House
10.0(41 Reviews)
1 Bedroom
2 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $145/Night
7 Nights - US $1,017
Saint Leo Holiday Rentals
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Compare Villas, Resorts, & Rentals in Saint Leo
10.0
House
10.0(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
Internet
Child Friendly
US $121/Night
7 Nights - US $849
US $452/Night
7 Nights - US $3,161
Cottage
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $281/Night
7 Nights - US $1,967
House
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $219/Night
7 Nights - US $1,535
House
10.0(5 Reviews)
2 Bedrooms
6 Guests
Private Pool- Parking
Pool- Balcony/Terrace
US $187/Night
7 Nights - US $1,312
House
10.0(4 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $163/Night
7 Nights - US $1,142
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $272/Night
7 Nights - US $1,905
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $441/Night
7 Nights - US $3,086
Luxury Holiday Rentals in Saint Leo
Over 107+ Luxury Holiday Rentals in or Near Saint Leo
House
10.0(6 Reviews)
6 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,401/Night
7 Nights - US $9,806
US $1,132/Night
7 Nights - US $7,927
House
3 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,117/Night
7 Nights - US $7,821
House
9.2(7 Reviews)
5 Bedrooms
18 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,078/Night
7 Nights - US $7,544
New
Bed & Breakfast
7 Bedrooms
25 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $890/Night
7 Nights - US $6,231
New
Other
5 Bedrooms
11 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $724/Night
7 Nights - US $5,067
New
Villa
10.0(12 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $717/Night
7 Nights - US $5,020
House
1 Bedroom
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $636/Night
7 Nights - US $4,455
Villa
10.0(12 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
Ocean View
US $616/Night
7 Nights - US $4,309
Top-Rated Holiday Rentals with a Pool in Saint Leo
Over 23+ The Best Private Villas and Holiday Rentals in Saint Leo with a Pool
Other
10.0(1 Review)
4 Bedrooms
16 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $574/Night
7 Nights - US $4,016
Villa
10.0(1 Review)
3 Bedrooms
8 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $474/Night
7 Nights - US $3,318
House
10.0(1 Review)
4 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $256/Night
7 Nights - US $1,790
US $128/Night
7 Nights - US $894
Hotel
8.6(177 Reviews)
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
US $175/Night
7 Nights - US $1,227
House
7.0(4 Reviews)
5 Bedrooms
18 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $589/Night
7 Nights - US $4,122
House
1.0(1 Review)
4 Bedrooms
4 Guests
Oceanfront- Parking
- Pool
- Ocean View
US $180/Night
7 Nights - US $1,260
New
House
3 Bedrooms
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $163/Night
7 Nights - US $1,141
House
10.0(11 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $562/Night
7 Nights - US $3,931
Pet-Friendly Holiday Rentals in Saint Leo
Over 31+ Pet-Friendly Holiday Rentals in or Near Saint Leo
Cottage
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $202/Night
7 Nights - US $1,412
House
8.0(3 Reviews)
5 Bedrooms
10 Guests
- Parking
- Internet
- Pet Friendly
Security/Safety
US $233/Night
7 Nights - US $1,631
House
10.0(56 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
View- Kitchen
US $225/Night
7 Nights - US $1,576
House
8.0(1 Review)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $189/Night
7 Nights - US $1,320
House
9.8(33 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $245/Night
7 Nights - US $1,717
House
9.0(7 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $204/Night
7 Nights - US $1,428
House
8.0(2 Reviews)
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $299/Night
7 Nights - US $2,095
House
3 Bedrooms
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $562/Night
7 Nights - US $3,937
New
House
4 Bedrooms
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $484/Night
7 Nights - US $3,386
Large Holiday Rentals and Private Villas in Saint Leo
Over 17+ Large Holiday Rentals and Private Villas in or Near Saint Leo
House
5 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $316/Night
7 Nights - US $2,215
US $113/Night
7 Nights - US $788
Villa
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $239/Night
7 Nights - US $1,675
US $343/Night
7 Nights - US $2,401
House
8.4(7 Reviews)
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $302/Night
7 Nights - US $2,116
House
7 Bedrooms
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,111/Night
7 Nights - US $7,774
House
4 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $447/Night
7 Nights - US $3,130
House
5 Bedrooms
