Vacation rentals with a pool in Gulf Stream

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.

231 NEW - Heated Pool & Tropical Oasis - Near Ave

Delray Nightly is proud to present The Harmony Palms House, a newly renovated, luxurious Delray Beach vacation rental featuring a private heated pool, tiki hut lounge, and tropical backyard. Enjoy king bedrooms, fun games, high-speed Wi-Fi, and covered outdoor dining. Just minutes from Atlantic Avenue, the beach, and downtown, with FREEBEE shuttle access for easy, eco-friendly transportation, this home is perfect for families, friends, or couples seeking stylish, relaxing South Florida getaway.

Luxury beach house on A1A

Luxurious 3-Bedroom Home on A1A with Private Pool & Tiki Bar Welcome to your perfect getaway steps from the beach. It’s an ideal mix of comfort and entertainment, each bedroom featuring en suite bathrooms for ultimate privacy. The den converts to a 4th bedroom, with full-size Murphy bed and full bathroom. Step outside into the private oasis! Refreshing pool and tropical tiki hut for sipping drinks or grilling on the barbecue. It’s a perfect spot to relax and enjoy the peaceful surroundings.

Delray Getaway- Mid-Century Oasis by the Sea!

Our comfy, coastal MidCentury home sits on a large 7,850sf lot conveniently located at the end of a dead end street. Our backyard is layered w/ lush tropical trees & palms creating a serene home oasis for relaxing pool days, BBQ’s & dips in the jetted spa! When feeling adventurous you will enjoy being close to all of the shops, restaurants, bars & attractions Downtown Delray has to offer. Beach (10min walk)/PineappleGrove(15 min walk)/AtlanticAve(20min walk)/IntercoastalDrawbridge(5min walk)

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.

Waterfront Retreat w Pool | Fully Remodeled 4BR

Fully renovated waterfront home, thoughtfully designed for comfort & functionality. The property offers 4 bedrooms & 3 bathrooms, including a cabana bath, & with blackout blinds. Highlights include a king primary suite, comfortable beds in every room, a screened-in pool, dock, & outdoor swing. Additional amenities include infant accessories, Tesla charger, & dedicated workspace. Situated in a quiet, family-friendly neighborhood & managed by experienced Superhosts for a 5-Star experience.

Modern 3BR Oasis with Private Pool | 7m to Beach

Escape to your 3-bedroom private pool oasis in the heart of Boynton Beach, where modern comfort meets charm. Surprises belong at birthdays—this Guest Favorite looks exactly like the photos, ensuring a gold star standard stay! Enjoy the sparkling in-ground pool, private patio with dining, and yard games like cornhole. With a full kitchen, laundry, and quick I-95 access to beaches, boats, and dining, it’s the perfect blend of relaxation and convenience for a wonderful South Florida stay.

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!

15 Managed by Brampton Park

This beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and South Florida lifestyle. Located just 1.5 miles from the beach and only 1.5 miles from Atlantic Avenue, you’ll enjoy the best of Delray Beach right at your fingertips. Inside, the home features a spacious and inviting layout with a king en-suite primary bedroom and two guest bedrooms. Photos show a queen beds but they have been replaced with king beds.

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.

Private Heated Pool Getaway Near Downtown Delray

Welcome to your perfect getaway in a beautiful first-floor duplex, nestled in a quiet, family-friendly neighborhood just minutes from vibrant downtown Delray Beach. You’re less than a 10-minute drive to the beach and all the amazing restaurants, shops, and nightlife Delray has to offer. Relax in your private pool and backyard oasis, complete with a BBQ grill – perfect for enjoying sunny Florida days and warm tropical evenings.

Honey Hole & Bear Den| Heated Pool | Delray Beach

Welcome to the Honey Hole! This family-friendly beach getaway is sure to have any guest relaxing all year round. Situated in a quiet and private neighborhood this home is perfect for all your vacation needs. This completely renovated home is a 5 minute drive down Atlantic Avenue to downtown and the beaches. You can find restaurants, shops, parks, boat tours, and much more locally. We look forward to hosting you!