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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Guest favorite

An aerial view captures the serene waterfront neighborhood, showcasing a winding waterway bordered by lush greenery and luxury homes. The proximity to the ocean is evident, with several pools and dock spaces visible among the residences.

Home in Delray Beach

4.97 out of 5 average rating, 87 reviews

Direct INTRACOASTAL Waterfront 3BR - Pool & Dock

Relax on your private backyard patio with the famous south Florida intracoastal waterway as your back drop. Sip cocktails & watch the million dollar yachts sail by or throw a fishing line off the dock. This is the BEST Florida home for anyone who loves waterfront living. Sunbathe in the heated pool or fire up the the outdoor kitchen grill or fire pit. Enjoying the outdoor salt life at your very own private resort is what this home is all about. No parties, events or get togethers permitted.

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

Superhost

Home in Delray Beach

5 out of 5 average rating, 4 reviews

Downtown Delray Luxury Pool Villa

Luxurious 4 bedroom/4 bath home in the heart of Downtown Delray, 3 blks from Pineapple Grove, short walk to Atlantic Ave for boutiques, fine dining & beautiful beaches. Indoor/outdoor living w/ lap pool, fire pit & outdoor living space w/TV, Sonos & remote-controlled screens. Downstairs: expansive master retreat, guest bedroom, game room, gourmet kitchen, dining area, laundry room, powder room & family room . 2 bd w/ensuite bathrooms upstairs plus loft. 2-car garage w/electric charging station.

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

4.79 out of 5 average rating, 24 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, 79 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, 200 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

Home in Boynton Beach

5 out of 5 average rating, 15 reviews

906 Stunning views of Lake Eden | By Brampton Park

Exclusively Managed by Brampton Park Heated Pool, Hot tub & Pet Friendly Private Resort style home with endless views over Lake Eden Newly built and furnished February 2024 - all the reviews prior to this time are from the previous home. Ideal location - right on the border of Delray Beach - very short drive to Atlantic Ave. Located on a quiet cul de sac Expansive lawn overlooking Lake Eden. Backyard features a hot tub, large fire pit, covered gazebo and swings, all overlooking Lake Eden

Guest favorite

Home in Delray Beach

4.95 out of 5 average rating, 93 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

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.

Home in Delray Beach

4.92 out of 5 average rating, 134 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!