Discover Your Perfect Saint Leo Vacation Homes

Best Vacation Homes in Saint Leo

House
Map-icon
like-icon10.0
Exceptional
(41 Reviews)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R1,692/Night 7 Nights - R11,847
House
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
1 Bedroom 1 Bath 2 Guests 312.15 ft²
  • Parking
    Parking
  • Air Conditioner
    Air Conditioner
More amenities
R1,983/Night 7 Nights - R13,873
Hotel
Map-icon
like-icon8.8
Fabulous
(826 Reviews)
1 Bath
  • Pool
    Pool
  • Breakfast
    Breakfast
More amenities
R2,209/Night 7 Nights - R15,458
Cottage
Map-icon
like-icon10.0
Exceptional
(6 Reviews)
2 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R3,055/Night 7 Nights - R21,389
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House
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like-icon10.0
Exceptional
(3 Reviews)
3 Bedrooms 2 Baths 6 Guests 1216.32 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
More amenities
R3,584/Night 7 Nights - R25,082
House
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 1 Bath 4 Guests 947 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R3,057/Night 7 Nights - R21,406
House
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like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 1 Bath 5 Guests 800 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R2,743/Night 7 Nights - R19,200
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R9,928/Night 7 Nights - R69,495

Saint Leo Luxury Rentals

House
Map-icon
like-icon9.0
Exceptional
(6 Reviews)
5 Bedrooms 4 Baths 18 Guests 5574 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R34,528/Night 7 Nights - R241,706
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House
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1 Bedroom 4 Baths 18 Guests 5575.71 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R22,666/Night 7 Nights - R158,665
House
Map-icon
3 Bedrooms 2 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R18,168/Night 7 Nights - R127,177
House
Map-icon
like-icon10.0
Exceptional
(5 Reviews)
6 Bedrooms 4 Baths 12 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R16,960/Night 7 Nights - R118,713
New
House
Map-icon
7 Bedrooms 4 Baths 16 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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R15,098/Night 7 Nights - R105,689
House
Map-icon
3 Bedrooms 3 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R10,798/Night 7 Nights - R75,590
House
Map-icon
5 Bedrooms 3 Baths 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
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R8,986/Night 7 Nights - R62,910
New
Other
Map-icon
4 Bedrooms 2 Baths 16 Guests 4032 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R8,236/Night 7 Nights - R57,649

Saint Leo Pet Friendly Vacation Rentals

House
Map-icon
like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 6 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R3,294/Night 7 Nights - R23,056
star-icons-3
House
Map-icon
like-icon8.0
Excellent
(3 Reviews)
5 Bedrooms 3 Baths 10 Guests 2497.23 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R3,807/Night 7 Nights - R26,651
Cottage
Map-icon
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R2,882/Night 7 Nights - R20,180
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House
Map-icon
like-icon8.0
Excellent
(1 Review)
2 Bedrooms 1 Bath 4 Guests 850.35 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
R3,080/Night 7 Nights - R21,569
House
Map-icon
like-icon10.0
Exceptional
(51 Reviews)
3 Bedrooms 2 Baths 6 Guests 1400 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
R3,200/Night 7 Nights - R22,403
House
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
4 Bedrooms 2 Baths 8 Guests
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
R7,626/Night 7 Nights - R53,384
Villa
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 2 Baths 8 Guests 1500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R5,416/Night 7 Nights - R37,910
House
Map-icon
like-icon9.8
Exceptional
(31 Reviews)
3 Bedrooms 1 Bath 8 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R3,588/Night 7 Nights - R25,115

