Holiday houses in Casselberry

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Casselberry

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

1 of 1 pages1 / 1
Guest favourite
An outdoor seating area features blue Adirondack chairs and a patterned table, arranged on a concrete patio. Two large trees provide shade, and a swing is visible in the background. The space is accented with decorative rugs and greenery, fostering a relaxed atmosphere.
Home in Sanford
4.93 out of 5 average rating, 268 reviews

Farmhouse-Chic Retreat with a Charming Patio

Guests have full use of the house, including a spacious kitchen. Four bedrooms with memory foam mattresses ensure you can sleep comfortably. The dining room table can seat 6-8. In the living room there’s a comfortable seating area across the room from a large desk - great for those traveling for work! There is a separate laundry room off the back patio. Guests will have complimentary use of detergent. Iron and ironing board are also available for guest use. On the property there’s an occupied mother-in-law apartment - with separate parking and it’s own entrance so that guests staying in the house are not disturbed by the apartment’s full-time occupant. The backyard is also has a dividing fence for house guests’ privacy. As a guest staying at the house you will have privacy, but I’m local nearby and can assist guests at their request. Behind the house is an occupied apartment that has its own entrance, parking, and backyard. Nestled into a cluster of moss-draped oaks, the house is only a short drive from restaurants and shops in Lake Mary and quaint downtown Sanford. The best way to navigate the area is by car. There are several car rental agencies nearby, with the Orlando-Sanford International Airport just 5-7 min drive.

ValueLocationIndoor spaces

Guest favourite
A spacious bedroom features two sets of twin bunk beds, accommodating multiple guests. A cozy seating area with a chair and ottoman is positioned in front of a mounted TV. Large windows invite natural light, enhancing the bright, modern decor.
Home in Casselberry
4.92 out of 5 average rating, 87 reviews

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

FamilyValueHeating

Guest favourite
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, 146 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!

FamilyValueNearby

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, 133 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

ValueLocationAccess

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.
Guesthouse in Longwood
4.98 out of 5 average rating, 137 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.

FamilyValueSolo travel

Guest favourite
An open-concept studio features a queen bed with crisp white linens and a ceiling fan overhead. A kitchenette with white cabinetry and a dark countertop is present alongside a small dining area. A wall-mounted TV is positioned for viewing from the bed.
Home in Casselberry
5 out of 5 average rating, 27 reviews

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

LocationValueAccuracy

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!

LocationFamilyRiver

Top Guest favourite
Cottage in Winter Park
4.95 out of 5 average rating, 460 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!

LocationFamilyParking

Top Guest favourite
A hot tub is positioned beside a gazebo, with comfortable seating and decorative lighting. Lounge chairs are arranged around a spacious pool deck, surrounded by green foliage and palm trees. The evening sky is visible in the background, creating a tranquil outdoor environment.
Home in Casselberry
4.98 out of 5 average rating, 48 reviews

Wana Chill Spot *Pool *Spa *Bar *Ping Pong *BBQ

Our home brings together elements of comfort, convenience, and fun with relaxed and social vibes. Ideal for families exploring central Florida who want to avoid the crowds. Nestled in a quiet neighborhood you’ll find shopping, restaurants, groceries, parks & golf walking distance. ☀️Highlights: Pool (not heated) & Hot Tub (very hot!) Outdoor lounges Propane firepit table & grill Table tennis Eclectic bar area Grand TVs Fully equipped kitchen Small Gym with free weights

ValueLocationCheckout

Guest favourite
Home in Casselberry
4.88 out of 5 average rating, 58 reviews

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!!

FamilyLocationAmenities

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, 118 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 a sectional couch. 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.

ValueFamilyCheckout

Guest favourite
A spacious living area features contemporary furnishings, including a black leather sofa and an accent chair in yellow. A large TV is mounted above a stone fireplace, and natural light enters through large windows. A stylish rug enhances the overall ambiance.
Home in Casselberry
4.88 out of 5 average rating, 16 reviews

Moxy Luxe House / Heated pool/ King Bed ste

Welcome to your new home away from home! This stunning single-level property boasts an open floor plan that is perfect for relaxing with the family. The cheerful modern decor is sure to brighten your day, and the property is equipped with everything you need for a comfortable stay, including a washer and dryer, and TVs in all bedrooms. This property is located in a quiet cul de sec with free parking and full fenced in yard..

FamilyLocationNearby

Popular amenities for Casselberry holiday rentals

When is the best time to visit Casselberry?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$193 AUD$187 AUD$201 AUD$180 AUD$177 AUD$168 AUD$161 AUD$173 AUD$170 AUD$173 AUD$187 AUD$194 AUD
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 $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!

  1. Airbnb
  2. United States
  3. Florida
  4. Seminole County
  5. Casselberry