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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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A private screened-in pool area features a crystal-clear pool bordered by a wooden deck. A hammock hangs nearby, surrounded by lush greenery, providing a serene environment for relaxation. Dappled sunlight creates a tranquil atmosphere across the space.

Home in Boynton Beach

4.91 out of 5 average rating, 204 reviews

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!

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

4.99 out of 5 average rating, 134 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

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, 82 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!

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, 210 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.

Home in Delray Beach

4.95 out of 5 average rating, 103 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!

A modern living area features a light gray sectional sofa, a simple wooden coffee table, and a colorful area rug. Natural light fills the space through large windows, creating a bright and airy atmosphere.

Home in Boynton Beach

4.88 out of 5 average rating, 34 reviews

Modern renovated oasis home with private pool

Escape to your beach oasis in the heart of Boynton Beach, where modern luxury meets vibrant tropics. Less than 5 minutes from shopping centers, restaurants, Ocean Ridge Beach, and Lake. Features include a large inground pool, spacious rooms, a fully equipped kitchen, onsite laundry and dryer unit, yard games (cornhole), and a gigantic living space! Whether you're seeking adventure or simply craving a peaceful retreat, our home offers the perfect blend of convenience and serenity.

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, 142 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!

A welcoming living space features two sofas, complemented by a pair of round wooden tables. Natural light enters through the windows, illuminating the neutral-toned decor. A ceiling fan is present overhead, while bar seating is visible in the background near the kitchen area.

Apartment in Delray Beach

5 out of 5 average rating, 5 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.

A private pool glimmers under clear skies, surrounded by a screened enclosure. Two chairs are positioned neatly by the water's edge, providing a place to relax. The spacious patio includes a dining table visible in the background, framed by lush greenery.

Home in Boynton Beach

4.93 out of 5 average rating, 134 reviews

Modern, spacious 4-Bedroom with private pool

Feel peace + calm in this spacious, serene space. Enjoy the gentle lapping of your own private pool & crickets, or fill the large, open space with laughter, family and friends. Eat indoors or out; the patio & pool are fully screened. Cool off inside without missing out; you'll still see the pool and backyard from the kitchen, dining area, living room, and master bed. The 15' couch seats 8 comfortably in front of the 58" 4K TV. 4 bedrooms, 2 baths.

Lush green vegetation is bordered by a wooden fence running along the pathway. Tall palm trees are visible against a bright blue sky, while a windmill structure can be seen on the horizon, adding a charming detail to the coastal scenery.

Condo in Delray Beach

4.84 out of 5 average rating, 161 reviews

Retro charm condo steps from beach & Atlantic Ave

Discover Delray Beach’s best-kept secret: our vintage-style 1-bedroom, 1-bath hideaway. Tucked just off Atlantic Avenue behind the luxurious Opal Grand hotel, this charming king-bed retreat is perfect for a beach escape. Less than a 2-minute walk to Delray’s sandy dunes, it’s both near the vibrant bars and restaurants and peacefully hidden away. This modern, cozy space offers all the comforts of home in a vacation-style setting.

A spacious outdoor pool area features a bright yellow umbrella providing shade over lounge chairs arranged around the water. Lush tropical plants line the perimeter, creating a secluded atmosphere for relaxation and enjoyment.

Home in Delray Beach

New! Luxury Tropical Oasis - Delray Beach

Escape to this stylish 3-bedroom, 2-bath retreat just minutes from the beach and iconic Atlantic Avenue. With designer interiors, a fully stocked kitchen, luxury outdoor seating, and thoughtful family-friendly touches, this Delray Beach gem is the perfect blend of comfort and convenience. Enjoy complimentary concierge service, plush amenities, and everything you need for an effortless and unforgettable stay in South Florida.

A spacious backyard is showcased, featuring a large heated pool surrounded by lounge chairs and tropical landscaping. Outdoor seating is provided under a covered patio, with a barbecue grill visible in the background. Bright blue skies and lush greenery enhance the inviting atmosphere.

Home in Delray Beach

4.93 out of 5 average rating, 113 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!

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Popular amenities for Gulf Stream rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

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.

Home in Delray Beach

4.94 out of 5 average rating, 118 reviews

Waterfront Htd Pool, Spa, Pool Table, Lanai, Canal

The aerial view displays a heated pool surrounded by lounge chairs and yellow umbrellas. The pool area features two colorful pool floats. Enclosed by lush greenery, the exterior space offers privacy and a relaxing environment for guests.

Home in Delray Beach

4.97 out of 5 average rating, 106 reviews

Heated Pool | Delray Beach Honey Hole

Home in Delray Beach

5 out of 5 average rating, 46 reviews

Dream Home steps to the Ocean with a Heated Pool!

The exterior of the home is surrounded by lush greenery and palm trees, featuring a spacious driveway that leads to a large garage. Natural light filters through the trees, creating a calm and inviting entrance to the property.

Home in Boynton Beach

5 out of 5 average rating, 8 reviews

Cozy 3BR Boutique Home • Heated Pool • Near Beach

Top guest favorite

A spacious backyard features a large heated pool surrounded by travertine decking. Lounge chairs and a dining area are positioned nearby, while lush landscaping and palm trees provide a tropical feel. The white exterior of the house complements the serene outdoor space.