Saint Leo Large Vacation Homes

Villa
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
3 Bedrooms 2 Baths 6 Guests 1714 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
R6,892/Night 7 Nights - R48,253
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House
Map-icon
1 Bedroom 2 Baths 15 Guests 1108.68 ft²
  • Private Beach
    Private Beach
  • Skiing
    Skiing
More amenities
R2,967/Night 7 Nights - R20,769
Villa
Map-icon
like-icon10.0
Exceptional
(10 Reviews)
3 Bedrooms 2 Baths 6 Guests 1700 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R5,788/Night 7 Nights - R40,524
Villa
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3 Bedrooms 2 Baths 6 Guests 1700.7 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Parking
    Parking
More amenities
R5,940/Night 7 Nights - R41,586
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 2 Baths 10 Guests
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R4,433/Night 7 Nights - R31,030
House
Map-icon
like-icon8.4
Excellent
(7 Reviews)
5 Bedrooms 2 Baths 10 Guests 2500 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R6,590/Night 7 Nights - R46,129
House
Map-icon
like-icon8.0
Excellent
(2 Reviews)
5 Bedrooms 4 Baths 18 Guests
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R7,429/Night 7 Nights - R52,011
House
Map-icon
3 Bedrooms 2 Baths 10 Guests
  • Pet Friendly
    Pet Friendly
  • Air Conditioner
    Air Conditioner
More amenities
R5,856/Night 7 Nights - R40,998

Why Choose Rent By Owner for your Saint Leo Vacation Rental Homes?

What makes our Vacation Rentals 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 Saint Leo

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as this destination offers different charms and activities depending on the season and weather conditions in the area.

Peak Season Highlights

spring
Spring (March to May)

During spring, the area experiences warm weather that makes it ideal for exploring the outdoors and enjoying local activities. This season is popular among travelers seeking pleasant temperatures and vibrant natural scenery.

Average Temperature Daytime: 75°F - Nighttime: 55°F
autumn
Fall (September to November)

Autumn offers cooler temperatures and fewer crowds, creating a perfect setting for relaxed getaways and outdoor adventures. It’s an excellent time to enjoy the region's scenic beauty and comfortable climate.

Average Temperature Daytime: 78°F - Nighttime: 60°F

Off-Season Highlights

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Summer (June to August)

In summer, the region sees higher temperatures and increased humidity, making it ideal for those who enjoy hot weather and outdoor water activities. Booking during this time can offer more affordable options and less busy attractions.

Average Temperature Daytime: 88°F - Nighttime: 70°F
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Winter (December to February)

Winter months bring cooler weather with milder temperatures, providing a quieter atmosphere for visitors seeking tranquility. It’s a beneficial period for securing budget-friendly vacation rentals and avoiding peak crowds.

Average Temperature Daytime: 65°F - Nighttime: 45°F

Weekly Weather Forecast for Saint Leo

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 the area.
  • Take advantage of spacious outdoor patios or decks perfect for outdoor dining and gatherings.
  • Benefit from lush, well-maintained gardens that add to the scenic beauty of your rental property.
  • Make use of outdoor grilling facilities to enjoy delicious meals al fresco with family and friends.
  • Relax in a hammock or lounge chairs available on the outdoor space, ideal for soaking up the sunshine.
  • Explore nearby walking trails or nature paths accessible directly from your rental property.
  • Utilize outdoor recreational equipment like bicycles or kayaks provided for exploring the region’s natural landscapes.
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Family Activities

  • Saint Leo University Campus Tour: Explore the beautiful campus and enjoy family-friendly events that showcase the local educational spirit.
  • Linda Pederson Park: Spend a relaxing day outdoors at this scenic park, perfect for picnics, walking trails, and recreational activities for all ages.
  • Bullock Creek Preserve: Discover the natural beauty of the region with family-friendly hiking and wildlife viewing in this peaceful preserve.
  • Local Farmers Markets: Experience fresh regional produce and handmade crafts at markets that welcome families looking to enjoy the area's vibrant community scene.
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Adult Activities

  • Hiking at Lake Jovita Golf & Country Club: Enjoy scenic trails and lush surroundings while exploring the natural beauty of this region's outdoor spaces.
  • Visit the Saint Leo Abbey: Immerse yourself in the tranquil atmosphere of this historic Benedictine monastery, a serene spot for reflection and architecture enthusiasts.
  • Exploring local golf courses: Tee off at some of the area's renowned golf courses that offer picturesque views and challenging fairways for enthusiasts of all skill levels.
  • Bird watching in nearby nature reserves: Discover diverse bird species in the region’s protected habitats, making it an ideal activity for nature lovers seeking a peaceful outing.

