Calimesa vacation rentals

We found 184 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Calimesa to find one that's perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the amenities you need and want for your stay, including air conditioning and cable TV. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

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Find out more about Calimesa

Why visit Calimesa

  • Outdoor Adventures: Calimesa is perfect for family-friendly outdoor activities, with plenty of parks and natural attractions.
  • Charming Neighborhoods: Explore nearby Cherry Valley, featuring local shops and a welcoming atmosphere.
  • Diverse Accommodations: Choose from cozy cabins, spacious homes, and modern condos to suit any traveler's needs.
  • Cultural Experiences: Engage with local colleges, universities, and event venues for enriching cultural activities.
  • Proximity to Beaches: Enjoy easy access to nearby beaches, perfect for relaxation and fun in the sun.

Popular types of accommodation in Calimesa

Planning a getaway to Calimesa? You've picked a fantastic destination. Explore a variety of popular vacation rentals, including cozy cabins, spacious private homes, and modern condos. Whether you're searching for a 2-bedroom home or an affordable apartment, Calimesa offers options to fit every traveler's needs. Discover the perfect place to unwind and create lasting memories in this charming city.

  • Cabins: The top choice for vacation rentals in Calimesa, offering a cozy escape surrounded by nature.
  • Houses: A popular option for families and groups, providing ample space and comfort.
  • Condos: Ideal for those seeking modern amenities and a community feel during their stay.
  • Apartments: A convenient choice for travelers looking for a stylish and practical home base.
  • Cottages: These charming accommodations offer a quaint and inviting atmosphere for a relaxing getaway.**

Top attractions near Calimesa

Calimesa, California, is perfect for family getaways and outdoor adventures. Visitors can explore a variety of attractions, including modern colleges and universities, event venues, and nearby beaches. Whether you're seeking cultural experiences or just want to enjoy the great outdoors, Calimesa offers plenty of options to create lasting memories during your vacation.

  • National Orange Show Events Center: A vibrant venue located 15 miles from Calimesa, this center hosts a variety of events and exhibitions, showcasing local culture and business. Its bustling atmosphere makes it a hub for networking and entertainment.
  • University of Redlands: Situated 7 miles away, this modern university offers a picturesque campus with impressive architecture and a lively student atmosphere, perfect for strolling and exploring its gardens and cultural events.
  • Wildwood Canyon: Just 4 miles from Calimesa, this state park is a haven for outdoor enthusiasts, featuring scenic hiking trails, breathtaking views, and opportunities for adventure amidst nature.

Things to do recommended for couples

For a romantic getaway in Calimesa, consider a day of skiing at Snow Valley Mountain Resort, only 14 miles away, or the scenic Rim Nordic Ski Area, 15 miles distant. Enjoy the thrill of winter sports together, surrounded by beautiful mountain views.

Things to do recommended for families

Families can unwind at Yucaipa Regional Park, just 3 miles away, enjoying its serene atmosphere. For sports enthusiasts, the San Bernardino Soccer Complex, 13 miles away, offers exciting matches. Round1 Bowling & Amusement, also 13 miles from Calimesa, guarantees fun-filled adventures with bowling and arcade games.

Things to do recommended for groups

In Calimesa, groups can enjoy a round of golf at Oak Valley Golf Club, just 5 miles away. For shopping and dining, The Village and Lake Arrowhead Village, both 19 miles away, offer vibrant experiences with family-friendly atmospheres and plenty of entertainment options.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Calimesa

When traveling with a group, family, pets, or planning for extended stays, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Calimesa with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Calimesa with young kids: Traveling with little ones can be tough. It’s important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Calimesa: For many families, a vacation isn’t truly enjoyable without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Calimesa: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Calimesa

Calimesa, California, is a charming destination perfect for family-friendly outdoor adventures and urban excursions. Explore nearby Cherry Valley and its inviting neighborhoods, where you can enjoy a blend of local shopping centers and friendly atmospheres. Whether you're seeking a romantic getaway or a business-friendly environment, Calimesa offers a delightful mix of experiences that cater to all types of travelers. Discover the warmth of this community as you embark on your vacation.

