Sumter County Vacation Rentals with Pools
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $149/Night
For 7 Nights US $1,043
1388.54 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Villa
- Fireplace/Heating
- Pool
- View
US $165/Night
For 7 Nights US $1,155
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Pool
- Ocean View
US $375/Night
For 7 Nights US $2,624
1500 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $110/Night
For 7 Nights US $767
1474.66 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Pool
US $290/Night
For 7 Nights US $2,030
1600 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $159/Night
For 7 Nights US $1,110
1097.92 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Pool
- Parking
- Internet
US $146/Night
For 7 Nights US $1,022
1248 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $201/Night
For 7 Nights US $1,410
1194.79 ft²
4 Guests
1 Bedroom
2 Bathrooms
House
- Oceanfront
- Spa
- Fireplace/Heating
US $157/Night
For 7 Nights US $1,099
1250 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
US $164/Night
For 7 Nights US $1,149
1732.99 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Oceanfront
- Spa
- Fireplace/Heating
US $231/Night
For 7 Nights US $1,618
1478 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $246/Night
For 7 Nights US $1,722
Why Choose Rent By Owner for your Sumter County Vacation Rentals with Pools?
What makes our Vacation Rentals with Pools special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Sumter County
When should you plan your Vacation Rentals with Pools stay?
Timing your vacation here can enhance your experience, as the best months to book rentals with pools in Sumter County are during the warmer seasons when you can fully enjoy the region's inviting pools and pleasant weather.
Peak Season Highlights
Winter (December to February)
During the winter months, you'll find this destination bustling with visitors seeking mild weather and enjoyable outdoor activities. Booking your rentals with pools now ensures a relaxing escape with plenty of sunshine.
Average Temperature Daytime: 70°F - Nighttime: 50°F
Spring (March to May)
Spring is a popular time to visit, with warm days and vibrant landscapes. Securing your rentals with pools during this season guarantees comfortable stays while exploring the area's natural beauty.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Off-Season Highlights
Summer (June to August)
This period sees fewer visitors, making it an ideal time to enjoy your stay with less crowds. Your rentals with pools are perfect for cooling off after daytime adventures in the region.
Average Temperature Daytime: 90°F - Nighttime: 70°F
Fall (September to November)
Fall offers cooler temperatures and quieter surroundings, providing a peaceful atmosphere for your getaway. Booking properties with pools now lets you unwind in comfort as the weather gradually cools.
Average Temperature Daytime: 80°F - Nighttime: 60°F
Weekly Weather Forecast for Sumter County
How to Book Your Sumter County Vacation Rentals with Pools
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals with pools. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
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.
Explore and book the perfect rental in Sumter County
Common Vacation Rentals with Pools Amenities
What amenities can you expect?
Our Vacation Rentals with Pools are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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 your stay with a private or shared swimming pool, perfect for relaxing and unwinding after exploring the area.
- Take advantage of outdoor dining areas or patios where you can savor meals al fresco in the warm Florida sunshine.
- Make the most of spacious yards or gardens that are ideal for outdoor activities or leisurely walks around your rental.
- Experience the convenience of outdoor grills or barbeque stations to create delicious meals during your visit.
- Stay active with access to tennis courts, basketball hoops, or other sports facilities often available in vacation communities here.
- Find tranquility with shaded lounging areas or hammocks set up within outdoor communal spaces or gardens.
- Discover nearby outdoor recreation options like walking trails, parks, or lakes, enhancing your outdoor experience in the region.
Top Attractions Around Sumter County
What attractions are nearby?
Within this destination, you can enjoy a variety of outdoor activities and attractions just moments from your rentals with pools, making it easy to explore the natural beauty and local culture that define the region.
Family Activities
- The Sumter County Recreational Park Enjoy outdoor family fun at this popular park featuring playgrounds, picnic areas, and open spaces for all ages.
- The Florida Mural Trail Explore colorful public murals that provide a vibrant cultural experience perfect for family outings and photo opportunities.
- Local Nature Trails and Parks Discover scenic walking trails and nature preserves where your family can reconnect with the outdoors and observe native wildlife.
- Community Events and Festivals Participate in seasonal festivals and family-friendly events hosted throughout the destination, offering entertainment and local flavors.
Adult Activities
- Golfing at The Villages: Enjoy a relaxing day on world-class golf courses that are renowned within the region, perfect for adult enthusiasts seeking leisure and sport.
- Wine Tasting Tours: Indulge in local wine tasting experiences offered by nearby wineries that highlight the area's vibrant viniculture scene.
- Historic District Exploration: Discover the charm of local historic districts with walking tours and cultural landmarks that provide insight into the area's rich history.
- Nature and Wildlife Viewing: Embark on scenic outdoor excursions in nature preserves or parks that showcase the diverse flora and fauna native to the region.
