Holiday rentals in Casselberry

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Top-rated holiday rentals in Casselberry

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A charming pathway made of light-colored bricks leads to the entrance of a compact guest studio. Lush greenery, including tropical plants and palm trees, surrounds the area, enhancing the inviting atmosphere. Natural sunlight brightens the facade, complemented by textured wooden accents on the side.
Guest house in Sanford
4.94 out of 5 average rating, 262 reviews

Private Courtyard Cottage on Canal

Enjoy a comfortable stay in this private guest cottage with its own entrance, detached from the main house—perfect for privacy and relaxation. Features an extremely comfortable king-size bed, TV, and WiFi ideal for streaming or remote work. The kitchenette includes a full-size fridge, microwave, sink, air fryer, and coffee maker for easy meals and morning coffee. Ideal for couples, solo travelers, business stays, or sports families looking for a quiet, comfortable home base close to everything

Top guest favourite
The exterior of the home features a welcoming front entrance with a gray door and arched window. The pathway is lined with colorful foliage, and tropical plants surround the entrance. A lamp post stands at the forefront, providing soft illumination amidst the lush greenery.
Home in Sanford
4.98 out of 5 average rating, 286 reviews

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.

Top guest favourite
A cozy living area features a dark gray sofa and armchair, complemented by a light rug on the floor. A small desk with a chair sits against the wall, and a wall-mounted television is positioned above. Natural light pours in through the front door with a window.
Flat in Orlando
5 out of 5 average rating, 233 reviews

Parent's Retreat!

Whether working in the area, visiting your student or catching a UCF Sporting event. This pet friendly "Parent's Retreat" is just what you're looking for. Located less than 2 miles from campus. this apartment is a great place to land at the end of the day. Kitchen includes microwave, fridge, coffee maker and air fryer. This 380 sq ft newly remodeled mother-in-law suite has private entrance, patio and yard. Suite is completely closed off from the house and has keyless locks for easy check in.

Superhost
A spacious living area features a large sectional couch and a stylish coffee table. Natural light filters through the windows, highlighting modern décor. An arcade game stands in the background, and a laundry area is visible to the left, contributing to the home's functionality.
Home in Casselberry
4.88 out of 5 average rating, 145 reviews

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!

Superhost
Home in Fern Park
4.81 out of 5 average rating, 111 reviews

Centrally Located Orlando Home

Enjoy this nice centrally located suburban Orlando home in quiet neighborhood near golf & outdoor activities. Walking distance to Kewanee park with nature trails, playground and wildlife. Just 15 mi to airport, 10 mi to dowtown, 20 mi to attractions, 35 mi to beaches & 3-8 mi to all local colleges. Near to tons of shopping, restaurants & nightlife. Nearby Publix, Winn Dixie, Walmart & Walgreens. Washer/ Dryer. Stainless appliances. Keurig & French press. Covered patio. Keyless entry.

Top guest favourite
A refreshing pool is captured, with sunlight sparkling on the water's surface. The stone-accented summer kitchen with a wooden pergola is visible in the background, along with plants and seating, creating a relaxed outdoor setting.
Home in Casselberry
4.93 out of 5 average rating, 132 reviews

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

Top guest favourite
A refreshing pool with stone borders is surrounded by lush greenery and shaded by a blue canopy. Comfortable seating for two is visible, along with a hammock, creating a serene outdoor space ideal for relaxation.
Guest house in Longwood
4.98 out of 5 average rating, 136 reviews

"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.

Top guest favourite
The image depicts a calm lake at sunset, with reflections of clouds and colors mirrored in the water. In the foreground, a fishing boat is anchored, positioned near the lake's serene shoreline surrounded by lush greenery.
Home in Longwood
4.95 out of 5 average rating, 168 reviews

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

Guest favourite
A spacious living area is highlighted by a brown sofa and a round dining table surrounded by wooden chairs. A ceiling fan circulates air while large windows provide natural light and views of the backyard. A television is mounted on the wall.
Guest suite in Casselberry
4.91 out of 5 average rating, 117 reviews

Orlando, spacious, quiet, centrally located, suite

This suite includes private entrance, living room, kitchen with utensils and cookware, one bedroom with king bed and private bath. Third and fourth persons may be accommodated with recliner that lays flat into a queen-size bed in living room. Also a queen size air mattress and portacrib is available. Excellent location for Disney, Universal, SeaWorld, and beaches. Approx. 35 min. to Disney; 27 min. to Universal; 23 min. to convention center; 45 min. to beach; and 35 min. to Airport.

Guest favourite
A modern kitchen area is visible, featuring white cabinetry and a dark granite countertop. A large flat-screen TV is mounted above a fireplace, while a geometric design adorns the wall. Stainless steel appliances are included, providing a stylish and functional cooking space.
Home in Altamonte Springs
4.87 out of 5 average rating, 121 reviews

Renovated Peaceful Luxury Walk to Mall Park Publix

- Luxury 2 Bedroom/1Bath Style Renovated peaceful home with Fireplace, Skylights, 87 inch TV, Chandelier, & Full kitchen - Spacious bathroom - Americans with Disabilities Act (ADA) bars for shower and toilet & Smart mirror - Outdoor Gym with Kids Playground & Dedicated Laundry Room - 1 minute drive to major highway Orlando ( Disney, Universal, Aquatica, Beaches, Downtown ) Approximately 30 minutes away - Plenty of free private parking right in front of the house - Pet friendly

Top guest favourite
A spacious bedroom features a large bed dressed in neutral tones, accented by decorative pillows. Natural light filters through angular windows, illuminating the space. A seating area with a gray bench is positioned at the foot of the bed, and wooden walls provide a warm backdrop.
Home in Longwood
4.98 out of 5 average rating, 133 reviews

Private 4-Bedroom home with pool!

Entire home located on 1 acre of land in the luxury neighbor hood of Markham Woods. This property is the ideal place to stay for a family vacation, or business trip. Take a swim in our large pool and enjoy the Florida Sun! Please add exact number of your guests, in your booking! Please NO Parties or gatherings! (Family visits are welcome 🤗) Please NO smoking on the property. If any violation occurs, your stay will be terminated immediately, and you will be charged a $1,500 fine!

Top guest favourite
Cottage in Winter Park
4.95 out of 5 average rating, 456 reviews

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!

Popular amenities for Casselberry holiday rentals

When is the best time to visit Casselberry?

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Avg. price£101£98£105£94£92£88£84£90£89£90£98£101
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°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 £15 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    140 of Casselberry holiday rentals include wifi 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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  5. Casselberry