  • Yucaipa: Nestled just 3 miles from Calimesa, Yucaipa offers a vibrant family-oriented atmosphere with plenty of outdoor activities. This charming city features an array of recreational areas perfect for picnics and sports, along with shopping centers for those seeking retail therapy. Notable attractions include a local theme park and various event venues that host conferences and community gatherings. Yucaipa’s scenic parks provide a picturesque backdrop for hiking and relaxation, making it an ideal destination for families and outdoor enthusiasts alike.
  • Redlands: Located 8 miles from Calimesa, Redlands is a picturesque city known for its historic charm and vibrant community. Travelers flock to Redlands for its blend of family-friendly and romantic experiences. The city boasts several shopping centers and a sprawling mall, perfect for leisurely afternoons. Visitors can explore local landmarks such as a popular stadium and a lively theme park, while also enjoying educational attractions that enrich their travel experience. Redlands’ beautiful tree-lined streets and inviting atmosphere make it a delightful stop on your vacation.
  • San Bernardino: As a bustling metropolis that encompasses Calimesa, San Bernardino offers a diverse range of experiences for visitors. Travelers can immerse themselves in the city's rich culture while enjoying family-friendly attractions such as recreational areas and educational venues. The city is home to numerous shopping centers, providing a great way to unwind and shop. With key landmarks like stadiums and theme parks, San Bernardino is perfect for both business travelers and families looking for exciting activities. Experience the vibrant urban life and welcoming community during your stay.

Best time to go to Calimesa

If you're planning a trip to Calimesa, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and July, while off-peak times, like August and December to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January48.2°F (9.0°C)Light RainSunnySlightly LowSlightly High
February48.9°F (9.4°C)Light RainSunnyAverageSlightly High
March52.5°F (11.4°C)No Rain (Dry)Mostly SunnySlightly HighAverage
April58.3°F (14.6°C)No Rain (Dry)SunnySlightly HighSlightly Low
May62.8°F (17.1°C)No Rain (Dry)SunnyAverageSlightly Low
June71.6°F (22.0°C)No Rain (Dry)SunnyAverageAverage
July78.8°F (26.0°C)No Rain (Dry)SunnySlightly HighAverage
August79.2°F (26.2°C)No Rain (Dry)SunnySlightly LowAverage
September74.7°F (23.7°C)No Rain (Dry)SunnyAverageAverage
October64.4°F (18.0°C)No Rain (Dry)SunnyAverageSlightly Low
November54.5°F (12.5°C)No Rain (Dry)SunnyAverageAverage
December47.5°F (8.6°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can help, as prices often vary. Additionally, booking a longer stay typically leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board feature offers you a convenient way to plan your travels. You can start new trips, pick up where you left off, or easily view and organize your travel plans. All the properties you’ve saved and booked are now neatly categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Head to the lively city of Calimesa

Enjoy the live music and other features of Calimesa. This welcoming city is known for its restaurants, casino gaming and shopping. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Calimesa

Are you hoping to discover attractions to visit while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Calimesa a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Oak Valley Golf Club (5.2 mi / 8.3 km)
  • Snow Valley Mountain Resort (14.6 mi / 23.4 km)
  • Soboba Springs Country Club (15.9 mi / 25.6 km)
  • Big Bear Mountain Resort (16.8 mi / 27 km)
  • Perris Auto Speedway (13.3 mi / 21.4 km)
  • Fiesta Village Family Fun Park (14.2 mi / 22.8 km)

Exploring the natural features in Calimesa

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Calimesa. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Yucaipa Regional Park (3.4 mi / 5.5 km)
  • Lake Perris State Recreation Area (11.8 mi / 19 km)
  • Lake Perris (12.1 mi / 19.5 km)
  • San Bernardino Soccer Complex (13.1 mi / 21.2 km)
  • The Lincoln Memorial Shrine (7.8 mi / 12.6 km)
  • Moreno Beach (11.2 mi / 18 km)

How to get to and around Calimesa

The nearest airport is in San Bernardino, CA (SBD-San Bernardino Intl.), located 12.5 mi (20.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Murrieta, CA (RBK-French Valley), which is 29.8 mi (48 km) away.

