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  2. Florida
  3. Pensacola
  4. Milton
  5. Vacation Rentals with Pools

Milton Vacation Rentals with Pools

7.0 (252 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
8.8 (17 Reviews)
Other
  • Air Conditioner
  • Parking
  • Pet Friendly

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

What makes our Vacation Rentals with Pools special?

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

Best Times to Visit Milton

When should you plan your Vacation Rentals with Pools stay?

Choosing the optimal time to visit here allows you to enjoy ideal weather and better availability of rentals with pools in this destination, ensuring your vacation experience in Milton, Florida, USA, is both relaxing and memorable.

Peak Season Highlights

spring
Spring (March to May)

During spring, you can enjoy mild weather and blooming landscapes, making it an ideal time to relax in your rentals with pools here. The region experiences pleasant daytime temperatures, perfect for outdoor activities.

Average Temperature Daytime: 70°F - 80°F - Nighttime: 50°F - 60°F
summer
Summer (June to August)

The summer months bring warm, sunny days, encouraging outdoor lounging and swimming in your rentals with pools. This is the most popular season for visitors seeking a vibrant atmosphere and long daylight hours.

Average Temperature Daytime: 85°F - 90°F - Nighttime: 65°F - 75°F

Off-Season Highlights

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Fall (September to November)

In fall, the area cools down slightly, offering a more relaxed experience with fewer crowds at your rentals with pools. The moderate temperatures are comfortable for enjoying the outdoors without the peak season hustle.

Average Temperature Daytime: 75°F - 85°F - Nighttime: 55°F - 65°F
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Winter (December to February)

Winter presents cooler weather, making it a quieter time to visit. While outdoor swimming might be less appealing, the peaceful environment makes it suitable for those seeking a tranquil retreat in rentals with pools.

Average Temperature Daytime: 55°F - 65°F - Nighttime: 40°F - 50°F

Weekly Weather Forecast for Milton

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 relaxing by a private or shared swimming pool, perfect for unwinding after exploring the region’s natural beauty.
  • Make use of outdoor seating areas such as patios or decks, ideal for al fresco dining or morning coffee.
  • Take advantage of barbecue grills for outdoor cooking sessions, great for gatherings with family or friends.
  • Benefit from well-maintained walking or biking paths that allow you to explore the scenic surroundings comfortably.
  • Relax in landscaped gardens or yards that offer a peaceful outdoor retreat during your stay.
  • Access nearby outdoor recreational amenities like playgrounds or sports courts, suitable for active guests.
  • Utilize shaded pergolas or gazebos, providing comfortable shelter for outdoor socializing in the warm Florida sun.
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Family Activities

  • Milton Community Center Park Enjoy family-friendly outdoor activities and open green spaces perfect for picnics and casual sports.
  • Blackwater Heritage State Trail Explore this scenic trail on family bike rides or nature walks that showcase the natural beauty of the region.
  • Imagination Station Playground Stimulate your children's creativity at this vibrant playground designed for safe and engaging play experiences.
  • Milton Historical Park Discover local history through interactive exhibits and guided tours suitable for all ages in this charming town setting.
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Adult Activities

  • Milton Nature Trails Discover serene walking and biking paths where you can enjoy the natural beauty of the region while staying active.
  • Blackwater River State Forest Experience outdoor adventures such as kayaking, canoeing, or simply relaxing in scenic surroundings close to your rental with a pool.
  • Historic Downtown Milton Explore charming shops, local eateries, and cultural landmarks that highlight the area's rich history and community spirit.
  • Blue Wahoos Stadium Catch a lively minor league baseball game and enjoy entertainment options that make for a fun outing during your stay.

Other Places to Stay in Milton, FL

Santa Rosa County
Blackwater River State Forest
Secret Beach
Adventures Unlimited Outdoor Center
Naval Air Station Whiting Field
Clear Creek
Arcadia Mill Archaelogical Site
Santa Rosa Health Care
Blackwater Heritage State Trail

Milton Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Peak Seasons: Book your rentals with pools well in advance to secure the best options during busy times in the area.
  • Explore Local Amenities: Take advantage of nearby parks and outdoor spaces that enhance your stay in this region, making your visit more enjoyable and active.
  • Check Property Details: Review property listings thoroughly to ensure your chosen rental offers the amenities you desire, especially a private pool for ultimate relaxation.
  • Maximize Your Pool Time: Schedule pool activities early in the day or late afternoon to avoid crowds and make the most of your tranquil experiences here.

Transportation Options

  • Milton Transit: A reliable public transportation system offering convenient bus routes to explore the area, making it easy to access local attractions and accommodations.
  • Rental Cars: Multiple rental car agencies are available in the region, providing the flexibility to travel at your own pace around Milton and nearby destinations.
  • Taxis and Ride-Sharing Services: Modern ride-sharing options like Uber and Lyft operate throughout the area, offering a quick and comfortable way to reach your rental with pools without hassle.
  • Bike Rentals: For those seeking an eco-friendly and active way to see the surroundings, bike rentals provide a scenic and flexible transportation alternative here.

Local Customs Options

  • Southern Hospitality: Expect warm welcomes and friendly gestures that reflect the region's renowned hospitality, making your stay more enjoyable.
  • Local Seafood Cuisine: Enjoy a tradition of fresh seafood dishes often shared during community gatherings, giving you a taste of regional flavors.
  • Community Events and Festivals: Experience local celebrations that showcase Milton's heritage, providing a glimpse into the area’s cultural traditions.
  • Respect for Nature: Observe a strong appreciation for natural surroundings, with customs emphasizing conservation and outdoor enjoyment in this scenic destination.

Frequently Asked Questions About Milton Rentals with Pools

1. What are the top Rentals With Pools in Milton?

There are a lot of options in Milton. If you plan on staying in the Milton area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Rentals With Pools in Milton:

2. How many Rentals With Pools are available in Milton?

Currently, the total number of properties listed by RBO in 2026 is over 26 in the Milton area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Milton. 

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

Cancellation policies vary by listing. You should review the specific terms on the property’s page or contact the owner directly to understand the conditions and any applicable fees.

4. Are there any additional fees I should be aware of when booking a rental with a pool?

Additional fees such as cleaning, security deposits, or pool usage charges may apply. Please check the listing details or reach out to the owner for a complete fee breakdown before booking.

5. How do I confirm the availability of a rental with a pool in Milton, Florida?

Availability is updated regularly on the listing page. You can verify real-time status and request bookings directly through the platform or contact the owner for confirmation.

6. What amenities are typically included with rentals that have pools in the region?

Most rentals offer amenities like fully equipped kitchens, Wi-Fi, outdoor lounging areas, and sometimes additional features such as hot tubs or BBQ grills. Details are listed on each property’s page, so reviewing individual listings is recommended.

7. Is it possible to get assistance if I encounter issues during my stay at a rental with a pool?

Yes, customer support is available to help resolve any concerns. Contact the property owner or the support team promptly via the platform for assistance during your stay.

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