House holiday rentals in Highland 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 🏖

4.83 out of 5 average rating, 100 reviews

The kitchen features a modern design with white cabinetry, stainless steel appliances, and a spacious island. A wooden beam accents the ceiling. Natural light enters through a window and sliding glass door, which opens to the outdoor space. A dining table with chairs is positioned nearby.

Home in Highland Beach

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!

4.9 out of 5 average rating, 145 reviews

Family & Pet Friendly NEAR Beach/AtlanticAve/FAU

Central Location - Quick drive to the beach! ▪️5 min. drive (1.8 miles) to the Beach ▪️3 min. drive (3/4 mile) to Downtown Delray - Restaurants, shops, bars and night life ▪️5 min. drive to the nearest grocery store - Publix, Bedner's Farm Fresh Market ▪️7 min. drive (2.7 miles) to Target/Trader Joe's ▪️2 min. drive to the Historic Swinton Ave ▪️2 min. drive to the Delray Tennis Center ▪️20 min. drive (18 miles) to West Palm Beach Airport ▪️35 min. drive (32 miles) to Fort Lauderdale Airport

An outdoor seating area under a thatched roof features comfortable lounge furniture arranged around a gas fire table. A flat-screen TV is mounted nearby. The inviting pool is visible in the background, surrounded by tropical landscaping and sun loungers.

4.99 out of 5 average rating, 89 reviews

Paradise Palms our tropical oasis in Delray/Boca!

Welcome to Paradise Palms, our tropical oasis! This 3 bedroom, 2 bath home is a perfect getaway to relax and unwind. Enjoy the beautiful pool, hot tub, and tiki hut with gas fire table, bar and TV. There is a wood fire pit, hammock, 4 bikes, 4 beach chairs, snorkeling gear, ping pong and plenty of outdoor games. The interior has all of the comforts of home with a fully equipped kitchen, TV in every room. The property is conveniently located near the beach, downtown Delray, and Boca Raton.

The private pool area showcases a sparkling blue pool, complete with a spa and sun loungers beneath vibrant red umbrellas. Lush greenery and tranquil waterfront views create a serene atmosphere, inviting relaxation and enjoyment under a bright blue sky with fluffy white clouds.

4.94 out of 5 average rating, 126 reviews

Waterfront Htd Pool, Spa, Pool Table, 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!

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, 217 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.

A charming casita is set against a lush green lawn, framed by vibrant foliage. The entrance features light blue accents and a small seating area with two white chairs, inviting relaxation. Sunlight casts gentle shadows, enhancing the welcoming appearance of the home's exterior.

4.93 out of 5 average rating, 136 reviews

CASITA DELRAY (314 SW 2nd Street)

Charming Renovated 2 Bedroom “Casita” Close to Downtown Delray Beach!! Beautifully Decorated with thoughtful details throughout Quality Mattresses, Bedding, Plush Pillows,, & Towels, 2 Beach Cruiser Bicycles for a quick ride downtown or to the beach 3 Beach Chairs / Beach Umbrella / Beach Towels / Yoga Mat Provided Private Fenced Backyard with Weber BBQ / Table and Chairs for Outdoor Dining / Hammock. Close to Downtown....Restaurants, Bars, Shoppes, Nightlife and award-winning BEACHES ;)

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.

4.94 out of 5 average rating, 108 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!

4.94 out of 5 average rating, 102 reviews

A clear blue pool occupies the outdoor area, surrounded by a wooden fence and shaded seating under umbrellas. The interior includes a dining table set for four, a modern living room with a television and ample seating, and a spacious kitchen with stainless steel appliances and white cabinetry.

Home in Deerfield Beach

Real Big 1BR/BA Unit; Pool; Near Beach

Forget your worries in this spacious and serene, modernized space. An oversized private unit. Self check-in. Full kitchen. Full bathroom. Speedy wifi. 2 Roku tvs. Washer and dryer inside. Need to cool down? Take a swim in the large pool or travel 5 mins (1.5 miles) up to the beautiful Deerfield Beach ocean. Eateries and shops galore in the immediate area, walking distance. Parking limit: 2 vehicles. Book now & enjoy. You won’t regret this stay.

