Vacation rentals with a pool in Gulf Stream

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Gulf Stream

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost

A serene outdoor space features a heated saltwater pool with soft blue lighting, complemented by lounge chairs nearby. Lush greenery surrounds the area, providing privacy, while a spacious patio with seating is visible in the background, all under a softly lit evening sky.

Home in Delray Beach

4.86 out of 5 average rating, 28 reviews

Prime Location • Saltwater Pool Retreat with Priva

Welcome to your Delray Beach oasis! This beautifully updated home offers a private saltwater pool, modern furnishings, and a separate fourth bedroom suite—perfect for families or groups looking to unwind in one of South Florida’s top coastal destinations. 🏖 Quick golf cart ride to Atlantic Ave & the beach 🧂 Saltwater pool with spacious outdoor lounge area 🛏 Private guest suite with its own en-suite bath 🍽 Fully equipped kitchen with indoor-outdoor dining spaces 📲 Smart home features + cura

Guest favorite

The outdoor area features a large heated pool surrounded by a spacious patio. Comfortable lounge chairs are positioned nearby, and lush palm trees add greenery to the scene. The white exterior of the house is visible in the background, with a clear blue sky overhead.

Home in Delray Beach

4.81 out of 5 average rating, 26 reviews

Island Estate: Pool, Tiki Lounge near Atlantic Ave

Fabulous Location! Minutes from Atlantic Ave. Make home sweet home at Palm Tree Island Estate! Large spacious bedrooms, and a huge second floor guest-suite/in-law suite, two kitchens, and a backyard lounge and beautiful heated pool that is fit to entertain the whole family! Located in a quiet, safe and beautifully maintained neighborhood of Delray Beach - only minutes from the Atlantic Ave, shopping and all that Palm Beach has to offer! PET FRIENDLY with fully fenced yard for them to explore!

Superhost

A large pool area features a heated pool surrounded by manicured grass. Multiple lounge chairs are positioned for relaxation under the sun. Tropical palm trees add greenery to the backdrop, complementing the serene atmosphere of the outdoor space.

Home in Delray Beach

4.91 out of 5 average rating, 118 reviews

Luxe Poolside Villas I

Welcome to Delray Beach’s stylish luxe villas. This pool home is perfect for a family or couple’s getaway. This modern villa offers a tranquil residential vibe alongside quick, easy access to the downtown areas and the popular Delray Beach. admire the crisp, contemporary decor or relax in your private patio equipped with BBQ grill and outdoor seating. Inquire about renting all 4 villas together. ALL 4 VILLAS HAVE THEIR OWN PRIVATE PATIO AND HAVE ACCESS TO THE 11,000 sq ft RESORT W/ AMENITIES.

Top guest favorite

A vibrant pink pool float with the text 'OUT OF OFFICE' is placed in the clear blue water of a private swimming pool. Additional pool floats in various colors are visible, creating a playful atmosphere. Lush greenery surrounds the pool area.

Home in Lake Worth

4.98 out of 5 average rating, 131 reviews

Tranquil Vibes ~ Pet Friendly Private Pool Home

Welcome to our cozy pool home with screened porch, deck w/ remote control lighting of cabana for evenings. Grill, tropical fruit trees, plants & private fenced yard. Coastal cottage decor mixing vintage finds in newly remodeled space. Neighborhood is peaceful w/ close drive to beaches, restaurants, golfing, parks & shopping. Each bedroom has cooling mattress pads & ceiling fans. Pets welcome! Beach chairs, cooler, bikes, beach umbrella, pool floats, yoga mat, games/books-.Long stays welcome

Guest favorite

The landscaped backyard features a heated pool surrounded by smooth stones and tropical plants. A hammock hangs between two palm trees, while a turquoise chair and patio seating offer spaces for relaxation. The setting is complemented by the warm glow of a sunset.

Home in Delray Beach

4.94 out of 5 average rating, 80 reviews

7min from Beach - Heated Pool, Hot Tub, EV Charger

This is the PERFECT Airbnb for a groups like big families or multiple couples. This listing is NOT shared and FULLY PRIVATE. This is a house that's divided into three private suites. Each have their own bedroom and bathroom. You are requesting to book all three! There is a beautifully landscaped backyard, HEATED pool, HUGE hot tub, & EV car charger. We are a short drive (~6min) to either the beach or Atlantic Ave - the place to be for bars and restaurants. Pack your bags and come relax!

