Vacation rentals with a pool in Gulf Stream

4.9 out of 5 average rating, 208 reviews

An outdoor dining area is seen beneath a covered patio, featuring a table surrounded by black mesh chairs. Soft lighting illuminates the space, with a tranquil pool in view and a hammock hanging nearby, creating a peaceful atmosphere with surrounding greenery.

Home in Boynton Beach

CASA DE CONCHA - 3/2 POOL Home in Boynton Beach !

Conveniently located in central Boynton Beach with easy access to both I-95 and the FL Tpk, and only 4 miles to the beach, this charming and tastefully appointed 5 * rated 3/2 pool home offers exceptional comfort (new mattresses, loaded with amenities), leisure (private enclosed pool, outdoor dining area, fire pit), AND utility (fully equipped kitchen, grill, home office) for families and business travelers alike! Come stay with us and enjoy the benefits of an EXPERIENCED SUPERHOST-managed home!

Superhost

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

4.83 out of 5 average rating, 103 reviews

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!

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.

Vacation home in Delray Beach

5 out of 5 average rating, 5 reviews

Intracoastal Waterfront Delray Home w/Boat Dock

DIRECT INTRACOASTAL WATERFRONT HOME FOR RENT in Delray Beach! Private gated single-family home with a heated pool, private dock, boat lift & covered patio. Watch the passing boats from the private backyard located in a quiet East Delray Beach neighborhood, across from the multi-million-dollar properties of Gulf Stream, Florida. Family-friendly neighborhood for walking the dog, jogging, or biking. Only minutes from the Beach, restaurants, shops & entertainment on Atlantic Ave in Delray.

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, 119 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!

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.

4.91 out of 5 average rating, 148 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!

A heated pool invites relaxation, surrounded by a serene yard with tropical palm trees. Colorful floats rest on the water's surface, while sun loungers and conversation chairs provide ample seating for enjoying the outdoors.

4.94 out of 5 average rating, 136 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

Superhost

5 out of 5 average rating, 3 reviews

3 Br Heated Pool Villa near Downtown Delray Beach

Escape to this stylish 3BR, 2BA coastal villa just minutes from downtown and the beach! Enjoy a private fenced yard with a sparkling pool, outdoor dining, and BBQ grill. Inside, relax in bright open spaces with a modern kitchen, stainless appliances, and dining for six. Bedrooms feature hotel-quality linens and Smart TVs. Includes free beach passes, washer/dryer, and board games. Minutes to downtown’s shops, galleries, and restaurants in “America’s Most Fun Small Town.”

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.

4.95 out of 5 average rating, 139 reviews

Waterfront Htd Pool, Spa, Billiards, Lanai, Canal

🌴 Relax at this luxury waterfront Delray Beach retreat in Delray Beach, featuring a heated pool & spa, private dock, screened porch with string lights & Smart TV, pool table, BBQ, and canal views. Bright open living and flexible sleeping for up to 10 guests make it perfect for families and groups seeking comfort, space, and true South Florida relaxation. Message us today and enjoy waterfront luxury, sunshine, and relaxation — all in one exceptional stay. 🌴☀️

An aerial view showcases a modern home painted in soft turquoise, surrounded by lush greenery. A sparkling pool is framed by neatly manicured grass, and two umbrellas provide shade over outdoor seating. The inviting atmosphere is complemented by palm trees and a pop of vibrant colors.

4.96 out of 5 average rating, 100 reviews

The Dream Delray/ 4 BR En-suite Pool Home

Dreams Delray is a modern 4 bedroom 4 1/2 bathroom (4 Bedroom En Suites) heated pool home which is a 10 minute walk to "The Ave,” Delray Beach's popular downtown venue, and a short 5 minute drive to our famous sandy beaches. It has everything you can ask for the perfect family vacation or a small getaway to sunny Florida. The home offers a top chef kitchen open floor plan, surround sound and a wonderful view of the pool from just about every part of the house.

4.98 out of 5 average rating, 54 reviews

A private heated saltwater pool is set within a landscaped yard, featuring a smooth stone surround. Two lounge chairs are positioned at the pool’s edge. Colorful floats are invitingly placed on the water, and lush greenery borders the area, providing a serene atmosphere.

Home in Boynton Beach

Dinner on us, beach pass, saltwater pool. All NEW!

Private oasis, salt water heated pool, cozy, and clean This home is off of 95 & between Delray Beach's famous Atlantic Avenue & West Palm Beach's nightlife. Great for a girl's weekend, snowbirds, kid friendly, & cozy. The backyard is paradise! Kickback and relax by the private heated saltwater pool, Enjoy a day at the beach with the homeowner's beach pass and free parking. Walk to dinner at multiple locations. Mostly, enjoy this little piece of paradise.