Ave, sunny beaches, restaurants, shops, exciting attractions, and landmarks. The unique designer ambiance and rich amenity list will leave you in awe. ✔ 4 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Backyard (Heated Pool, Fire Pit, BBQ, Lounges) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry ✔ Parking Learn more below!

A charming bungalow is surrounded by lush greenery, featuring a brick pathway leading to the entrance. Potted plants with colorful flowers are placed beside the door. The metal roof reflects sunlight, while the blue sky and clouds provide a serene backdrop.

4.93 out of 5 average rating, 219 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.

Superhost

An aerial view of the neighborhood showcases a mix of residential homes and palm trees, with the coastline visible in the background. The layout of the area highlights proximity to the beach, surrounded by greenery and well-maintained properties.

5 out of 5 average rating, 4 reviews

1009 Steps from the Beach! | by Brampton Park

Exclusively Managed By Brampton Park 200 Yards to Public Beach Access under half a mile to Atlantic Avenue 2 En-suite bedrooms with king beds and large living and dining area flooded with natural light Public Beach Access is 200 yards - Atlantic Avenue with unlimited dining and entertainment options is is under half a mile Upscale home in quiet residential street just steps to the ocean and close to Atlantic Avenue 2 En-suite bedrooms with king beds and large living and dining area.

A private backyard features a heated pool surrounded by sun loungers and a thatched tiki hut. Soft lighting enhances the serene atmosphere, while palm trees and a grassy area create a tranquil oasis. A stunning sunset sky adds color to the scene.

4.93 out of 5 average rating, 112 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.

4.98 out of 5 average rating, 44 reviews

Holiday 2BR Escape Walk to Atlantic Ave 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, 142 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!

Apartment in Delray Beach

5 out of 5 average rating, 14 reviews

Beach condo getaway!

Enjoy a stay at this peaceful and centrally-located place. Beautiful Corner Unit, full one bedroom with King bed. Walk to the beach and Atlantic Ave. Outdoor Heated Pool. The Best Location around and it includes free parking. Can rent weekly or monthly. Located next to the Ocean front Marriott and Opal Grand Hotel. Full kitchen with appliances. Stay here for a fraction of the price of the Marriott and enjoy this corner unit full one bedroom 675 square foot apartment.

4.87 out of 5 average rating, 223 reviews

A sandy path leads to the beach, bordered by lush green vegetation on either side. Wooden posts with ropes define the walkway, which opens up to a view of the blue sky and the distant ocean, creating an inviting coastal atmosphere.

Condo in Delray Beach

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.

4.99 out of 5 average rating, 101 reviews

Cottage 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.

5 out of 5 average rating, 7 reviews

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.

A private outdoor space features a sparkling swimming pool surrounded by lounge chairs and dining table. A large pink flamingo float rests in the water, while vibrant flowers frame the scene, adding color to the patio area.

4.91 out of 5 average rating, 236 reviews

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.

Popular amenities for Delray Beach rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 76 reviews

Relaxing Retreat | Pool + Near Beach & Atlantic Av

An aerial view showcases the beach cottage nestled in a lush, green landscape, surrounded by various residential properties. The expansive yard is highlighted, featuring a heated pool that glimmers under the sunlight, contributing to the property’s private and spacious atmosphere.

5 out of 5 average rating, 46 reviews

Dream Home steps to the Ocean with a Heated Pool!

4.97 out of 5 average rating, 137 reviews

The exterior of the house features a private pool surrounded by a spacious grassy area. A wooden deck with seating is situated at the back, providing a relaxing spot to enjoy the outdoors. Lush palm trees frame the setting, creating a serene atmosphere.

Home in Pompano Beach

•Floasis• Your private FL Oasis 5 min to beach!

A beautifully designed backyard features a heated saltwater pool surrounded by paver stone patio. Lounge chairs are placed along the poolside, accompanied by tropical greenery and decorative planters. A dining area with chairs is situated nearby, inviting relaxation and outdoor enjoyment.

4.98 out of 5 average rating, 48 reviews

SeaGrape Cottage

A spacious outdoor area features a saltwater pool surrounded by stone tiles. A spa with multiple jets is situated beside the pool. Comfortable lounge chairs and a dining area are positioned under an overhang, with well-maintained grass and tropical plants enhancing the environment.

4.97 out of 5 average rating, 34 reviews

A quiet, relaxing, hidden oasis.