Other Places to Stay in Sumter County, FL
Virginia Trace
Liberty Park
Mallory Square
Santiago
Pennecamp
The Villages
Wildwood
Bushnell
Lake Deaton
Lynnhaven
Santo Domingo
Sumter County Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the area's parks and scenic spots to enjoy the natural beauty surrounding your rentals with pools.
- Visit nearby attractions: Seek out popular sites and events in the region to enrich your stay and get a true taste of this destination.
- Plan your days efficiently: Use local maps and guides to make the most of your time, ensuring you visit key spots while relaxing by your rentals with pools.
- Choose accommodations with amenities: Select rentals with pools that offer added comfort and convenience for both relaxation and socializing during your visit.
Transportation Options
- Sumter County Regional Airport This local airport offers convenient flights and ground transportation options, making it easy to access your rental with pools in the area.
- Greyhound Bus Station Providing intercity bus services, this station is a reliable choice for travelers exploring the region without a car.
- Rental Car Services Major providers operate here, giving you the flexibility to explore the entire destination at your own pace.
- Taxi and Rideshare Services Available throughout the region, these options provide quick and comfortable transport directly to your vacation rental with pools.
Local Customs Options
- Gambling Customs: Visitors often partake in the region's historic gaming traditions, which are a popular way to enjoy local entertainment and hospitality.
- Golf Etiquette: The area’s numerous golf courses hold cherished customs centered around sportsmanship and respect for fellow players.
- Community Festivals: Local festivals celebrate Florida’s rich history and culture, offering authentic experiences for visitors seeking immersion in regional traditions.
- Religious Practices: The community observes distinctive religious customs that reflect its diverse heritage and deeply rooted spiritual values.
Sumter County Vacation Rentals with Pools Frequently Asked Questions
1. What are the top Rentals With Pools in Sumter County?
There are a lot of options in Sumter County. If you plan on staying in the Sumter County 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 Sumter County:
- May 16–23 PreMemorial Day Getaway: Golf-Front Home, Solar Pool, Free Cart & WiFi
- Our Village Gem-Dog Friendly-Cozy & Peaceful-Walk to Sumter Square
- Nicest Location & Fully Equipped Charming Home in the “Heart” of The Villages.
- Walk to Lake Sumter Landing! Our Village Gem - 10 Star - w/Golf Cart
- Beautiful 2 BR wGas Golf Cart in Duval. All 10 star reviews!
- Hot Tub House Escape – 3BR in The Villages at Special Rates
- Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI
- Fully Furnished Brand New Villa in Village of St. Catherine's with Cart
- Charming 3/2 Virginia Trace Villa, next to Lake Sumter Landing, with golf cart
- Modern Comfort & Prime Location in The Villages – Golf Cart Included!
2. How many Rentals With Pools are available in Sumter County?
Currently, the total number of properties listed by RBO in 2026 is over 1476 in the Sumter County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Sumter County.
3. What is the cancellation policy for rentals with pools in this area?
The cancellation policies vary by property, so it’s important to review the specific listing details or contact the owner directly to understand the terms before booking your stay.
4. How do I find rentals with pools that are available during my travel dates?
You can filter your search on the booking website to include only rentals with pools and check availability for your desired dates, ensuring a seamless planning experience.
5. Are there any additional fees associated with booking a rental with a pool in this destination?
Additional fees may apply depending on the property, such as cleaning or pool maintenance fees. It’s advisable to review the listing details or reach out to the owner for clarification.
6. What amenities are typically included with rentals featuring pools here?
Most rentals with pools offer amenities like outdoor furniture, barbecue grills, and sometimes additional features like hot tubs. Confirm the specific amenities with the property owner before booking.
7. How do I ensure safety when staying at a rental with a pool in this region?
Safety measures vary by property, so it’s best to read the safety guidelines provided in the listing or contact the owner directly to inquire about pool safety features and rules.
More Rentals You May Like Near Sumter County
1679.17 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Oceanfront
- Fireplace/Heating
- Pool
US $188/Night
For 7 Nights US $1,317
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $90/Night
For 7 Nights US $629
1040 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Pet Friendly
US $191/Night
For 7 Nights US $1,336
1300 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $95/Night
For 7 Nights US $667
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $147/Night
For 7 Nights US $1,027
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $121/Night
For 7 Nights US $847
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $120/Night
For 7 Nights US $839
1056 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
US $222/Night
For 7 Nights US $1,554
1041 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $142/Night
For 7 Nights US $991
1279 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $127/Night
For 7 Nights US $891
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $116/Night
For 7 Nights US $812
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Spa
- Fireplace/Heating
- Pool
US $462/Night
For 7 Nights US $3,237