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, 230 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.

A spacious living area features natural wood beams overhead and large windows allowing natural light to fill the space. A comfortable sectional sofa with colorful cushions is positioned next to a modern coffee table. A dining table is visible, accompanied by mid-century style chairs.

4.82 out of 5 average rating, 106 reviews

2 Bed Cottage walk to Pineapple Grove Ave & Beach

Keep it simple at this peaceful and centrally-located place. This remodeled cottage features a brand new kitchen and bathroom. Spend your days either relaxing in the quiet patio surrounded by greenery or walk to Pineapple Grove or the Ave for a drink or bite to eat. Enjoy time at the beach with your friends and family and in the evening take a stroll through the historic district soaking in the real culture of Delray Beach.

An outdoor covered patio features seating arrangements with comfortable furniture, complemented by decorative cushions. A fan hangs from the wooden ceiling, providing a cooling breeze. The lush backyard offers views of a large heated pool surrounded by tropical landscaping.

4.93 out of 5 average rating, 116 reviews

Heated Pool! 1 Mile To Beach & Atlantic Avenue!

COZY COTTAGE STYLE HOME W/COASTAL FINISHES, BEAUTIFULLY FURNISHED IN THE HEART OF DELRAY BEACH. THIS BEAUTIFUL HOME INCLUDES 3 BEDROOMS & 2 BATHROOMS & A LARGE HEATED POOL! 1 MILE TO THE BEACH, ATLANTIC AVENUE, WATER-SPORT ACTIVITIES, FINE AND CASUAL DINING, NIGHT LIFE & UPSCALE SHOPPING & MINUTES TO BOCA RATON. BEAUTIFUL COVERED PATIO TO GRILL AND RELAX ON SOME LOUNGE CHAIRS WHILE OVERLOOKING THE LARGE HEATED POOL!

Popular amenities for Highland Beach house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A dining area is highlighted by a large table with light-colored wood and comfortable chairs. Large windows provide ample natural light and a view of the outdoor space, featuring a pool and lounge chairs under shaded umbrellas.

5 out of 5 average rating, 25 reviews

Villa Sunshine - Luxury Home, Heated Pool

A spacious pool area is surrounded by a well-maintained yard, featuring vibrant green foliage. Two blue umbrellas provide shade over a dining table set for six, while four lounge chairs await sunbathers. A whimsical flamingo float is resting on the water, adding a playful touch.

4.93 out of 5 average rating, 146 reviews

DWTN Delray Pool Home | FREE Beach Cabana service

A private outdoor space features a heated saltwater pool surrounded by a manicured lawn. Lounge chairs and a patio set are placed nearby, while lush tropical plants and palm trees create a serene atmosphere. A pink float adds a pop of color to the pool.

4.98 out of 5 average rating, 90 reviews

EAST BOCA RATON 1MILE TO BEACH! PRIVATE POOL HOME!

4.88 out of 5 average rating, 100 reviews

3 Bed, 3 Bath. Heated pool. 1 mile from beach!

5 out of 5 average rating, 6 reviews

A serene backyard scene features a clear blue pool, surrounded by palm trees and elegant lounge chairs. A shaded gazebo offers a space for relaxation. The pool area overlooks the tranquil waterway, enhancing the natural beauty of this private outdoor retreat.

Home in Boynton Beach

*NEW*10min to Atlantic Ave Delray | Walk 2 Beach |

An inviting living area features a large sectional sofa adorned with colorful cushions, paired with a wooden coffee table. High, beamed ceilings and ample natural light create an open atmosphere. A staircase leads to the upper level, while a dining table awaits nearby, enhancing the communal feel.

5 out of 5 average rating, 34 reviews

Delray Family Pool Escape, Near Beach

A refreshing pool area is surrounded by tropical palm trees and vibrant greenery. Comfortable seating is available around the pool, and a water slide adds an element of fun. Potted plants enhance the outdoor environment, creating a serene space for relaxation.