Home in Flamingo Park

4.99 out of 5 average rating, 105 reviews

Luxe Home w/ Stuffning Pool Near Beach + Downtown

Top guest favorite

A heated saltwater pool is framed by lounge chairs under large umbrellas, creating a comfortable outdoor space. Lush tropical landscaping enhances the privacy, while a vibrant mural featuring flamingos adds a colorful touch to the scene. The sky exhibits shades of purple and blue as dusk approaches.

Home in Delray Beach

5 out of 5 average rating, 32 reviews

FP Delray Delight: Saltwater Pool & Serene Oasis!

A spacious backyard features a newly built saltwater pool accompanied by lounge chairs. A shaded umbrella offers relief from the sun. A hammock is positioned nearby for relaxation. The well-maintained lawn surrounds the area, enhancing the inviting outdoor space.

Home in Boynton Beach

4.96 out of 5 average rating, 73 reviews

Large Heated Pool - Family Friendly Private BBQ

An outdoor seating area is arranged around a fire pit, surrounded by lush landscaping. A well-lit pool glows blue in the evening light. Dining and lounging furniture is placed strategically, with an umbrella providing shade for an outdoor kitchen and bar area in the background.

Home in Boynton Beach

4.98 out of 5 average rating, 62 reviews

Dip n' Sip Oasis! Heated pool, minutes from beach

Condo rentals with a pool

An aerial view captures the vibrant beachside scene, featuring a long stretch of sandy beach lined with beach chairs and umbrellas. The clear blue water contrasts with the white sand and lively resort buildings, showcasing a scenic blend of oceanfront activity and urban landscape.

Condo in Central Beach

4.93 out of 5 average rating, 113 reviews

Beachfront W Hotel Residence

A clear view of a swimming pool surrounded by lounge chairs is framed by tropical palm trees. The condo building rises in the background, complementing the calming atmosphere of the outdoor area.

Condo in Boynton Beach

4.92 out of 5 average rating, 158 reviews

Tropical Coastal Resort in Boynton Beach

A large multi-story resort structure is surrounded by lush palm trees and tropical landscaping. A swimming pool extends in the foreground, featuring lounge chairs arranged along its edge, reflecting a clear blue sky above.

Condo in West Palm Beach

4.91 out of 5 average rating, 153 reviews

Marriott Ocean Pointe Guest Room/Studio

Top guest favorite

A dining area offers a clear view of the Intracoastal Waterway through large windows. The scene captures a passing boat, surrounded by palm trees and waterfront properties. A circular table is visible, accompanied by elegant chairs, creating a serene dining atmosphere.

Condo in Pompano Beach

4.99 out of 5 average rating, 132 reviews

Waterfront Condo ON the Intracoastal. Great views!

A neutral-toned master bedroom presents a queen bed layered with plush pillows and a soft throw. Flanking the bed are two bedside lamps, providing a gentle glow. A decorative piece featuring fish artwork adorns the wall, complemented by a window with horizontal blinds.

Condo in Pompano Beach

4.85 out of 5 average rating, 242 reviews

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

Condo in Palm Beach

4.91 out of 5 average rating, 329 reviews

🌞Palm Beach🌴view studio by the🏖 w/parking⚡wifi

Top guest favorite

A sparkling blue pool is surrounded by lounge chairs and umbrellas, set amidst tropical palm trees. The pool area is enclosed by a low fence, with a view of nearby buildings and the street. Bright orange accents on the chairs enhance the inviting space.

Condo in Deerfield Beach

4.92 out of 5 average rating, 144 reviews

Spacious Deerfield Beach Condo

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

4.93 out of 5 average rating, 260 reviews

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 West Palm Beach

4.85 out of 5 average rating, 52 reviews

Elegant Getaway Near the Ocean in West Palm Beach

A private pool is set against a backdrop of lush greenery, featuring a gently sloped entry. The surrounding patio is spacious, providing ample room for relaxation and sunbathing. A covered area offers shade and protection from the sun, enhancing outdoor enjoyment.

Home in Boca Raton

4.78 out of 5 average rating, 41 reviews

Boca Beauty - Stylish Home with Pool

A serene pathway lined with tropical plants leads to a stone table, surrounded by lush greenery and vibrant palms. The path is paved with bricks, creating a welcoming entrance to a private garden area.

Guesthouse in Flamingo Park

4.97 out of 5 average rating, 177 reviews

Tropical Cabana with Pool in West Palm Beach

Top guest favorite

A heated saltwater pool is framed by lush greenery, providing a sense of privacy. The pool features a decorative wall at one end, adding an elegant touch. The surrounding patio offers a clean, open space for relaxation.

Home in Flamingo Park

4.96 out of 5 average rating, 176 reviews

Soak up the Beachy Vibe at a Vibrant Poolside Paradise

The exterior of a single-story home is framed by palm trees and manicured landscaping. A paved pathway leads to the entrance, featuring a round window and a decorative door. The white garage door is visible on the right, and blue skies create a bright backdrop.

Home in Lake Worth Beach

4.78 out of 5 average rating, 9 reviews

Gorgeous Lake Worth Beach House

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