Holiday houses in Casselberry
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Quick stats about holiday rentals in Casselberry
Total holiday rentals
Explore 140 holiday rentals in Casselberry
Nightly prices starting at
Casselberry holiday rentals start at $29 AUD per night before taxes and fees
Verified guest reviews
Over 4,970 verified reviews to help you choose
Family-friendly holiday rentals
80 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 40 rentals that welcome pets
Holiday rentals with a pool
60 properties feature pools
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Wi-Fi availability
140 of Casselberry holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Casselberry rentals
4.8 Average rating
Casselberry stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated holiday rentals in Casselberry
Guests agree: these stays are highly rated for location, cleanliness and more.
Comfortable and quiet place
Forget your worries in this spacious and serene space, we offer our guests k cups coffee(Victor Allens), sweteners (splenda) and "Oasis Bliss" personal care amenities( shampoo,conditioner, body lotion, bar soap).Private kitchen and bathroom. Also located less than an hour to Disney and Universal parks. Many restaurants and shoping centers around the area, 15 miles- 20 mins to "Orlando Sandford International Airport". Feel free to ask questions and our family will be in contact with you, thanks
July Specials, summer fun. Long term ok
Remodeled, modern and spacious 3-bedroom home in the Orlando area. Perfect for a weekend trip to the parks or a family vacation! ✨Fully Remodeled ✨Modern Design ✨Fully Stocked Kitchen ✨Close to Wekiva Springs ✨Private Fire Pit Area ✨Short Drive to the Beach ✨Short Drive to Disney World and Universal Studios! ✨Close to Orlando Airport ✨Reliable High Speed Wifi ✨Smart TV's ✨Outdoor Grill ✨Patio ✨Easy Freeway Access ✨Quiet Neighborhood ✨Insurance Displacement Stays Welcome ✨Long Term Stays Welcome
Winter Park Guest Suite |near UCF/FullSail/Rollins
🏠Look no further than this newly constructed guest suite. It's located in a centrally located neighborhood in Winter Park just a short drive from UCF, Rollins College, Full Sail, and Park Avenue. The guest suite is attached to the main house; however, it has its own private entrance. Our guest suite was constructed with impeccable design and high-end finishes throughout. We hope you will get to enjoy! 📌Please note: There’s no stove; however, there is a cook-plate with two burners to cook on.
Modern Winter Park 2BR Near Park Ave Sleeps 6
Welcome to our peaceful modern 2 bedroom 2 bathroom Winter Park home, just minutes from Park Ave. Perfect for summer trips, family visits, couples, small groups, or work stays. Our home is located in Winter Park, close to many of Orlando’s top attractions: * Universal Studios: about 14 miles * Walt Disney World: about 28 to 29 miles * Orlando International Airport: about 14 miles After exploring Winter Park, Park Ave, or Orlando attractions, come back to relax, cook, work, and recharge.
Pool, Hot Tub, Massage Chair, Golf, & Music Vibes!
Immerse yourself in a symphony of experiences at our uniquely themed home! Each of the four bedrooms celebrates a different music genre, creating a nostalgic journey. Perfect for up to 14 guests, this spacious family retreat features a private pool, hot tub, games, putt-putt, record player, soccer, and an outdoor grill. After booking, you’ll receive a link to the agreement with house rules posted in the listing. FYI - we love our trees and bamboo for privacy, but leaves will be in the pool.
Villa with Guest House & Pool-Patio
Welcome to this Amazing House Pool-Patio with 4 Bedrooms + 2 Bathrooms and optional guest house to complete the 10 guests. True gem with covered summer kitchen, covered pergola, garage for two cars and a large driveway. 30 Minutes distance to Universal, Sea World, Volcano Bay and others. UCF in 15 minutes and Daytona beach/Cape Canaveral in 50’. Great restaurants and shops. The house is conveniently located for all attractions in Central Orlando. Airport is 25 minutes. SAFE NEIGHBORHOOD
"Winnie's Place" A Peaceful Guesthouse with Pool.
Share the quiet yard and pool with hosts. 1 hr. from Disney & the beaches. 12 yr & older only. Single Sofa bed for 3rd guest. NOT a heated pool. Not Handicap Certified, but most wheelchair guests have not had issues. Narrowest opening 32" Ramp into unit by pool. Shower no steps. Queen bed height 29"-standard cabinets. Grab bars in bathroom. Airbnb's Accessibility Policy has exempted this listing from accepting Service & Emotional Support Animals due to owner's severe health condition.
Charming Private Lakefront Cottage Retreat
You can fully relax in this adorable lakefront cottage. We're sure you'll enjoy all of the wonderful amenities this peaceful property has to offer. Our incredibly unique cottage is nestled under a large grand oak tree and tucked away behind climbing jasmine vine clad fencing and security gates. Inside, you will find a new remodeled fully stocked kitchen and luxury bathroom. Our cozy cottage has all the comforts of home and more. Reserve your stay today and enjoy this special property.
Cozy Modern Studio
This private studio has been converted from a garage to a fully equipped studio. A spacious open-concept layout with everything in one stylish and functional space. It features a comfortable sleeping area, a fully equipped kitchen, a private bathroom, and an in-unit washer and dryer—perfect for solo travelers, couples, or digital nomads looking for a quiet, well-equipped place to call home. Disney world - about 1hr Universal studios- about 40min Boombah sports plex - about 25 min
Winter Park Pearl 6 min drive to historic Park Ave
This Winter Park cottage was built in 1954 with original hardwood flooring. Take a 5 min drive to and through historical Winter Park to access shops and restaurants on the coveted Park Ave. It is the perfect central location to access beaches, Universities, Orlandos events, and the best restaurants. The house is tucked away into a quiet neighborhood with lots of sleepy old big oaks. If you have any questions I am always available, so please ask. My response time is immediate!