Guest favorite

A private heated pool is surrounded by lush greenery and palm trees, fostering a relaxing atmosphere. The pool's bright blue water reflects sunlight, with pink inflatable floats gently bobbing on the surface. Comfortable lounge chairs are positioned nearby, offering a space for leisure.

Home in Delray Beach

4.92 out of 5 average rating, 183 reviews

Delray Beach-5 Bedr/4.5 bath*Heated Pool

Huge comfortable 5 bedroom, 3 ensuite & 2 half bathroom house in sought after Lake Ida area, Delray Beach, FL. Step into a relaxing, beach feel the moment you walk through the door. Enclosed backyard with large private heated pool. Beachtowels, towels, toiletries and all kitchen amenities included. Delray Public Beach: 2miles World renowned Delray Tennis stadium: 1.2 miles. Buzzing Atlantic Ave with restaurants, art galleries: 1 mile Pool loungers, umbrellas & grilling facilities outside.

Top guest favorite

A serene outdoor space features a pool surrounded by tropical landscaping and palm trees. A spacious patio includes seating areas, complemented by a pathway of laid bricks. Sunlight reflects from the clear water of the pool, creating a relaxed atmosphere.

Home in Delray Beach

4.93 out of 5 average rating, 204 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.

Top guest favorite

A clear view of the heated outdoor pool is presented, featuring built-in loungers on one side. The spacious patio is bordered by vibrant tropical landscaping and includes multiple seating areas. The white home is visible in the background, along with a second-floor balcony.

Home in Delray Beach

5 out of 5 average rating, 12 reviews

210 Walk to Pineapple Grove | by Brampton Park

Exclusively Managed By Brampton Park Heated Pool and Pet Friendly 4 Bedroom 3 Bathroom Delightful home, less than 1 mile to the Beach Modern, upscale downtown Delray home, fully renovated with all new furnishings as of July 2024. While this home is on a quiet residential street, the location is truly unbeatable - 1/4 mile to Pineapple Grove district that is bustling with restaurants, bars and cafes, and The Ray Hotel. Half a mile to Atlantic Avenue, and less than 1 mile to the beach.

Guest favorite

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.

Home in Delray Beach

4.95 out of 5 average rating, 20 reviews

Delray Beach Waterfront 4 Bedroom with Heated Pool

DIRECT INTRACOASTAL WATERFRONT! Watch the passing boat from the private backyard located in a quiet East Delray Beach neighborhood, across from the multi-million-dollar homes of Gulf Stream, Florida. Located within 3 miles from world famous Atlantic Ave in Downtown Delray Beach. Enjoy the top-rated restaurants, shops, nightclubs and the white sandy beach. Centrally located just north of Boca Raton and a short drive to either the West Palm Beach (PBi) or Fort Lauderdale (FLL) airports.

Guest favorite

Home in Delray Beach

4.95 out of 5 average rating, 95 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!

Guest favorite

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.

Home in Delray Beach

4.96 out of 5 average rating, 137 reviews

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!

Top guest favorite

A tranquil backyard features a sparkling saltwater pool surrounded by lush greenery and colorful landscaping. Two lounge chairs are positioned beside the pool, providing a place to relax. A white fence offers privacy while the clear blue sky enhances the serene outdoor space.

Home in Boynton Beach

4.95 out of 5 average rating, 60 reviews

Bright, open home w/ Pool, close to Delray & Beach

Luxury meets comfort at Boynton Beach East, close to downtown Delray, & beach. This home includes a spacious living room, fully-equipped kitchen, 2 bathrooms, & 3 cozy bedrooms that sleep 8. Outside, you'll find a private oasis complete with a fully fenced yard, patio, and grill. Take a dip in the pool, and relax with your friends and family. Enjoy nearby grocery stores & dining options, as well as easy access to PBI & FLL airports. Discover your next adventure!