A private heated saltwater pool is shown surrounded by lounge chairs and shaded umbrellas, set against a backdrop of tropical plants and a mural depicting vibrant flora. The pool area is enclosed with wooden fencing, enhancing the serene atmosphere.

5 out of 5 average rating, 33 reviews

FP Delray Delight: Saltwater Pool & Serene Oasis!

A private saltwater pool is surrounded by a spacious patio area with multiple seating options. An umbrella provides shade over a large dining table, while string lights add a subtle ambiance. Lush greenery frames the backyard, enhancing the serene outdoor setting.

4.96 out of 5 average rating, 25 reviews

5 Min to Beach ~ Heated Pool ~ Bikes Included

An aerial view captures the tranquil intracoastal waters with boats passing by. Lush greenery and palm trees frame the property, while several waterfront homes are visible in the background. The scene reflects a serene atmosphere characteristic of the East Delray Beach neighborhood.

4.96 out of 5 average rating, 23 reviews

Delray Beach Waterfront 4 Bedroom with Heated Pool

Condo rentals with a pool

4.94 out of 5 average rating, 110 reviews

The living room area features a dark blue sofa adorned with light-colored cushions. A neutral-toned area rug covers the floor. A kitchenette is visible in the background, with two bar stools positioned at a counter. A wall-mounted TV displays a city skyline.

Condo in Palm Beach

Beautiful 1 BR Condo Pool/Beach. Perfect Location!

4.93 out of 5 average rating, 116 reviews

Aerial view of the vibrant Fort Lauderdale coastline, showcasing golden sandy beaches lined with blue beach chairs and umbrellas. The iconic W Fort Lauderdale building is visible, along with modern structures and palm trees, under a partly cloudy sky.

Condo in Central Beach

Beachfront W Hotel Residence

Condo in Sunny Isles Beach

A sleek living area is highlighted by polished porcelain floors and reflective stretch ceilings. A grand piano adds elegance, while white sofas and a glass coffee table enhance the spaciousness. The open layout connects seamlessly to a modern kitchen in the background.

4.93 out of 5 average rating, 126 reviews

Luxury Beach & City View Condo 5 min walk to beach

4.95 out of 5 average rating, 207 reviews

A bright bedroom features a spacious bed dressed in white linens, complemented by soft lighting from bedside lamps. Large windows allow natural light, revealing decorative flowers outside. A cozy chair adds warmth, and a classic mirror enhances the inviting atmosphere of the room.

Condo in Palm Beach

Sensational Palm Beach Island with Grand Terrace

4.93 out of 5 average rating, 170 reviews

A comfortable living area is featured, with a light-colored sofa adorned with decorative pillows and beach-themed artwork on the walls. A wooden coffee table with a coastal design sits in front, complemented by a patterned area rug, creating a relaxed atmosphere.

Condo in Boynton Beach

Tropical Coastal Resort in Boynton Beach

4.94 out of 5 average rating, 185 reviews

An inviting living space is showcased with large floor-to-ceiling windows offering panoramic views of the ocean and city. A cozy sofa faces a wall-mounted television, complemented by a dining area and a breakfast bar, enhancing the open layout filled with natural light.

Condo in Singer Island

Ritz-Carlton Beach Penthouse by Guaranteed Rental

4.84 out of 5 average rating, 256 reviews

A serene outdoor space featuring a heated pool surrounded by palm trees and lounge chairs. A wooden dock extends into the intracoastal waterway, providing a picturesque view. The patio area includes shaded seating arrangements, creating an inviting setting for relaxation.

Condo in Pompano Beach

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

4.93 out of 5 average rating, 267 reviews

An open living and dining area is showcased, featuring a glass dining table surrounded by four chairs. A spacious sofa faces a large window with views of the cityscape, while a modern chandelier hangs above. A flat-screen TV is mounted on the wall, enhancing the contemporary design.

Condo in Central Beach

YOUR HOME by the Beach: TIFFANY HOUSE

Home rentals with a private pool

The living area features a cozy seating arrangement with a white sofa adorned with decorative pillows. A glass coffee table rests on a textured area rug, complemented by a wicker basket. Arched windows allow natural light to fill the space, showcasing lush indoor plants and tasteful decor.

Home in Southland Park

4.85 out of 5 average rating, 52 reviews

Elegant Getaway Near the Ocean in West Palm Beach

A spacious family room is accented by a large, dark sectional sofa with soft throw pillows. A marble coffee table sits at the center, while a stylish floor lamp stands nearby. Floor-to-ceiling glass doors provide a view of the lush greenery outside.