
Vacation rentals with a pool in Gulf Stream
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Gulf Stream

Total vacation rentals
Explore 50 vacation rentals in Gulf Stream

Nightly prices starting at
Gulf Stream vacation rentals start at R 990 ZAR per night before taxes and fees

Verified guest reviews
Over 480 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
50 of Gulf Stream vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Gulf Stream rentals

4.6 Average rating
Gulf Stream stays receive an average rating of 4.6 out of 5 from guests
Top-rated rentals with a pool in Gulf Stream
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Luxe Private Pool & Spa*2 King Bds*Heart of Delray
🌴 The Villa at Serenity Palms 🌴 *Escape to your own private retreat in the heart of Delray. *Enjoy a private saltwater pool, spa, and outdoor spaces designed for carefree relaxation. *Tucked into a quiet, charming neighborhood, steps from town and the beach, this beautifully designed villa offers a rare blend of walkability, privacy, and elevated comfort. *Thoughtfully curated, the home blends high-end finishes with a warm, livable feel. Guests describe it as a “boutique hotel only better.”

3535 | Waterfront | 4bd | Pool | by DelrayNightly
DELRAY NIGHTLY VACATION RENTALS proudly presents Oasis Palms House. A 4-bedroom, 3-bath villa on the north end of Lake Ida, and minutes from downtown Delray. Includes a 6-passenger golf cart. Features two king-bed primary suites, connecting to a chef-ready kitchen, a living room with 85" Smart TV, a Sonos sound system, and dining for 8. Enjoy a heated pool, covered lanai, fire pit, and direct lake access, turning the outdoors into a primary living space. Paddleboards and kayaks are included.

Large Heated Pool - Family Friendly Private BBQ
Welcome to our renovated family-friendly home centrally located in the heart of Boynton Beach, Florida. This home is perfect for families seeking a spacious and friendly retreat. With 3 bedrooms, 4 beds, 2 full bathrooms, and a fully stocked kitchen and laundry area, we've ensured a relaxing and convenient stay for up to 8 people. Take a dip in our newly built saltwater HEATED pool or relaxing in the hammock's backyard, along with a bbq grill and cornhole set for you and your guests to enjoy.

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.

Private|Stylish|Pool|Yard|Parking|Pets|Near Ave
Welcome to your stylish 3BR/2BA retreat that is perfect for families, friends, or couples looking to unwind and enjoy “The Village by the Sea”—just minutes from beaches, dining, and nightlife. Lounge in your private yard with a heated saltwater pool—or explore downtown Delray. ✔ 3 Cozy Bedrooms ✔ Open Living & Dining ✔ Stocked Kitchen ✔ Heated Saltwater Pool & Yard ✔ Grill, Lounge Chairs, Outdoor Dining & Games ✔ Smart TVs ✔ Fast Wi-Fi (Remote Work Ready) ✔ Washer/Dryer ✔ Free Parking

Htd Pool/Spa, Putt Green & G. Tee- Walk to The Ave
This exquisite, fully renovated Delray Beach villa is a golfer’s dream! Just blocks from lively Atlantic Ave and 1.3 miles from the beach, it features a private 3-hole putting green, Golden Tee arcade game, and a heated saltwater plunge pool & spa with color lights, jets, and bubbles. Fire up the grill and dine al fresco beneath charming bistro lights. Enjoy stylish interiors, vibrant nightlife, and Freebee golf cart rides (or walk) to The Ave’s restaurants, shops, and beach. Sleeps 8.

Jungle Heated Salt Pool, Private, Near Beach
Welcome to the Jungle House – Your Private Salt Pool Oasis Unwind in your own tropical retreat just 5 minutes from the ocean. Hidden in a quiet Boynton Beach neighborhood, this 3-bedroom, 2-bath family-friendly home blends safari-inspired design with lush jungle gardens and a heated saltwater pool you’ll never want to leave. Whether you’re relaxing under the trees, grilling dinner by the pool, or biking to the beach, the Jungle House offers the perfect mix of adventure and privacy.

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!

The Dream 4 BR En-suite Pool Home close to beach
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.

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!

Waterfront 3BR| Marina Views| Delray Beach
Stunning marina-facing residence in the heart of Delray Beach. Walk to boutique shops, restaurants and bars. This gorgeous home offers luxury finishes, modern design and a personal meet-and-greet experience. Wake up to breathtaking marina and yacht views from your private furnished terrace. Note: owner may occasionally stay in a fully separate detached apartment with its own private entrance and shared driveway, with no impact on your stay.

Heated Pool, Hot Tub, Pickleball & Putting Green
Discover your own piece of paradise just minutes from Delray Beach’s vibrant Atlantic Avenue and pristine shoreline. This modern 4-bedroom home is ideal for large families, groups, or corporate retreats. Lounge by the private heated pool, unwind in the hot tub, challenge friends on the pickleball court or putting green, catch your favorite shows on a TV in every bedroom, or gather for a memorable feast in the state-of-the-art kitchen.
Popular amenities for Gulf Stream rentals with a pool
House rentals with a pool

Luxury Delray Beach 4/3 Pool Spa 2 King Masters

Elegant & Glamorous way private pool with heater

Lala’s Art Beach House Escape

Delray Getaway- Mid-Century Oasis by the Sea!

Heated Pool BBQ Grill 3 Bedroom 4 min Beach&Delray

Luxe Hideaway with Pool & Garden

3144 Spotless Modern | By Brampton Park

Luxury 3brm lakehouse. Pool, Tiki , golf & Fishing
Condo rentals with a pool

Beautiful 1 BR Condo Pool/Beach. Perfect Location!

Fantastic Location - Walking distance to Beach!

Tropical Coastal Resort in Boynton Beach

Luxe King Suite -valet parking-near beach

ON CANAL! Pool+Walk to BEACH! Boat Watch! 2b/2b

Charming studio just by the beach & Atlantic Ave

Spacious Deerfield Beach Condo

Landex @ Dover House 1 bedroom 1 bath
Other vacation rentals with a pool

Tropical oasis with amazing tiki, pool

Dazzling Delray

Blissful Boynton Escape

Cozy Fireplace | Pro Furnished | Fully Stocked

237 | Sleeps 8 | Pool | Putting | by DelrayNightly

5 Min to Beach - Heated Pool - Bikes Included

Walker's Tropical Oasis

Delray Oasis with pool. 2 mi to Atlantic/Beach
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- Rapids Water Park