10 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $396/Night
7 Nights - US $2,775
House
3 Bedrooms
10 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $358/Night
7 Nights - US $2,509
Wheelchair Accessible Holiday Homes in Saint Leo
Over 1+ Wheelchair Accessible Holiday Homes in or Near Saint Leo
New
Hotel
3.0(1 Review)
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $83/Night
7 Nights - US $581
Saint Leo Private Villas and Holiday Homes Under $200
Over 26+ Saint Leo Private Villas and Holiday Homes Under $200
New
House
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $96/Night
7 Nights - US $670
House
8.0(1 Review)
3 Bedrooms
6 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
US $188/Night
7 Nights - US $1,319
US $69/Night
7 Nights - US $486
Apartment
1 Bedroom
3 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $186/Night
7 Nights - US $1,303
US $187/Night
7 Nights - US $1,309
House
9.6(136 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $84/Night
7 Nights - US $588
House
2 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $188/Night
7 Nights - US $1,314
House
1 Bedroom
4 Guests
- Hot Tub
- Air Conditioner
- Child Friendly
- Laundry
US $125/Night
7 Nights - US $875
Apartment
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $122/Night
7 Nights - US $854
Instantly Bookable Holiday Homes in Saint Leo
Over 36+ Instantly Bookable Holiday Homes in or Near Saint Leo
House
10.0(1 Review)
1 Bedroom
2 Guests
- Child Friendly
US $220/Night
7 Nights - US $1,543
House
9.0(2 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $259/Night
7 Nights - US $1,814
Apartment
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $327/Night
7 Nights - US $2,290
House
10.0(4 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $301/Night
7 Nights - US $2,110
House
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $474/Night
7 Nights - US $3,319
House
9.4(8 Reviews)
3 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $427/Night
7 Nights - US $2,989
Condo
8.4(5 Reviews)
3 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $282/Night
7 Nights - US $1,972
New
House
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $404/Night
7 Nights - US $2,825
House
3 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $236/Night
7 Nights - US $1,652
Book a Last Minute Place to Stay in Saint Leo
About Casai's Private Villas and Holiday Rentals in Saint Leo
Discover more than 116 vacation rentals available in Saint Leo. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Saint Leo.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Saint Leo, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Saint Leo. On average, places to stay near Saint Leo offer 1943.27 ft², with nightly prices averaging US $355.
With Casai, finding and comparing holiday rentals in Saint Leo is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
There are 116 Saint Leo, FL Holiday Rentals
- Prices for a holiday home in Saint Leo start at US $69
- Top rated vacation home in Saint Leo is Whole House in San Antonio. Walking Distance to St. Leo University!
- Most popular short term in Saint Leo is Hampton Inn Dade City - Zephyrhills
- Cheapest place to stay in Saint Leo is Sunshine Motel Zephyrhills Dade City
- Most expensive holiday rental in Saint Leo is Dade City's Historic 1892 Locke Inn Estate
Recently Booked Holiday Rentals in Saint Leo
Frequently Asked Questions About Saint Leo?
What are the top holiday rentals in Saint Leo?
With numerous options available in Saint Leo, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Saint Leo:
- Whole House in San Antonio. Walking Distance to St. Leo University!
- Private Suite
- Elegant 3BR Lake Jovita Golf Villa St. Leo Access
- Wake up on the 18th green at Lake Jovita, DISCOVER YOUR IDEAL GOLF RETREAT
- The Historic Sweetwater Cottage Firepit & Cornhole
- Dade City's Historic 1892 Locke Inn Estate
- Peaceful Home Retreat with Pool Near St. Leo University and Mirada Lagoon
- Downtown Dade City Glamper
- Newly Renovated Modern Home 1-Acre Retreat 86”TV Firepit King Bed 3CarPark Lanai
- Enjoy the Pleasures of Historic Downtown Dade City- The Dade City Bungalow
How many holiday rentals have private pools in Saint Leo?
Discover a selection of holiday rentals with private pools near Saint Leo with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Saint Leo are best for families?
If you're searching for a family-friendly holiday home in Saint Leo, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Saint Leo:
How many Casai.com holiday rentals are available in Saint Leo?
As of 2026, Casai boasts over 116 properties listed in the Saint Leo area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Saint Leo.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Lake Jovita Vacation Rentals in Port Richey, Florida | 28 |
