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Family-friendly vacation rentals in Casselberry

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Quick stats about vacation rentals that are family-friendly in Casselberry

  • Total vacation rentals

    Explore 80 vacation rentals in Casselberry

  • Nightly prices starting at

    Casselberry vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,930 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Casselberry vacation 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!

Top-rated family-friendly rentals in Casselberry

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
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

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!😊

4.95 out of 5 average rating, 112 reviews
Guest favorite
A spacious bedroom features two sets of twin bunk beds, accommodating multiple guests. A cozy seating area with a chair and ottoman is positioned in front of a mounted TV. Large windows invite natural light, enhancing the bright, modern decor.
Home in Casselberry

Sept. Specials, welcome the fall. Long term ok

Remodeled, modern and spacious 3-bedroom home in the Orlando area. Perfect for a weekend trip to the parks or a family vacation! ✨Fully Remodeled ✨Modern Design ✨Fully Stocked Kitchen ✨Close to Wekiva Springs ✨Private Fire Pit Area ✨Short Drive to the Beach ✨Short Drive to Disney World and Universal Studios! ✨Close to Orlando Airport ✨Reliable High Speed Wifi ✨Smart TV's ✨Outdoor Grill ✨Patio ✨Easy Freeway Access ✨Quiet Neighborhood ✨Insurance Displacement Stays Welcome ✨Long Term Stays Welcome

4.91 out of 5 average rating, 100 reviews
Guest favorite
A well-lit bedroom features a spacious bed dressed in a light blue coverlet. A nightstand with a lamp is located beside the bed. An closet with sliding doors is visible, providing additional storage. Neutral-toned walls and tiled flooring contribute to a serene ambiance.
Guest suite in Casselberry

Comfortable and quiet place

Forget your worries in this spacious and serene space, we offer our guests k cups coffee(Victor Allens), sweteners (splenda) and "Oasis Bliss" personal care amenities( shampoo,conditioner, body lotion, bar soap).Private kitchen and bathroom. Also located less than an hour to Disney and Universal parks. Many restaurants and shoping centers around the area, 15 miles- 20 mins to "Orlando Sandford International Airport". Feel free to ask questions and our family will be in contact with you, thanks

4.85 out of 5 average rating, 102 reviews
Top guest favorite
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

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.

4.98 out of 5 average rating, 295 reviews
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

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.

4.82 out of 5 average rating, 122 reviews
Guest favorite
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

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

4.93 out of 5 average rating, 137 reviews
Top guest favorite
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

"Winnie's Place" A Peaceful Guesthouse with Pool.

Share the quiet yard and pool with hosts. 1 hr. from Disney & the beaches. 12 yr & older only. Single Sofa bed for 3rd guest. NOT a heated pool. Not Handicap Certified, but most wheelchair guests have not had issues. Narrowest opening 32" Ramp into unit by pool. Shower no steps. Queen bed height 29"-standard cabinets. Grab bars in bathroom. Airbnb's Accessibility Policy has exempted this listing from accepting Service & Emotional Support Animals due to owner's severe health condition.

4.98 out of 5 average rating, 142 reviews
Top guest favorite
A charming lakefront cottage is viewed from across the water, showcasing its blue exterior. The porch area includes a deck with seating, and two light-colored lounge chairs are positioned on the grassy lawn, surrounded by lush greenery and trees.
Cottage in Altamonte Springs

Charming Private Lakefront Cottage Retreat

You can fully relax in this adorable lakefront cottage. We're sure you'll enjoy all of the wonderful amenities this peaceful property has to offer. Our incredibly unique cottage is nestled under a large grand oak tree and tucked away behind climbing jasmine vine clad fencing and security gates. Inside, you will find a new remodeled fully stocked kitchen and luxury bathroom. Our cozy cottage has all the comforts of home and more. Reserve your stay today and enjoy this special property.

4.99 out of 5 average rating, 155 reviews
Top guest favorite
A screened-in pool area features a clear blue pool surrounded by landscaped greenery. A stone waterfall adds a natural touch, complemented by decorative plants and a Zen-inspired statue. Sunlight filters through the trees, enhancing the tranquil ambiance.
Home in Longwood

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.

