Holiday rentals in Casselberry

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Top-rated holiday rentals in Casselberry

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

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Superhost
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
4.92 out of 5 average rating, 265 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.

Guest favourite
Home in Altamonte Springs
4.94 out of 5 average rating, 108 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!😊

Top guest favourite
Two wooden chairs with green and beige cushions are positioned beside a tranquil lake. A small table holds a bottle of wine and two glasses, framed by lush trees and a clear blue sky, creating an inviting lakeside setting.
Cottage in Sanford
4.98 out of 5 average rating, 251 reviews

Lakefront,Sanford airport, Boombah, Venue 1902,UCF

The lake front cottage is located on a private estate 1 mile south of Sanford airport, 4 miles to Sanford historic district, and 3 miles from Boombha Sports Complex. This cottage has a Fully equipped kitchen, light bright liv/din area, screened wrap around porch. Perfect spot for your next family vacation or weekend get away. While staying at the cottage you are welcome to enjoy our paddle boards and kayaks. Also catch and release fishing. No pets. Discounts for non-refundable cancellations.

Top guest favourite
The exterior of the home features a welcoming front entrance with a gray door and arched window. The pathway is lined with colorful foliage, and tropical plants surround the entrance. A lamp post stands at the forefront, providing soft illumination amidst the lush greenery.
Home in Sanford
4.98 out of 5 average rating, 285 reviews

Clean, cozy home in a GREAT location

This clean, comfortable home is in a peaceful neighborhood and centrally located to everything you may wish to enjoy while on your Central Florida vacation. Literally two to three minutes away from I-4, highway 417 and a multitude of shopping and dining options. Universal Studios, Sea World and Daytona International Speedway are all within about 40 minutes, while Disney World and Kennedy Space Center are about 50 - 60 minutes. Also easy access to Sanford and Orlando International Airports.

Superhost
A spacious living area features a comfortable sectional couch and an accent chair, with a wooden coffee table at the center. A 65” SMART TV is mounted on the wall across from the seating. Natural light enters through a window, and a sliding barn door leads to the bathroom.
Home in Casselberry
4.87 out of 5 average rating, 143 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 serene pool is surrounded by lush greenery, featuring a stone patio. Two white lounge chairs are positioned under a large umbrella, providing shade. The scene is set against a clear blue sky with a few fluffy clouds, enhancing the peaceful ambiance.
Guest house in Longwood
4.98 out of 5 average rating, 135 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 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 Colonialtown South
4.92 out of 5 average rating, 674 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.

Top guest favourite
A crystal-clear pool reflects the sunlight, with a spacious pergola providing shade nearby. Comfortable lounge chairs are positioned around the pool, creating a relaxing outdoor space surrounded by greenery.
Home in Casselberry
4.93 out of 5 average rating, 132 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
A screened-in pool area features clear blue water with a natural stone accent. Surrounding plants, including tall green palms, add a touch of greenery. The tranquil atmosphere is enhanced by decorative elements such as a stone lantern and potted plants.
Home in Longwood
4.97 out of 5 average rating, 120 reviews

Relaxing 3-Bedroom Pool Getaway

This is a 3-bedroom 2-bath home, bathroom in the main bedroom connects directly to the pool. Accommodates comfortably up to 6 people. We have a wide range of amenities including wifi, TV, covered pool, fully equipped kitchen, and more! This is located in a quiet neighborhood located 30 minutes from Universal Studios, Sea World, and Disney World. The home comes with pool toys, board games, a space for an outdoor bar! The outdoor space is enclosed to keep out mosquitos and other pests.

Top guest favourite
A tranquil pool area is surrounded by a screened enclosure, showcasing a crystal-clear saltwater pool. Comfortable lounge chairs are positioned near the water, and lush greenery, including ferns and tropical plants, enhances the serene setting.
Guest suite in Lake Mary
4.96 out of 5 average rating, 388 reviews

Stylish & spa like Getaway - peaceful garden suite

Relax and unwind from your busy life in this serene and quiet getaway. We are located 5 minutes to shopping and dining in downtown Lake Mary in a beautiful and safe neighborhood. Enjoy the solar heated saltwater pool and the comfy outdoor lounge area, Enjoy the backyard with its mature trees and tropical flowers. The indoors come with a luxury and modern wellness bathroom. Soak in the oversized jetted tub or reenergize in the stylish rainfall shower with inbuilt bench and mood lighting.

Top guest favourite
Guest house in Orwin Manor
4.99 out of 5 average rating, 123 reviews

Location, Location, Location!

Enjoy a stylish experience at this centrally-located Guest House. It is located in an excellent area close to the downtown Orlando, excellent restaurants, and much more. It is fully furnished and equipped with new appliances (washer and dryer included) and furniture. It is located minutes from Winter Park, Downtown Orlando and theme parks. Downtown Orlando 3 miles (6 min) Advent Health Hospital 0.6 miles (2 min) Walt Disney World 20 miles (23 min) Universal Studios 11 miles (18 min)

Guest favourite
The exterior of the property features a well-maintained lawn with manicured shrubs and trees. A spacious driveway leads to a two-car garage, and the entrance is framed by a covered porch, highlighting the welcoming entrance to the suite.
Guest suite in Casselberry
4.91 out of 5 average rating, 116 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.

Popular amenities for Casselberry holiday rentals

When is the best time to visit Casselberry?

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Avg. price£101£98£105£94£92£88£84£90£89£90£98£101
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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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  5. Casselberry