5 out of 5 average rating, 8 reviews

Boca Raton Private Oasis

The outdoor space features a heated pool surrounded by tropical landscaping. Cozy seating arrangements consist of dark wicker furniture with decorative cushions. Warm string lights illuminate the area, enhancing the inviting ambiance as evening approaches.

4.95 out of 5 average rating, 38 reviews

Paradise Pointe East Delray Pool Home

Weekly house rentals

5 out of 5 average rating, 20 reviews

Home in Boynton Beach

Sunny Retreat in Boynton Beach

5 out of 5 average rating, 3 reviews

Delray’s Zen Paradise!

5 out of 5 average rating, 3 reviews

3/2 Home with Pool & Backyard in East Delray

A cozy living area is highlighted by a large sectional couch adorned with decorative pillows. A striped rug adds color to the tiled floor. In the background, a fully equipped kitchen is visible, framed by natural light from the windows.

4.94 out of 5 average rating, 49 reviews

Casa Rosa Pineapple Grove - Your Lush Garden Oasis

4.93 out of 5 average rating, 14 reviews

An open-concept living area features a modern kitchen with wood cabinetry and stainless steel appliances. A dining area with bar stools offers a casual eating space. Comfortably arranged seating, including light armchairs and a neutral area rug, creates an inviting space with natural light from large windows.

Home in Boynton Beach

New Upscale Luxury Finish Home 8m to Beach

A bright and airy open-concept living space features light-colored wood flooring and modern furnishings. The dining area showcases a white table surrounded by woven chairs. A spacious kitchen can be seen in the background, with sleek cabinetry and a large island. Natural light pours in through multiple windows.

5 out of 5 average rating, 20 reviews

Stunning 3 BED modern pool home by the Beach

A well-maintained backyard features a pristine swimming pool surrounded by a spacious patio. Sun loungers are positioned on the grass, and lush greenery provides a sense of privacy. A shaded seating area is visible in the background, adding to the outdoor relaxation space.

4.97 out of 5 average rating, 33 reviews

Boca Gem: Pvt Pool & Ocean Bliss

5 out of 5 average rating, 19 reviews

A modern pool area features a sparkling blue swimming pool surrounded by a spacious patio. Lounge chairs are arranged for relaxation under large umbrellas. Lush greenery and palm trees provide a natural backdrop, enhancing the outdoor setting for leisure and enjoyment.

Home in The Cove

Paradise Cove: Heated Pool and Modern Luxury

Private house rentals

A living area features large windows that provide views of the waterfront and lush greenery. Comfortable seating is arranged around a coffee table, with decorative pillows adding texture. A flat-screen TV sits on a media console, with a ceiling fan overhead contributing to the airy atmosphere.

4.96 out of 5 average rating, 23 reviews

Waterfront 3BR! Spacious Dock, King Bed, BBQ

4.95 out of 5 average rating, 75 reviews

Relaxing Retreat | Pool + Near Beach & Atlantic Av

5 out of 5 average rating, 9 reviews

A modern living area features a large sectional sofa and an inviting cream-colored ottoman. Natural light floods the room through expansive glass doors, offering views of the waterfront and lush greenery outside. A sleek entertainment unit complements the contemporary design.

Home in Deerfield Beach

Zen Haven Intracoastal Escape

4.93 out of 5 average rating, 45 reviews

Home in Deerfield Beach

Sunseeker at Deerfield Beach

5 out of 5 average rating, 5 reviews

Luxury Tropical Family Oasis

4.83 out of 5 average rating, 48 reviews

East Delray BEACH/Atlantic Ave/ family

A spacious living area features a large sectional sofa oriented towards a flat-screen TV, with natural light streaming in through large windows. A cozy dining table for four is positioned next to the sofa, complemented by indoor plants and playful decor elements.

4.91 out of 5 average rating, 82 reviews

3BR • 1 Mile to Beach • Arcades • Games • Near FAU

An open living area features a comfortable seating arrangement with gray sofas and patterned armchairs. Large windows allow natural light to fill the space, offering a view of the outdoor area. A modern kitchen is visible in the background, equipped with sleek appliances and bar seating.