Other Places to Stay in Saint Leo, FL

Saint Leo Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature: Take advantage of the region's scenic parks and outdoor spaces to enjoy peaceful walks and wildlife spotting during your stay.
  • Plan Your Activities: Research nearby attractions and events that showcase the area's unique charm and cultural heritage for an authentic experience.
  • Utilize Nearby Amenities: Make the most of local shops, restaurants, and services to enhance your visit and support small businesses here.
  • Choose Comfortable Accommodations: Select well-reviewed vacation rentals that offer amenities suited to your needs for a relaxing and enjoyable stay in this destination.

Transportation Options

  • Local Taxi Services: Reliable taxi companies in the area offer convenient transportation options to explore Saint Leo and surrounding attractions with ease.
  • Public Transportation: Regional bus routes provide budget-friendly and accessible travel throughout this destination, making it simple to get around without a car.
  • Car Rentals: Numerous rental agencies nearby give you the flexibility to discover the region at your own pace, ideal for visiting local sights and outdoor activities.
  • Rideshare Apps: Convenient rideshare services operate here, offering quick and affordable routes for both short trips and longer adventures within the area.

Local Customs Options

  • Southern Hospitality: Visitors often notice the warm and welcoming attitude that reflects the region’s Southern traditions and friendly community spirit.
  • You might observe the significance of church gatherings and religious festivals that play a central role in community life here.
  • Community Events: Participate in local festivals and parades that celebrate the area's history and culture, offering an authentic regional experience.
  • Wildlife Appreciation: Respect for native wildlife and conservation efforts is common, especially given the region’s natural landscapes and outdoor recreational opportunities.

Frequently Asked Questions About Saint Leo?

2. How many vacation rentals have private pools in Saint Leo?

There are 5 vacation rentals with private pools near Saint Leo. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Saint Leo are best for families?

If you are looking for a family-friendly vacation home in Saint Leo, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Saint Leo:

4. How many Rentbyowner vacation rentals are available in Saint Leo?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 102 in the Saint Leo area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Saint Leo. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the property owner, so it’s best to review the specific listing details for each vacation rental. You can find this information in the booking terms or contact the host directly for clarification.

6. How do I verify the safety and cleanliness standards of a vacation rental in this destination?

Details regarding safety measures and cleanliness protocols are typically included in the property description or provided by the owner. Ensure you read these thoroughly and reach out to the host if you have any concerns before completing your reservation.

7. Are there any additional fees or charges associated with booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are often listed in the rental listing. It’s recommended to review these costs beforehand and contact the owner if you need further clarification.

8. What amenities are typically included in vacation rentals in this region?

Most vacation rentals offer essential amenities like Wi-Fi, kitchen facilities, and parking. For specific features such as pools or outdoor spaces, check the property listing details or contact the owner directly to ensure your needs are met.

9. How far in advance should I book my vacation rental in this part of Florida?

It’s advisable to reserve your stay well in advance, especially during peak travel seasons. For the best availability and rates, consider booking at least several weeks ahead and confirm all details directly with the property owner.

Saint Leo Top Rated Vacation Rentals

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Hotel
Map-icon
like-icon8.6
Fabulous
(177 Reviews)
1 Bath 344.44 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R1,976/Night 7 Nights - R13,840
New
House
Map-icon
4 Bedrooms 2 Baths 4 Guests 150.69 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R2,941/Night 7 Nights - R20,589
House
Map-icon
2 Bedrooms 1 Bath 8 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R2,745/Night 7 Nights - R19,216
Hotel
1 Bath 602.78 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R1,634/Night 7 Nights - R11,438
House
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
3 Bedrooms 3 Baths 6 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R5,563/Night 7 Nights - R38,939
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 3 Baths 8 Guests 2600 ft²
  • Spa
    Spa
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R3,981/Night 7 Nights - R27,860
Other
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like-icon9.6
Exceptional
(20 Reviews)
4 Bedrooms 2 Baths 10 Guests 1717 ft²
  • Private Pool
    Private Pool
  • Fireplace/Heating
    Fireplace/Heating
More amenities
R6,838/Night 7 Nights - R47,861
House
Map-icon
like-icon9.0
Exceptional
(14 Reviews)
3 Bedrooms 2 Baths 6 Guests 1600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
R4,392/Night 7 Nights - R30,753