Holiday houses in Casselberry

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Top-rated holiday rentals in Casselberry

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Guest favourite
An open living area features a modern kitchen equipped with stainless steel appliances, including a microwave and refrigerator. A comfortable green sofa with throw pillows faces a wall-mounted television. A glass coffee table is surrounded by four chairs, enhancing the inviting communal space.
Home in Winter Park
4.89 out of 5 average rating, 101 reviews

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.

Guest favourite
A spacious pool house is visible behind a lush, green lawn, surrounded by trees. A paved path leads to the inviting pool area, while a gated fence provides added privacy. Sunlight filters through the leaves, creating dappled patterns on the grass.
Bungalow in Fern Park
4.87 out of 5 average rating, 602 reviews

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.

Top Guest favourite
A comfortable sitting area is visible, featuring a blue sofa with yellow accent pillows, a gray armchair, and a dark wood TV stand with a large flat-screen TV. Natural light filters through the large windows adorned with blinds, creating a bright and inviting space.
Guest suite in Altamonte Springs
4.97 out of 5 average rating, 115 reviews

Private Studio King Bed & Massage Chair + Sofa

Quiet, peaceful & centrally-located private studio in Altamonte Springs. 1st floor, 2 private entrances, full kitchen, private AC, strong WiFi, free parking, and total privacy. Walk to Sandlando Park & Seminole Wekiva Trail. Just 2 blocks from I-4, 1.5 mi to Cranes Roost, Uptown & Altamonte Mall. Less than 10 min to Downtown Orlando, Wekiva Springs, hospitals & shopping. Ideal for remote work, extended stays, couples or solo travelers. Enjoy comfort, location & convenience. Book now and enjoy!

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
4.89 out of 5 average rating, 131 reviews

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!

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, 129 reviews

"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.

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, 125 reviews

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

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, 110 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.

Superhost
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
4.85 out of 5 average rating, 108 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
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, 21 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

Guest favourite
An open living area includes a modern kitchen with white cabinetry and stainless steel appliances alongside a spacious seating area. A black sectional sofa faces a large window, allowing natural light to brighten the space. Decorative plants are arranged on a nearby shelf.
Home in Altamonte Springs
4.97 out of 5 average rating, 225 reviews

3/1 house conveniently located in central Florida!

Relax with your whole family in this peaceful quiet home. Your home away from home is Conveniently Located close to all the attraction and beaches. It's a small 800 sq ft 3 bed 1 bath House with Casper beds and flat screen in every room. 10 Minutes away from the Altamonte Springs hospital. Full Stocked kitchen with everything you need to cook a home cooked meal. It's a perfect place to stay with your family instead of a Hotel for a more comfortable stay and peace of mind.

Top Guest favourite
A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.
Treehouse in St. Cloud
4.97 out of 5 average rating, 1,094 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Guest favourite
A modern kitchen is seen, featuring white cabinetry and a speckled granite countertop. Stainless steel appliances, including a microwave and toaster, are positioned conveniently. A small potted plant adds a touch of greenery, while natural light filters in through the window above the sink.
Condo in Winter Park
4.84 out of 5 average rating, 114 reviews

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

When is the best time to visit Casselberry?

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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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