Holiday rentals in Casselberry

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Top-rated holiday rentals in Casselberry

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Guest favourite
The inviting pool area is framed by a wooden deck, featuring two lounge chairs and a large umbrella for shade. The clear water reflects the blue sky and surrounding greenery, creating a serene atmosphere for relaxation.
Home in Altamonte Springs
4.94 out of 5 average rating, 106 reviews

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!😊

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 Maitland
4.87 out of 5 average rating, 610 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
4.98 out of 5 average rating, 124 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!

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
4.87 out of 5 average rating, 140 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!

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, 133 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.

Superhost
A single-story suburban home is pictured, featuring a neatly manicured lawn and a large driveway. The entrance is flanked by a decorative gray wall and a two-car garage. The roof is covered with light shingles, set against a clear blue sky and surrounding greenery.
Home in Fern Park
4.81 out of 5 average rating, 108 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.

Guest favourite
A modern living space is highlighted by a plush grey sofa and mid-century styled furniture. A large window invites natural light, showcasing views of the outdoors. Decorative elements, including a small plant and artwork, add character to the room while maintaining a clean aesthetic.
Loft in Orlando
4.92 out of 5 average rating, 671 reviews

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.

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, 131 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
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, 165 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 features a modern sectional sofa arranged facing a stone fireplace. Large glass doors provide natural light and views of the outdoor space. Decorative plants and a wall-mounted mirror add elegance to the cozy atmosphere.
Home in Maitland
4.85 out of 5 average rating, 154 reviews

Bonheur Ala Maison

Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

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
4.9 out of 5 average rating, 115 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.

Top guest favourite
Cottage in Winter Park
4.94 out of 5 average rating, 452 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£93£88£84£90£89£90£98£102
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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