Holiday rentals with a pool in Delray Beach

231 | Sleeps 8 | Pool | Tiki | by DelrayNightly

DELRAY NIGHTLY VACATION RENTALS - 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 Sout

•Floasis• Your private FL Oasis 5 min to beach!

Kick back, relax and recharge in this calm stylish space! Floasis is located 1.3 miles from the beach, with lots of activities, restaurants and shops nearby... but honestly, once you arrive, you won't want to leave the house! You will have your private good size pool, hot tub, an amazing covered deck to relax and dine and a big grassy area for the kids or dogs to run, yoga, relaxation or just for soaking in the florida weather! It's the perfect oasis for a couple, a small family, or 2 couples!

Luxe Private Pool & Spa*2 King Bds*Heart of Delray

🌴 Serenity Palms Villa 🌴 Escape to your own private retreat in the heart of Delray Beach. Enjoy a private saltwater pool, spa, and outdoor spaces designed for effortless 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.”

Private Pool Oasis | Steps to Atlantic Ave

Private pool retreat in Delray Beach- just 45 minutes from Hard Rock Stadium. Skip the Miami crowds and stay in your own private tropical retreat during the 2026 World Cup. The Happy Mango Hideaway is a fully private 2-bedroom, pet-friendly cottage with a heated saltwater pool, spa-style bathroom (renovated Oct 2025), full kitchen, fast Wi-Fi, and workspace. Walk to Atlantic Ave’s restaurants, cafés, and nightlife- then come home to your backyard oasis and unwind in peace after match day.

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.

Luxurious waterfront mansion - large heated pool

This Luxurious water front mansion is directly across the intercoastal offering over 240' of dockage, large yacht are welcome Enjoy an incredible Pool and all the comfort and delicate taste. This family-friendly hidden gem offers sun, fun and adventure with watersports, fishing, shopping, dining and much more! Located in the heart of Florida’s Gold Coast, offering some of the warmest and clearest waters, welcoming sandy beaches and calming breezes. An unforgettable vacation awaits you!

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.

5 Min to Beach - Heated Pool - Bikes Included

Nestled in historic Delray, this elegant and completely updated home offers 3BD, 3.5BA + office spanning over 2,100 sp ft. The kitchen features quartz countertops + all new appliances. Laundry downstairs and upstairs. Patio w. private salt water pool and seating area with screens. Double garage with 4 bicycles + hanger for your use. Located just a few steps from vibrant Downtown Delray with lots of bars, restaurants, live music, festivals, farmer’s market and just minutes from the beach.

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!

The Dream Delray/ 4 BR En-suite Pool Home

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.

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.

Waterfront, Spa, Htd Pool, Billiards, Lanai, Canal

Bachelorette weekends, birthday trips, family vacations — this is the house groups keep coming back to. Heated pool and spa on a private canal, screened lanai with string lights, billiards, and a dock where guests watch the sun go down. Sleeps 10. Hosts respond in minutes and know every great restaurant and hidden gem in Delray. 5 minutes to Atlantic Ave. Kayaks, paddleboards, and fishing gear included. 5 minutes to the beach.