4.97 out of 5 average rating, 132 reviews
Top guest favorite
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

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

4.95 out of 5 average rating, 175 reviews
Superhost
A backyard swimming pool is surrounded by a natural landscape, featuring colorful floaties resting on the water's surface. Comfortable seating is arranged nearby, and palm trees provide a tropical touch to the serene outdoor setting, all under a softly lit evening sky.
Home in Altamonte Springs

Private Pool / Cozy Central Florida Home

Updated four-bedroom home in Altamonte Springs, ready for your stay! Perfect for groups. Plenty of free parking in the driveway and curb side. Only minutes from I-4, which means easy access to your favorite spots in and around Central Florida. Universal Studios, for example, is about 25 minutes away. SeaWorld is 30 and Disney Springs is about 35, depending on traffic. Plenty of sports complexes are nearby. Uptown Altamonte is just around the corner. No parties or events please.

4.86 out of 5 average rating, 139 reviews
Top guest favorite
The screened-in pool area features a tranquil pool with a soft blue hue, surrounded by white decking. A small table holds a lit lantern beside two lounge chairs, providing a serene space for relaxation under the evening sky.
Home in Maitland

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.

4.98 out of 5 average rating, 130 reviews

Popular amenities for Casselberry family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
The pool area is enclosed with a protective screen, featuring a spacious heated pool surrounded by a wooden deck. A green umbrella provides shade over a small table and chairs, while a bright yellow building is visible in the background.
Home in Altamonte Springs

Tropical Pool/Spa Home-Disney-Theme Parks-Beaches

4.98 out of 5 average rating, 117 reviews
Top guest favorite
A spacious living area is highlighted by a sleek, modern design featuring polished floors. A green couch and two accent chairs are arranged around a wooden coffee table. A dining table with ample seating is situated nearby, complemented by decorative wall art and soft lighting.
Guesthouse in Orlando

Luxe Guest House| Pool, HotTub| UCF, Rollins

4.99 out of 5 average rating, 209 reviews
Superhost
Home in Maitland

The Bird House Spa Winter Park

4.91 out of 5 average rating, 104 reviews
Top guest favorite
A heated pool surrounded by lush greenery features a stone ledge and a small waterfall. Hammocks are placed for relaxation. The screened patio allows for unobstructed views of the sunset, creating a tranquil setting. Warm lighting highlights the natural textures of the landscape.
Home in Orlando

Spacious Home with Pool & Hot Tub near Downtown

4.96 out of 5 average rating, 172 reviews
Guest favorite
Two red kayaks are positioned on a tree trunk beside a peaceful lake, reflecting blue skies and lush greenery. A covered patio area is visible, alongside a hot tub, creating an inviting space for relaxation by the water.
Home in Lake Mary

Independent Unique Lake guest house/kayaks/jacuzzy

4.85 out of 5 average rating, 372 reviews
Guest favorite
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

Bonheur Ala Maison

4.85 out of 5 average rating, 167 reviews
Guest favorite
An outdoor area features a pool surrounded by lounge chairs and a sleek design. Soft lighting illuminates the space, creating a cozy ambiance. A sauna is visible, with a comfortable lounge area nearby, and a large screen mounted for entertainment.
Home in Longwood

Recharge @ Timberland Lodge: Pool Hottub Sauna

4.89 out of 5 average rating, 109 reviews
Guest favorite
An outdoor space features a heated pool and a hot tub, surrounded by stone masonry. A custom bar, crafted from wood, is visible alongside tropical plants. Two built-in TVs are fitted above the bar area, enhancing the outdoor living experience.
Home in Orlando

Stunning Orlando Getaway w/Spa & Heated Pool

4.92 out of 5 average rating, 178 reviews

Family- and pet-friendly home rentals

Top guest favorite
The spacious kitchen features a large island with a granite countertop, white cabinetry, and modern appliances. A comfortable seating area with two couches is visible in the background, complemented by wood flooring that enhances the home’s open layout.
Home in Lake Mary

RemodeledHouse w/king beds near Downtown Lake Mary

4.86 out of 5 average rating, 252 reviews
Guest favorite
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

Renovated Peaceful Luxury Walk to Mall Park Publix

4.87 out of 5 average rating, 127 reviews
Superhost
A modern living room is presented, featuring a deep blue sectional sofa and a coordinating armchair. A circular glass coffee table sits at the center, complemented by a decorative vase with flowers. Natural light enters through a large window, enriching the neutral tones of the space.
Home in Altamonte Springs

Elegant, Spacious Three Bedroom Residential House.

