
Holiday houses in Casselberry
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Top-rated holiday rentals in Casselberry
Guests agree: these stays are highly rated for location, cleanliness and more.

Orlando Poolside Oasis
Welcome to the Orlando Poolside Oasis!! This property is located in a quiet suburb of Orlando, with easy access to both theme parks and the beaches. This 3 bedroom 2 bathroom pool home will allow you to vacation in comfort and style. We have recently completed many upgrades to the property, including a newly renovated kitchen and bathrooms. We hope you love this property as much as we do! The home is also very baby friendly (crib upon request, stroller, baby bath,etc)!We can’t wait to host you!😊

Unique Concrete House Boat! No cleaning fees!
This ferrocement boat Later Gator was made in Sweden in 1973. That’s right! It’s made of concrete! The boat circumnavigated the globe twice before eventually ending up here in sunny Sanford FL. We spent 2 years completely renovating everything and tried to leave as much of the boat’s original personality intact while adding modern amenities. Restaurant/bar, pool, laundry facilities, showers and restrooms, diner, and marina store all on site, and downtown historic Sanford and river walk close by.

Treehouse at Danville
Private Getaway seen on Netflix' Most Amazing Vacation Rentals! Fulfill your dream of staying in a tree house! For safety reasons, this venue is for adults only. We do not allow children or pets. The Treehouse has a tree trunk elevator, private shower, air-conditioning, and real toilet inside so that you can bring your significant other(no compost toilet here). This 18 foot yurt has accent lighting to create the mood of living in the trees on a starry night. Danville is a glamping experience.

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.

NEW 1BRM Guesthouse | King Bed | Central Florida
Nestled in a private and central location, this newly constructed space offers everything needed for a relaxing stay. The space is perfect for up to four guests, featuring a king size bed, full kitchen, and smart TVs in every room. Enjoy the convenience of high-speed Wi-Fi, a spacious shower, washer / dryer, and a private driveway. Located close to Downtown, Theme Parks, the Stadiums, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for your short term or long term stay.

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!

"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.

Contemporary Loft Near Downtown
Conveniently located between the foodie-friendly Milk District and Downtown Orlando, this impeccably thought-out space features a spacious loft style open floor plan perfect for a couple or small group. The floor to ceiling windows allow natural light to fill the space while providing complete privacy during your stay. Upscale Winter Park restaurants and the vibrant Thornton Park art scene are only a short drive away. Universal is only 20 minutes away, Disney is 35 minutes, MCO 20 minutes.

UPSCALE LOFT SPACE CLOSE TO DOWNTOWN.
Tucked right between the charm of Lake Eola Park and the eclectic, foodie-loved Milk District, this one-of-a-kind space puts you in the heart of Orlando’s most vibrant neighborhoods. Step inside to an airy, open floor plan highlighted by floor-to-ceiling windows that flood the space with natural light. When you’re ready to venture out, you’re just minutes from the upscale dining and shopping of Winter Park, as well as the walkable streets, art galleries, and lively energy of Thornton Park.

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

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

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.
Popular amenities for Casselberry holiday rentals
Other great holiday rentals in Casselberry

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

The Tiny Cottage in the Springs/ Central FL

Spacious Modern Japandi Retreat - Winter Park

Spaciious Countryside Home In Sanford | 3BR, 2.5BA

The Briarcliff

scape to sunny Florida.

Pool, Hot Tub, Massage Chair, Golf, & Music Vibes!

Home away from home in Orlando!
When is the best time to visit Casselberry?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $196 NZD | $232 NZD | $230 NZD | $213 NZD | $210 NZD | $200 NZD | $191 NZD | $205 NZD | $201 NZD | $205 NZD | $222 NZD | $230 NZD |
| 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 vacation rentals in Casselberry?
Casselberry has more than 80 family-friendly stays. 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 vacation rentals in Casselberry?
Four-legged friends are welcome in Casselberry. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Casselberry?
Yes! Work meets play with ease at over 80 vacation rentals in Casselberry featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Casselberry house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 house rentals with pools in Casselberry, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Casselberry have air conditioning?
Absolutely! We offer over 100 house rentals with air conditioning in Casselberry. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Casselberry have a kitchen?
Absolutely! We offer over 10 apartment 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 apartment rentals in Casselberry have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Casselberry. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Casselberry?
Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with a kitchen, over 100 homes with wifi, over 100 homes with free parking, over 100 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 140 holiday rentals in Casselberry

Nightly prices starting at
Casselberry holiday rentals start at $34 NZD 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!
Destinations to explore
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- Rentals with a fireplace Casselberry
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- Family-friendly rentals Casselberry
- Pet-friendly rentals Casselberry
- Rentals with a fire pit Casselberry
- Rentals with a patio Casselberry
- Fitness-friendly rentals Casselberry
- Rentals with pools Casselberry
- House rentals Casselberry
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- Apartment rentals Casselberry
- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Orange County Convention Center
- Walt Disney World Resort Golf
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
- Universal's Volcano Bay
- Ocean Center
- Orlando / Kissimmee KOA
- Discovery Cove
- Daytona Beach Bandshell
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Daytona International Speedway
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- Playalinda Beach




