Delray Beach Vacation Rentals with Pools

10.0
Exceptional
(1 Review)
4 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
US $514/Night For 7 Nights US $3,597
10.0
Exceptional
(8 Reviews)
118.4 ft² 6 Guests 3 Bedrooms 3 Bathrooms
Ocean View House
  • Oceanfront
  • Pool
  • Ocean View
US $579/Night For 7 Nights US $4,053
9.4
Exceptional
(290 Reviews)
1 Bedroom 1 Bathroom
Ocean View Condo
  • Fireplace/Heating
  • Pool
  • Ocean View
US $257/Night For 7 Nights US $1,799
New
1110 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
US $521/Night For 7 Nights US $3,650
10.0
Exceptional
(3 Reviews)
1625.35 ft² 8 Guests 3 Bedrooms 2 Bathrooms
Free Cancellation House
  • Oceanfront
  • Pool
  • Ocean View
US $678/Night For 7 Nights US $4,743
New
6 Guests 3 Bedrooms 2 Bathrooms
Family Friendly House
  • Private Pool
  • Pool
  • Balcony/Terrace
US $449/Night For 7 Nights US $3,142
10.0
Exceptional
(3 Reviews)
182.99 ft² 9 Guests 3 Bedrooms 3 Bathrooms
House
  • Oceanfront
  • Pool
  • Ocean View
US $452/Night For 7 Nights US $3,161
New
5 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
US $357/Night For 7 Nights US $2,497
10.0
Exceptional
(2 Reviews)
1399.31 ft² 8 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
US $640/Night For 7 Nights US $4,482
10.0
Exceptional
(39 Reviews)
851 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Condo
  • Oceanfront
  • Fireplace/Heating
  • Pool
US $300/Night For 7 Nights US $2,098
10.0
Exceptional
(2 Reviews)
1194.79 ft² 6 Guests 3 Bedrooms 1 Bathroom
Apartment
  • Oceanfront
  • Hot Tub
  • Fireplace/Heating
US $198/Night For 7 Nights US $1,386
10.0
Exceptional
(34 Reviews)
249 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Hot Tub
  • Fireplace/Heating
US $189/Night For 7 Nights US $1,323

Why Choose Rent By Owner for your Delray Beach Vacation Rentals with Pools?

What makes our Vacation Rentals with Pools special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Delray Beach

When should you plan your Vacation Rentals with Pools stay?

Choosing the optimal time to vacation here can help you enjoy pleasant weather and fewer crowds, making your stay in this destination's rentals with pools even more relaxing and memorable.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you can enjoy the warm and sunny weather typical of this destination, making it an ideal time for relaxing by your rentals with pools in the area.

Average Temperature Daytime: 75-80°F - Nighttime: 60-65°F
spring
Spring Break (March to April)

This busy period attracts visitors seeking to escape colder climates, offering excellent opportunities to enjoy the region's vibrant atmosphere and your chosen rentals with pools.

Average Temperature Daytime: 78-83°F - Nighttime: 62-68°F

Off-Season Highlights

image
Summer (June to August)

While summer brings higher temperatures and occasional rain showers, it also offers quieter surroundings and more availability for rentals with pools.

Average Temperature Daytime: 85-90°F - Nighttime: 75-77°F
image
Fall (September to November)

You’ll find fewer crowds during the fall, making it a peaceful time to enjoy your stay and unwind by the pool in this coastal destination.

Average Temperature Daytime: 80-85°F - Nighttime: 65-70°F

Weekly Weather Forecast for Delray Beach

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy private or shared outdoor swimming pools to relax under the sun.
  • Take advantage of lush landscaped gardens and spacious patios for outdoor dining and lounging.
  • Make use of outdoor grilling areas to host memorable barbecues in this coastal region.
  • Stay active with tennis courts, pickleball, or other sports facilities available in some rentals.
  • Relax in shaded cabanas or poolside loungers designed for ultimate comfort.
  • Experience outdoor shower stations perfect for rinsing off after a day at the nearby beaches.
  • Benefit from fenced yards or secure outdoor spaces ideal for families and pets in this destination.
image
image

Family Activities

  • Atlantic Avenue Shopping and Dining: Explore the vibrant area filled with family-friendly restaurants, shops, and entertainment options that capture the lively spirit of the region.
  • Delray Beach Children's Garden: Enjoy a day outdoors at this interactive garden designed for kids to learn about nature and engage in hands-on activities.
  • SilverBall Pinball Museum: Experience hours of fun with vintage pinball machines and arcade games suitable for all ages in this nostalgic entertainment spot.
  • Pineapple Grove Arts District: Discover local art galleries, colorful murals, and cultural exhibits that inspire creativity and family engagement throughout this artistic neighborhood.
image

Adult Activities

  • Beachfront Relaxation Spend your days lounging on the pristine sands and soaking up the sun along the beautiful shoreline, just moments from your rental here.
  • Gourmet Dining Experiences Explore the vibrant culinary scene with a variety of upscale restaurants offering fresh seafood and local flavors in the area.
  • Arts and Cultural Events Immerse yourself in the local art galleries, live music performances, and cultural festivals that highlight the region's creative spirit.
  • Nightlife and Entertainment Enjoy lively bars, chic lounges, and entertainment venues that provide vibrant nightlife options for adults seeking evening fun.