4.86 out of 5 average rating, 222 reviews
Guest favorite
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

Lovely Winter Park Home close to Hospitals !

4.83 out of 5 average rating, 127 reviews
Top guest favorite
A spacious living area is highlighted by exposed wooden beams above. A light-colored sofa is complemented by two bright orange chairs. A round coffee table is centered on a textured rug, while large windows provide natural light and views of the outdoors.
Home in Altamonte Springs

A Home Where Eclectic Luxury Meets Affordability

4.98 out of 5 average rating, 364 reviews
Guest favorite
A comfortable seating area features a soft blue chaise lounge beside a side table with a lamp. A large mirror leans against the wall, reflecting natural light from a nearby window. Framed artwork adorns the walls, enhancing the space's aesthetic.
Guest suite in Altamonte Springs

Abe and su villa

4.86 out of 5 average rating, 114 reviews
Top guest favorite
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

Cozy King Studio • Massage Chair • Sleeps 4

4.97 out of 5 average rating, 143 reviews
Top guest favorite
A serene pool area is featured, reflecting the clear blue sky and surrounding greenery. The pool is bordered by a tiled edge, with colorful plant life adding vibrancy. A covered patio with a picnic table sits in the background, offering a shaded relaxation area.
Home in Orlando

Modern Tropical House Heated Salt Pool

4.92 out of 5 average rating, 180 reviews

Family-friendly home rentals with a pool

Guest favorite
A spacious living room features a large sectional couch adorned with patterned cushions. A dark wooden coffee table sits at the center atop a neutral area rug. Natural light filters through the windows, reflecting off the light tile flooring and illuminating the room.
Home in Winter Park

Cozy Winter Park Cottage

4.96 out of 5 average rating, 107 reviews
Top guest favorite
A spacious living room is featured with light-colored tile flooring. A large flat-screen television is mounted on the wall above a dark media console. One side includes a sleek sofa and a foldable futon, while a round coffee table is situated in the center.
Guest suite in Altamonte Springs

Comfortable Guest Suite-Stylish Altamonte Springs!

4.94 out of 5 average rating, 203 reviews
Guest favorite
A welcoming living area features comfortable seating arrangements around a central ottoman. A large television is placed on a stylish console, with decorative plants and artwork enhancing the space. Natural light streams through windows, contributing to a bright, inviting environment.
Home in Sanford

The Cypress House

4.97 out of 5 average rating, 183 reviews
Guest favorite
Home in Sanford

Private Pool at Flamingo Cottage

4.87 out of 5 average rating, 284 reviews
Guest favorite
Home in Orlando

Last Minute Deals End Soon, Orlando Home Pool Dock

4.97 out of 5 average rating, 120 reviews
Top guest favorite
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

Maitland-Orlando Area, FL. Pool House Bungalow

4.88 out of 5 average rating, 631 reviews
Top guest favorite
The exterior of a three-bedroom home displays a welcoming entrance with a paved walkway leading to a covered porch. Lush greenery and flowering plants line the front yard, complemented by a white railing. The structure is topped with a metal roof and features large windows.
Farm stay in Apopka

Farmhouse near the Springs

4.95 out of 5 average rating, 149 reviews
Top guest favorite
A serene pool area features a clear blue pool surrounded by elegant tile flooring. Comfortable lounge chairs are arranged around the pool, providing ample space for relaxation. Potted plants add a touch of greenery to the setting, contributing to a calming atmosphere.
Guest suite in Altamonte Springs

St. Augustine suite

4.96 out of 5 average rating, 395 reviews

When is the best time to visit Casselberry?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,448 GYDG$40,795 GYDG$40,795 GYDG$40,586 GYDG$41,841 GYDG$39,958 GYDG$38,075 GYDG$35,983 GYDG$34,937 GYDG$36,820 GYDG$39,330 GYDG$40,795 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

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