
Holiday houses in Casselberry
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Top-rated holiday rentals in Casselberry
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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.

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 it. 📝Please note: There’s no stove; however, there is a cook-plate with two burners to cook on.

Maitland-Orlando Area, FL. Pool House Bungalow
Large open space adjacent to a beautiful pool, waterfall, and fantastic lake view. 27 miles to Disney World, close to Park Avenue, local hospitals, Universities, and less than an hour to local beaches. Only 18 miles to MCO-Orlando International Airport. Great shopping within 3 miles. Location is secluded with large trees, lakeside, and adjacent to the commuter train track. The train runs by on regular basis. Please note in the pictures the pool creates the ambiance to make your stay complete.

Cozy 4/2, King Beds, Pergola, Hot Tub & 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!

"Winnie's Place" A Peaceful Guesthouse with Pool.
Share the quiet backyard and pool with your hosts. Half was between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from Interstate-4. NOT a heated pool. Wheelchairs are fine. Driveway Entry gate 39"- Breezeway to Ramp entrance 32"- Slider Entrance 33"-Bedroom door 35"-Shower (no step) 35"-Laundry 32"-Closet 35"-Queen bed 29"-standard cabinets. We are not Handicap Certified but most wheelchair guests have not had issues. Grab bars are in the bathroom.

Villa with Guest House & Pool-Patio
Welcome to this Amazing House Pool-Patio with 4 Bedrooms + 2 Bathrooms and optional guest house. Luxury and 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 and accessible for all attractions in Central Orlando. Airport is 25 minutes. SAFE NEIGHBORHOOD

Cozy 2/2 Home - Downtown Winterpark/Orlando
You will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, 5 minutes from Advent Health Hospital, you will be 5 minutes from Downtown Orlando an, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! Dubsdread golf course within walking distance! Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music

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.

Florida Poolside Paradise a Great Place to Unwind!
Welcome to our exquisite 4-bedroom vacation rental in the heart of Maitland, Florida – a true gem where luxury meets convenience. This upscale home boasts fine furnishings and a private pool, making it the ideal retreat for families or groups seeking both comfort and style during their Sunshine State getaway. The house is located in a residential neighborhood with plenty of restaurants and shopping within a 5 minute drive. Convenient location off Rt 436. and half hour to the airport.

Sunset Cottage in Lake Mary, Florida
Located on beautiful Lake Mary, this completely renovated studio sized guest house offers beautiful sunsets over the lake from a private patio. A comfortable queen bed, stylish sitting area and fully stocked kitchenette make for a wonderful stay in the Lake Mary- Sanford area. Minutes from the Sanford airport, close to the Sunrail station and 45 minutes to either Disney World or the beach. Our guest cottage is a perfect place to visit. Please note: The cottage is lakeview only.

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!

Lovely Winter Park Home close to Hospitals !
Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.
Popular amenities for Casselberry holiday rentals
Other great holiday rentals in Casselberry

10 min to Winter Park, Games, Gym, King bd, Coffee

Serene private home near the fun

Modern Townhouse Retreat | Sanford Getaway w/ Pool

The Winter Park Experience

scape to sunny Florida.

Spacious 4 bedroom single story home

Cozy Winter Park Retreat

Charming Winter Park 3 Bedroom Villa with Pool
When is the best time to visit Casselberry?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $164 AUD | $194 AUD | $192 AUD | $178 AUD | $175 AUD | $167 AUD | $160 AUD | $171 AUD | $168 AUD | $171 AUD | $185 AUD | $192 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
Are there family-friendly house rentals in Casselberry?
Casselberry has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Casselberry?
Experience the best of Casselberry with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly house rentals in Casselberry?
Four-legged friends are welcome in Casselberry. Choose from more than 40 house rentals for guests traveling with pets.
Are there house rentals with a dedicated workspace in Casselberry?
Yes! Work meets play with ease at over 60 house rentals in Casselberry featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Casselberry vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Casselberry, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Casselberry have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Casselberry. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Casselberry have a kitchen?
Absolutely! We offer over 90 house rentals with a kitchen in Casselberry. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Casselberry have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Casselberry. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Casselberry have free parking?
Absolutely! We offer over 100 house rentals with free parking in Casselberry. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Casselberry?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Casselberry

Total holiday rentals
Explore 150 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 4,620 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 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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- Rentals with a patio Casselberry
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- Family-friendly rentals Casselberry
- Rentals with pools Casselberry
- Rentals with lake access Casselberry
- Apartment rentals Casselberry
- Fitness-friendly rentals Casselberry
- Rentals with a fire pit Casselberry
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- Pet-friendly rentals Casselberry
- House rentals Casselberry
- Rentals with a washing machine and dryer Casselberry
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Give Kids the World Village
- Epcot
- Disney's Animal Kingdom Theme Park
- Daytona International Speedway
- Kia Center
- Old Town
- Playalinda Beach
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club