Luxury Villa: Heated Pool · Disney & Epic Universe
Perfect for families & groups — The Blue Villa! Sleeps 8: King, Queen, Twin, Trundle + Folding bed Heated private pool 24 hrs + BBQ Fully equipped kitchen Wi-Fi 1Gbs - 3 Smart TVs Free parking 4 cars + EV Charger L2 Home gym: elliptical & stationary bike Game room: ping pong, billar, darts, etc Private patio - quiet & safe area Workstation - in-unit laundry 24/7 Superhost support 30 min to Disney, Epic Universe & MCO Airport Self check-in via keypad. Make yourself at home!
Entire Townhome | Stylish & Cozy | Peaceful
Bring the whole family and make this your home away from home. This townhome is equipped with everything needed to make your stay comfortable and feel at home. From washer and dryer, to a kitchen with everything needed to cook your meals. Parking is right in front of the townhome and the outdoor space can be used to relax and enjoy some quiet time. We are also roughly 30 minutes away from Universal and 40 from Disney for your park adventures!!
Popular amenities for Casselberry holiday rentals
Other great holiday rentals in Casselberry
The Tiny Cottage in the Springs/ Central FL
Top 1% Modern Japandi Retreat - Jacuzzi No Fee
Nook Ave Studio| Priv Patio| Pool & Hot Tub Access
Wana Chill Spot *Pool *Spa *Bar *Ping Pong *BBQ
Spacious 3 BR Home Perfect for Orlando Getaway
The Winter Park Experience
Sunshine Villa Stay
Cozy Winter Park Retreat
When is the best time to visit Casselberry?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $196 AUD | $190 AUD | $205 AUD | $183 AUD | $180 AUD | $171 AUD | $164 AUD | $176 AUD | $173 AUD | $176 AUD | $190 AUD | $198 AUD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Frequently Asked Questions
What are the best places to stay in Casselberry?
Vacation rentals in Casselberry are found in neighborhoods near parks and lakes, making it easy to access outdoor activities. Family homes and apartments are popular choices for groups and longer stays.
What are the best things to do in Casselberry with kids?
Families often explore parks with playgrounds, lakes for birdwatching, and community recreation centers in Casselberry. Seasonal festivals and craft spaces are frequently suggested for hands-on fun.
What are some of the best things to do in Casselberry?
Explore lakeside parks, try craft workshops at community centers, or attend outdoor concerts with local musicians. Art fairs and food markets are also popular throughout the year.
How is the weather in Casselberry?
Casselberry has mild winters around 49–72°F (10–22°C) and warm, humid summers near 74–92°F (23–33°C), with higher rainfall in summer months. Lightweight clothing and a rain jacket are recommended.
When is the best time to visit Casselberry?
Late winter through spring is often recommended, with pleasant temperatures and blooming landscapes. Outdoor festivals and farmers markets are common in these months.
What are the best places to visit in Casselberry?
Frequently suggested spots in Casselberry include local parks, art galleries, and lakeside recreation areas. The city has community gardens and public spaces hosting events throughout the year.
What are some hiking trails in Casselberry?
Casselberry's parks have walking and biking trails around lakes and wooded areas that are frequently suggested for leisurely hikes. Community paths make it easy to enjoy the city’s natural scenery.
What are some family activities we can do in Casselberry?
Families can enjoy playgrounds at local parks, paddle on lakes, or participate in art workshops at community spaces. Storytime events and public concerts are often recommended for a lively day out.
What are some of the best day trip ideas from Casselberry?
Day trips from Casselberry often include exploring nature preserves, visiting local art museums, and discovering larger city attractions around the region. Botanical gardens and historic districts are frequently suggested within reach.
Are there any pet friendly accommodations available in Casselberry?
Many vacation rentals in Casselberry welcome pets, especially in areas near parks and lake walking paths. The city has green spaces for outdoor time with dogs and other pets.
What are some local tips for visiting Casselberry?
Locals often suggest bringing comfortable shoes for lake park walks and checking community calendars for art fairs and concerts. Independent cafes and shops around the city provide a welcoming atmosphere.
What is Casselberry known for?
Casselberry is known for its scenic lakes, community parks, and annual arts and music festivals. The city also has a strong tradition of outdoor recreation and neighborhood gatherings.
What are the best hidden gems to explore in Casselberry?
Casselberry has small neighborhood gardens, mural-lined walking paths, and lakes often mentioned by locals for a peaceful retreat. Family-run eateries and independent shops add distinct flavor to the area.
What are the best foods to try in Casselberry?
Casselberry has a mix of Southern-inspired dishes, Latin American flavors, and locally baked desserts. Independent restaurants and food markets often showcase regional favorites and fusion cuisine.
What should I bring for a trip to Casselberry?
Pack lightweight clothing, sunscreen, and a rain jacket for summer, as humidity and quick showers are common. Comfortable walking shoes and insect repellent are also suggested for outdoor activities.
What is the nightlife in Casselberry like?
Casselberry has a relaxed nightlife with neighborhood bars, live music venues, and casual eateries. Community events and local performances bring people together in the evenings.
What are the most popular events or festivals in Casselberry?
Casselberry hosts annual arts and music festivals, food-centric events, and cultural celebrations during spring and fall. Outdoor concerts and holiday gatherings are also frequently suggested.
Are there family friendly vacation rentals in Casselberry?
Casselberry has a range of vacation rentals, including homes and apartments well-suited for families. Many accommodations are located near parks, shopping, and local activities.
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- Family-friendly rentals Casselberry
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Daytona International Speedway
- Magic Kingdom Park
- Camping World Stadium
- Epcot
- Universal's Volcano Bay
- Kia Center
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- University of Central Florida
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- ESPN Wide World of Sports
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