Frequently asked questions

What is the best area to stay in Calimesa, California, United States of America when booking a vacation rental?
When considering a vacation rental in Calimesa, California, the area around the city center offers a charming and convenient experience. This neighborhood provides easy access to various local attractions, making it an ideal choice for visitors. One of the standout points of interest is the beautiful Calimesa Country Club, which features stunning landscapes and is great for golf enthusiasts. Additionally, the nearby San Jacinto Mountains offer breathtaking views and opportunities for outdoor activities such as hiking and nature walks.

In the city center, you'll find a mix of vacation rental options that cater to different preferences and budgets. Staying here not only places you within reach of these attractions but also allows you to enjoy the small-town charm of Calimesa, with its friendly atmosphere and local eateries.
How much does it cost to rent a vacation home in Calimesa?
Prices for vacation rentals in Calimesa vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Calimesa to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Calimesa vacation house rentals?
You can find great discounts on house rentals in Calimesa on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Calimesa?
In Calimesa, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These properties often provide spacious living environments suitable for families or larger groups, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation. Many vacation houses are situated in quiet neighborhoods, offering a peaceful retreat while still being conveniently located near local parks and recreational areas, making them ideal for travelers looking to enjoy the natural beauty of Southern California.
Can I find long-stay vacation rentals in Calimesa?
A long-stay vacation rental in Calimesa is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Calimesa?
In Calimesa, travelers will find several pet-friendly house rentals that cater to those looking to enjoy a comfortable stay with their furry companions. The area offers a variety of amenities in these properties, including spacious backyards, fully equipped kitchens, and cozy living areas, which create a welcoming environment for families and their pets.

Calimesa is conveniently located near several parks and recreational areas that are ideal for pet owners. The nearby Calimesa Community Park features open green spaces and walking paths where pets can enjoy some exercise and playtime. Additionally, the surrounding natural landscapes provide opportunities for outdoor adventures, making it a great destination for pet-friendly vacations.
Are there any Calimesa vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Calimesa with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Calimesa?
In Calimesa, popular vacation rental amenities include pet-friendly options, allowing travelers to bring their furry companions along for the trip. Many rentals accommodate service animals as well, ensuring a comfortable stay for guests who may need assistance. These amenities cater to families and solo travelers looking for a welcoming environment while enjoying the area's attractions and natural beauty.
When is the best time to visit Calimesa for a vacation rental?
The best time to visit Calimesa for a vacation rental is during the peak season from March to May. This vibrant period welcomes travelers eager to enjoy the beautiful California spring, where outdoor activities like hiking and golfing flourish under sunny skies. With temperatures ranging from the mid-50s to the low 80s Fahrenheit, this time of year offers a pleasant climate that is superb for exploring the scenic landscapes and local attractions.

March stands out as a particularly popular month, as visitors can take advantage of blooming wildflowers and comfortable weather while engaging in various outdoor pursuits. Whether you're looking to stroll through local parks or embark on a scenic drive, the stunning surroundings make for a memorable experience.

For those seeking a more budget-friendly option, consider visiting in January. While this month is quieter, it provides a peaceful atmosphere ideal for relaxation and introspection, allowing you to enjoy the natural beauty of the area without the hustle and bustle of peak season.

Ultimately, your choice of when to visit Calimesa will depend on your preferences for lively spring activities or a tranquil retreat during the quieter months.
How early should I book a Calimesa vacation rental?
Book your Calimesa vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Calimesa, California, United States of America?
In Calimesa, visitors can enjoy a range of attractions that highlight the area's natural beauty and community spirit. The Yucaipa Regional Park, located nearby, offers a wonderful setting for outdoor activities including hiking, fishing, and picnicking, making it a popular spot for families and nature enthusiasts. The park features serene lakes and scenic trails, providing a great escape into nature.

In town, the Calimesa Historical Society Museum offers insights into the local history and culture, showcasing artifacts and exhibits that celebrate the community's heritage. For those interested in golf, the Calimesa Country Club is a popular destination, featuring a scenic course that caters to both beginners and experienced golfers.

Additionally, Calimesa's proximity to the San Bernardino National Forest allows for easy access to further outdoor adventures, including hiking and camping in the beautiful mountainous terrain.
Can I change or cancel my Calimesa home rental booking on Vrbo?
To find Calimesa vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Calimesa vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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