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Florida Vacation Rentals with Pools

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9.3 (22 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
9.3 (3 Reviews)
House
  • Air Conditioner
  • View
  • Security/Safety
5.2 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
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9.3 (55 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
7.3 (3 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Child Friendly

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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 vacation in this destination ensures you enjoy the best weather and availability when booking rentals with pools, allowing you to relax and make the most of your stay in the region.

Peak Season Highlights

spring
December to April

During these months, you'll experience the warmest and most pleasant weather, ideal for enjoying your rentals with pools in this region. It's the perfect time to relax and soak up the sun.

Average Temperature Daytime: 25°C to 30°C - Nighttime: 15°C to 20°C
spring
June to August

The summer months bring lively atmosphere and higher temperatures, making it a popular period for visitors seeking sunny days and poolside relaxation in the area.

Average Temperature Daytime: 27°C to 32°C - Nighttime: 17°C to 22°C

Off-Season Highlights

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May and November

During these shoulder months, you can often find fewer crowds and better deals on rentals with pools while still enjoying mild and comfortable weather in this destination.

Average Temperature Daytime: 20°C to 25°C - Nighttime: 12°C to 16°C
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September to October

Late spring to early summer sees a slight dip in tourist numbers, offering a more tranquil experience with pleasant temperatures for enjoying your stay here.

Average Temperature Daytime: 22°C to 27°C - Nighttime: 14°C to 19°C

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 swimming pool to cool off during warm days exploring the region.
  • Take advantage of spacious outdoor patios or decks perfect for relaxing or dining al fresco.
  • Benefit from lush, well-maintained gardens that create a serene outdoor ambiance.
  • Make use of outdoor showers for rinsing off after a day at nearby beaches or parks.
  • Spend time in shaded porches or verandas, ideal for unwinding while enjoying the surrounding scenery.
  • Utilize outdoor barbecue grills to host enjoyable cookouts with family or friends.
  • Explore the presence of outdoor lounging areas designed for soaking up the sun and taking in the area's natural beauty.
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Family Activities

  • Visit Punta del Este’s Beaches: Spend quality family time relaxing and playing on the famous beaches, where the gentle sands and warm waters create perfect conditions for children and adults alike.
  • Explore Isla Gorriti: Take a family-friendly boat trip to this nearby island, offering safe swimming spots and nature trails that showcase the region's natural beauty.
  • Enjoy a Day at The Casapueblo Museum: Discover the artistic charm of this unique building, which offers engaging exhibits and stunning sunset views that captivate visitors of all ages.
  • Experience Local Markets: Wander through bustling markets in the area, sampling local foods and browsing handcrafted souvenirs to immerse your family in regional culture.
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Adult Activities

  • Visit the local vineyards and wineries: Explore the region’s renowned vineyards and enjoy wine tasting tours that showcase the area's rich viticultural heritage.
  • Relax on pristine beaches: Spend your days lounging by the coastline, soaking up the sun, and swimming in the clear waters of this coastal destination.
  • Discover cultural attractions: Immerse yourself in the area’s vibrant arts scene through museums, galleries, and historic sites that tell the story of the region.
  • Engage in outdoor adventures: Take part in activities such as horseback riding, cycling, or nature walks to experience the scenic landscapes firsthand.

Other Places to Stay in Florida

Robaina Park
San Cono Chapel
Cerra Colorado
Jose Batlle y Ordonez
Venticinco de Agosto

Florida Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead Reserve your ideal rentals with pools in this region early to ensure availability and secure the best options for your stay.
  • Explore Local Culture Take time to experience the area's unique traditions and cuisine, enriching your visit beyond just relaxing by the pool.
  • Utilize Online Resources Use trusted platforms to find verified rentals with pools that match your preferences and budget effortlessly.
  • Embrace Outdoor Activities Make the most of the warm climate by participating in nearby outdoor pursuits, complementing your poolside relaxation.

Transportation Options

  • Personal Vehicles: Renting a car provides you with the flexibility to explore this destination at your own pace and visit various local attractions comfortably.
  • Public Buses: Local bus services are an affordable transportation option that connect key areas within the region, making it easy to navigate without a car.
  • Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber offer convenient, door-to-door transportation ideal for quick trips around the area.
  • Rental Bikes and Scooters: For short distances, bicycle and scooter rentals offer an eco-friendly way to enjoy the scenery and access nearby destinations easily.

Local Customs Options

  • Mateo Festival: Participating in this regional celebration offers a glimpse into local traditions and the vibrant community spirit here.
  • Gaucho Customs: Embracing the gaucho lifestyle, including traditional dress and horsemanship, is a common cultural expression in this region.
  • Uruguayan Barbecue (Asado): Enjoying an authentic asado is a cherished social activity that reflects the area's culinary heritage and communal values.
  • Tango Dance: The passionate dance of tango holds cultural significance, often showcased during festive occasions within the local community here.

Frequently Asked Questions About Florida Rentals with Pools

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

There are a lot of options in Florida. If you plan on staying in the Florida 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 Florida:

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

Currently, the total number of properties listed by RBO in 2026 is over 2 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 rentals with pools in this region?

Cancellation policies vary by property, so you will need to review the specific listing details or contact the property owner directly to understand the options available for your reservation.

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

Additional fees such as cleaning fees, security deposits, or service charges are typically outlined in the listing. It’s best to check the property’s detailed description or reach out to the owner for clarification.

5. Can I inquire about the availability of a rental with a pool during peak season?

Availability depends on the specific property and the time of year. To ensure your preferred dates are open, it’s recommended to review the calendar on the listing or contact the owner directly.

6. What amenities are included with the pool at these rentals?

Amenities can vary from property to property, but many include features like pool heating, loungers, or safety equipment. You should review the listing details or contact the owner to confirm the available amenities.

7. Is there a minimum stay requirement for rentals with pools in this area?

Minimum stay requirements are set by each property and can differ based on the season or owner preferences. For precise information, please check the listing details or contact the owner directly.