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Florida Vacation Rentals with Pools

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10.0 (192 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Why Choose Rent By Owner for your Florida 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 Florida

When should you plan your Vacation Rentals with Pools stay?

Choosing the ideal time to visit this destination ensures you can enjoy your stay in the region’s rentals with pools at their best, whether you prefer the bustling summer months or the quieter off-season when the area offers a more relaxed atmosphere.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, this destination attracts visitors seeking warm weather and sunshine, making it an ideal time for booking rentals with pools to enjoy outdoor relaxation.

Average Temperature Daytime: 75°F to 78°F - Nighttime: 55°F to 60°F
spring
Spring Break (March to April)

This popular travel period sees many travelers visiting the area for springtime festivities, so booking a rental with a pool ensures you can unwind comfortably after day trips or sightseeing.

Average Temperature Daytime: 80°F to 85°F - Nighttime: 60°F to 65°F

Off-Season Highlights

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Late Summer (August to September)

As summer winds down, fewer visitors are in the region, providing you with more privacy and better deals on rentals with pools while still enjoying warm temperatures.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 70°F to 75°F
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Fall (October to November)

With less hustle and bustle, this is a great time to relax at your preferred rental with a pool, experiencing comfortable weather before the peak winter season begins.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 55°F to 65°F

Weekly Weather Forecast for Florida

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 a private outdoor pool to relax and unwind during your stay in Florida.
  • Take advantage of spacious patios or decks perfect for outdoor dining and entertaining.
  • Benefit from lush landscaped gardens that offer privacy and scenic views in this popular area.
  • Make use of outdoor grills and barbecue stations to prepare meals al fresco with ease.
  • Relax on loungers and sun chairs by the poolside, ideal for soaking up the Florida sunshine.
  • Utilize shaded sitting areas or pergolas for comfortable outdoor gatherings regardless of the weather.
  • Access outdoor recreational spaces such as tennis courts or playgrounds if available in the property community.
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Family Activities

  • Visit Walt Disney World Resort: Experience the magic with your family at this iconic theme park, offering countless attractions and entertainment options suited for all ages.
  • Explore SeaWorld Orlando: Discover marine life shows and interactive exhibits that captivate children and adults alike in this popular aquatic theme park.
  • Enjoy Florida's beaches: Relax, swim, and build sandcastles on the pristine shores of nearby beaches, perfect for family fun in the sun.
  • Discover Legoland Florida: Engage in creative rides and interactive LEGO attractions designed to inspire and entertain young builders and their families.
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Adult Activities

  • Relax at local beaches: Spend your days lounging on pristine sands and soaking up the sun in this region’s famous coastal areas, perfect for unwinding after a day of exploring.
  • Experience vibrant nightlife: Discover lively bars and entertainment venues that offer a dynamic atmosphere to enjoy evenings with friends or a romantic night out.
  • Visit world-class theme parks: Enjoy thrilling rides and family-friendly attractions in nearby amusement parks, making it an exciting addition to your stay here.
  • Explore nature reserves and parks: Take guided tours or hikes through lush landscapes and protected areas to connect with the natural beauty of the region.

Other Places to Stay in Florida, FL

Florida Gulf Coast
North West Florida
Fort Walton Beach - Destin
Osceola County
Panama City Beach
Disney's Maingate West

Florida Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy your rental with pools and the area's attractions with fewer crowds, enhancing your overall experience.
  • Explore Local Recreation Activities: Take advantage of the region's outdoor offerings by engaging in water sports or nature excursions, making your stay both active and memorable.
  • Choose a Central Location: Booking a property close to popular spots ensures easy access to beaches, dining, and entertainment, maximizing your leisure time here.
  • Book Early for Best Availability: Reserving your rentals especially with pools in advance guarantees better selection and securement of your preferred dates for a seamless vacation.

Transportation Options

  • Rental Cars Renting a car provides you with the flexibility to explore the region at your own pace, especially when choosing rentals with pools that are conveniently located near popular attractions.
  • Public Transit Buses and trains offer an affordable way to navigate this area, making it easy to access various neighborhoods and relax by your rental’s pool after a day of sightseeing.
  • Ride-Sharing Services Companies like Uber and Lyft offer convenient transportation options, allowing you to travel comfortably between your accommodations and local points of interest without hassle.
  • Taxi Services Taxis remain a reliable choice for quick trips around here, ensuring you can easily reach your destination and unwind in your rental with a refreshing pool.

Local Customs Options

  • Southern Hospitality: Expect warm and welcoming interactions with locals who take pride in their friendly demeanor and courteous approach.
  • Outdoor Dining Etiquette: In many areas, it's customary to enjoy meals al fresco, especially during warm weather, emphasizing casual yet respectful outdoor socializing.
  • Beach Customs: Respect for beach rules, such as designated swimming areas and environmental conservation efforts, ensures a pleasant experience for all visitors.
  • Festive Celebrations: Participating in regional festivals often involves embracing vibrant traditions, music, and dress, contributing to a lively local culture.

Frequently Asked Questions About Florida Rentals with Pools

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

Currently, the total number of properties listed by RBO in 2026 is over 279824 in the Florida area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Florida. 

3. What is the cancellation policy for a rental with a pool in this destination?

Cancellation policies vary depending on the property listing. You should review the specific cancellation terms for each rental before booking, which are detailed on the listing page or can be confirmed by contacting the property owner.

4. Are there any additional fees for using the pool during my stay?

Additional fees related to pool usage, if applicable, will be specified in the rental listing. Be sure to read the property details carefully or reach out directly to the owner for clarification on any extra charges.

5. How do I confirm the availability of a rental with a private pool in the area?

Availability can be checked directly on the listing page when selecting your dates. For real-time confirmation or to discuss specific requirements, contact the property owner or host through the booking platform.

6. What amenities are typically included with rentals that feature pools here?

Most rentals with pools offer amenities such as outdoor furniture, loungers, and sometimes additional features like hot tubs or pool heating. Details about these amenities are provided on each listing, so reviewing the description ensures you know what to expect.

7. What should I know about the check-in and check-out process for pool rentals here?

Check-in and check-out procedures are outlined in each property listing. To ensure a smooth experience, you can contact the owner beforehand for specific instructions or any questions regarding access to the pool and the property.

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