Other Places to Stay in Delray Beach, FL

Pineapple Grove Arts District
Highland Park Delray
Del-Ida Park Historic District
Lake Ida Shores

Delray Beach Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local beaches: Make the most of your stay by visiting nearby beaches where you can enjoy the sun, sand, and calm waters just a short drive from your rental with a pool.
  • Visit vibrant local dining: Sample the region’s diverse culinary scene at highly recommended restaurants to experience authentic flavors that complement your relaxing getaway.
  • Discover outdoor activities: Take advantage of scenic parks and water-based adventures available in the area to add variety to your vacation experience.
  • Plan for sunset evenings: Unwind by your rental’s private pool or head to popular waterfront spots to enjoy breathtaking sunsets unique to this destination’s coastline.

Transportation Options

  • Taxi Services: Reliable taxi companies operate throughout the area, offering convenient transportation options to explore different neighborhoods and attractions.
  • Public Transportation (Tri-Rail and Buses): The local transit system provides affordable and accessible options for traveling around here without the need for a car.
  • Rental Cars: Numerous rental agencies are available, allowing you to drive comfortably and independently to visit nearby beaches, shops, and dining spots.
  • Rideshare Services: Popular rideshare platforms like Uber and Lyft offer modern and efficient transportation choices in this destination for flexible travel plans.

Local Customs Options

  • Shoreline Preservation: Locals in the area take pride in preserving the pristine beaches and natural shoreline, making visits here especially scenic and relaxing.
  • Art Deco Influence: The region showcases a unique blend of historic and modern architecture, reflecting local appreciation for vibrant art styles alongside contemporary design.
  • Seafood Cuisine: Enjoying fresh seafood is a cherished custom, with many dining spots emphasizing locally caught fish and regional flavors.
  • Community Festivals: Participating in lively street festivals and events is a common way residents celebrate their local culture while welcoming visitors to the area’s vibrant atmosphere.

Delray Beach Vacation Rentals with Pools Frequently Asked Questions

2. How many Rentals With Pools are available in Delray Beach?

Currently, the total number of properties listed by RBO in 2026 is over 663 in the Delray Beach area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Delray Beach. 

3. What is the cancellation policy for rentals with pools in this destination?

Cancellation policies vary by property. You should review the specific listing details or contact the property owner directly to understand their terms before booking.

4. Are there any additional fees associated with staying in a rental with a pool?

Additional fees, such as cleaning or service charges, are specified in each listing. To get accurate information, please refer to the individual property details or reach out to the host.

5. How do I ensure the rental with a pool meets safety standards?

Safety features and regulations are typically outlined in the property description. For further assurance, contact the property owner to inquire about safety measures implemented at the rental.

6. Can I stay during peak seasons or holidays in these rentals?

Availability during peak seasons or holidays depends on the property's booking schedule. It’s advisable to book early and confirm availability with the host through the listing specifics.

7. What amenities are included with the pool in these rentals?

Amenities can range from pool heating to loungers and umbrellas. For detailed information on what’s provided, review the property listing or contact the owner directly.

More Rentals You May Like Near Delray Beach

10.0
Exceptional
(2 Reviews)
559.72 ft² 6 Guests 1 Bedroom 1 Bathroom
Apartment
  • Oceanfront
  • Fireplace/Heating
  • Pool
US $350/Night For 7 Nights US $2,450
10.0
Exceptional
(31 Reviews)
1700 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Fireplace/Heating
  • Pool
US $340/Night For 7 Nights US $2,380
10.0
Exceptional
(27 Reviews)
1000 ft² 4 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Hot Tub
US $665/Night For 7 Nights US $4,656
10.0
Exceptional
(22 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Ocean View Villa
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
US $173/Night For 7 Nights US $1,208
10.0
Exceptional
(21 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Fireplace/Heating
  • Pool
US $297/Night For 7 Nights US $2,077
10.0
Exceptional
(19 Reviews)
8 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
US $506/Night For 7 Nights US $3,539
10.0
Exceptional
(18 Reviews)
850 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Condo
  • Oceanfront
  • Fireplace/Heating
  • Pool
US $326/Night For 7 Nights US $2,281
10.0
Exceptional
(18 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Ocean View Apartment
  • Oceanfront
  • Hot Tub
  • Fireplace/Heating
US $158/Night For 7 Nights US $1,105
10.0
Exceptional
(14 Reviews)
324 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Cottage
  • Fireplace/Heating
  • Pool
  • Ocean View
US $296/Night For 7 Nights US $2,071
10.0
Exceptional
(13 Reviews)
750 ft² 4 Guests 2 Bedrooms 1 Bathroom
Ocean View Cottage
  • Private Pool
  • Oceanfront
  • Fireplace/Heating
US $540/Night For 7 Nights US $3,780
10.0
Exceptional
(13 Reviews)
4 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Private Pool
  • Hot Tub
  • Pool
US $278/Night For 7 Nights US $1,948
10.0
Exceptional
(11 Reviews)
5 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Apartment
  • Fireplace/Heating
  • Pool
  • Balcony/Terrace
US $273/Night For 7 Nights US $1,908