Holiday houses in Casselberry
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Top-rated holiday rentals in Casselberry
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10 min to Winter Park, Games, Gym, King bd, Coffee
Modern 3‑bed, 2 bath family retreat less than 30 minutes to Disney & Universal, 8 min to chic Winter Park. Spread out in the open‑plan living/dining, cook in the chef’s kitchen, binge board games or 1,000+ LEGO bricks, curl up with books, or crush a workout in the garage gym (rower, rack, bench, free weights). King suite + kids bunk w/ slide + queen sofa. Backyard play‑park, trampoline, swings, grill & shaded picnic. Fast Wi‑Fi, smart TV, espresso bar, parking. Ideal for families & work‑cations.
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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
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Clean, cozy home in a GREAT location
This clean, comfortable home is in a peaceful neighborhood and centrally located to everything you may wish to enjoy while on your Central Florida vacation. Literally two to three minutes away from I-4, highway 417 and a multitude of shopping and dining options. Universal Studios, Sea World and Daytona International Speedway are all within about 40 minutes, while Disney World and Kennedy Space Center are about 50 - 60 minutes. Also easy access to Sanford and Orlando International Airports.
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Cozy 4/2, King Beds, Pergola & Hot Tub, Local Pool
Newly renovated farmhouse gem centrally located in the beautiful Casselberry / Orlando area. Stylish and thoughtful touches throughout will make you feel right at home. 2 king beds, 1 queen and 1 bunk room (2 doubles & 2 twins) along with an 8' farmhouse table (seats 8) makes this home great for both small & larger groups alike. Complete with a hot tub, amazing walk-in shower, Marvel Arcade, Private patio with pergola outdoor furniture & gas grill, it's great for both the adults and kiddos!
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The Secret Sanctuary in Sanford, 5min from Airport
Welcome to your quiet, spacious, and private sanctuary. Enjoy all new appliances in the full size kitchen, a 50” flat screen TV, and a shaded outdoor area surrounded by greenery. It is located only minutes from the Orlando Sanford International Airport, Historic Downtown Sanford’s restaurants and shops, Lake Monroe’s scenic waterfront, and is centrally located between Florida’s beaches and the amusement parks. **Space is cleaned with EPA approved cleaners, including high touch surfaces**
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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
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"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.
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Pvt Fishing lk , Pets,Nature, Pool,garage
No HOA. Private 20 acre lake property, with fishing boats and trolling motors, canoes , peaceful boardwalk / dock. Large extra parking for trailers or work trucks. Fishing gear / poles. 2 car garage for safely storing whatever you bring. Fishing gear, tools, bikes, Harley's. Located near Seminole Trail, parks, sun-rail station. 45-60 min from the beach or the attractions DISNEY, UNIVERSAL STUDIOS, close to Lake Mary, Sanford, Wekiva Springs, Daytona 500, Bike week, 20 min from Boombah
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Gem Vacation Winter Park
Welcome to this luxury private pool home in Winter Park area ,thoughtfully designed for comfort,privacy,and style.Perfect for families or groups of to 8 guests ,this upscale retreat offers an exceptional stay in one of central Florida's most desirable neighborhoods. The home features spacious interiors,elegant decor,and high-end finishes,creating a refined yet welcoming atmosphere.Enjoy your own private swimming pool ,ideal for relaxing after a day exploring the area
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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!
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The Cypress House
This beautiful 2 bedroom, 1 bathroom Ranch Style home is conveniently located 3.5 miles from the Sanford International Airport and Boombah Sports Complex. The inviting landscape and backyard where you can cool off in the rustic style stock tank pool or grill out and relax on the patio. The open floor plan creates a spacious feel and every finish was selected with care. For a glamping experience check out our other listing: https://abnb.me/z3XrgOSPNFb
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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!!
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Popular amenities for Casselberry holiday rentals
Other great holiday rentals in Casselberry
Luxurious Lakefront Home | Near DT & Winter Park
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Modern Winter Park 2BR Near Park Ave Sleeps 6
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Moxy Luxe Vacation /Heated Pool /Last-Minute Deals
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Wana Chill Spot *Pool *Spa *Bar *Ping Pong *BBQ
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Luxury Villa: Heated Pool · Disney & Epic Universe
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3BD in Winter Park, 10 min Park Ave/Rollins, Pets
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Generations Gateway (Pool/Sauna)
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Garden Cottage Swim/Spa, Ctrl Orlando, Disney, 2/2
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When is the best time to visit Casselberry?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $192 AUD | $187 AUD | $201 AUD | $180 AUD | $177 AUD | $168 AUD | $161 AUD | $172 AUD | $170 AUD | $172 AUD | $187 AUD | $194 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.
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 $28 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!
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