Holiday rentals with outdoor seating in Casselberry

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Top-rated rentals with outdoor seating in Casselberry

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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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
4.88 out of 5 average rating, 589 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.

Guest favourite
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
4.91 out of 5 average rating, 162 reviews

Modern Tropical House Heated Salt Pool

ā˜žSuperhost 9 years ā˜ž Large Salt Pool (W/ heated option $ Oct-April) ā˜ž3 Bedroom 3 Full Bath W/extra 4th queen daybed ā˜ž Easy access to the 417 East West express way (toll rd.) to get around Orlando ā˜žEasy smart lock self Check-in ā˜ž Driveway Parking ā˜ž Luxury bedding ā˜ž65in Smart TV with Netflix in TV room ā˜žDimmer mood lighting ā˜žIlluminated pool & landscape lighting ā˜žPool Lounge Floats ā˜žFull Kitchen ā˜žDining & Picnic table seats 6 to 8 guests ā˜žHi speed 231mb internet ā˜žUber Eats Food Delivery

Top guest favourite
A studio-style living space features a spacious bed with neutral bedding, complemented by decorative pillows. A round mirror hangs over a wooden nightstand. The kitchenette area includes a small microwave and cabinetry, while an area rug adds warmth to the wooden floor.
Guest suite in Sanford
4.98 out of 5 average rating, 244 reviews

The Secret Sanctuary in Sanford, 5min from Airport

Welcome to your quiet, spacious, and private sanctuary. Enjoy all new appliances in the full size kitchen, a 50ā€ flat screen TV, and a shaded outdoor area surrounded by greenery. It is located only minutes from the Orlando Sanford International Airport, Historic Downtown Sanford’s restaurants and shops, Lake Monroe’s scenic waterfront, and is centrally located between Florida’s beaches and the amusement parks. **Space is cleaned with EPA approved cleaners, including high touch surfaces**

Top guest favourite
A serene pool area is surrounded by lush tropical greenery, including palm trees and bamboo. A spa is integrated into the pool with a stone wall feature. Chaises with striped cushions are positioned beside the water, and a spacious patio includes various stone pavers.
Guest house in Lake Cherokee
4.97 out of 5 average rating, 117 reviews

1924 Spanish Carriage House Lower

Enjoy a shared but private compound resort in the heart of downtown Orlando! Centrally located and within walking distance to major events at the Kia Center, Dr. Phillips Performing Arts Center, restaurants, and downtown nightlife. Park on site, relax and enjoy all that this historic home has to share! Besides a fresh and clean private lodging, you'll enjoy use of the tropical pool, hot tub, gas grill, covered seating and dining area. A washer and dryer are just steps away for your use.

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, 122 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
Guest house in Sanford
4.94 out of 5 average rating, 179 reviews

Little Hidden Cottage- Near Sanford Airport

Located in Sanford FL, our Hidden Little Cottage is a private studio guest house with its own entrance, features full kitchen & bath room, queen size bed, full size pull out couch & twin size travel bed, & provides flexible self check-in. We are located 7 minutes from the Sanford Airport and Boombah Sports Complex, 10 minutes to Downtown Sanford, I –4 & 4–17. We’re also central to many Central Florida attractions such as Natural Springs, Sandy Beaches, Theme Parks and Historic Districts

Top guest favourite
A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.
Guest suite in College Park
4.97 out of 5 average rating, 242 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

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, 104 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
The spacious room features a queen bed dressed in crisp white linens, flanked by two blue accent chairs. A large area rug adds comfort underfoot. Natural light streams in through a nearby window, and a ceiling fan provides a cooling breeze. A small dining area is also visible.
Guest house in Sanford
4.93 out of 5 average rating, 123 reviews

Suite Retreat

Avoid blah hotels with high prices and stay in this luxe new apartment suite! It’s a perfect retreat in Central Florida. Located a short drive to activities, restaurants, & shops in Lake Mary or downtown Sanford - 45-55 min to Orlando theme parks or the beaches of New Smyrna. Ideal for a couple’s retreat or a getaway for one. Guests use office space designed for comfort & productivity. A cozy chair begs readers to curl up and read. The outdoor canopy hosts breakfast with birdsong!

Top guest favourite
A cozy space is illuminated by warm lighting and twinkling string lights. A comfortable bed with decorative pillows is framed by wooden accents. A small seating area features a television and has a view of the garden area with fire pit chairs, creating a relaxing outdoor ambiance.
Tiny home in Spring Lake
4.97 out of 5 average rating, 803 reviews

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

Top guest favourite
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.
Guest house in Orlando
4.99 out of 5 average rating, 172 reviews

Luxe Guesthouse w/Pool/Hot tub-Near Rollins/UCF

This luxury guesthouse (on the same property as our main house but they are completely separate) is a hidden oasis conveniently located in the middle of downtown Winter Park (Rollins College/Full Sail) and UCF. It's roughly 10 minutes to each. Close to 417 expressway (toll road) so you can easily get around to the other areas of Orlando. Note: The guesthouse is 35 minutes to Disney, 25 minutes to Universal Studios and 20 minutes to Orlando International Airport.

Top guest favourite
A spacious guest suite is presented with a queen bed and a comfortable seating area featuring a gray sofa and coffee table. A kitchenette is visible in the background, complemented by natural light from the window. Decorative elements include subtle artwork and indoor plants.
Guest suite in Altamonte Springs
4.93 out of 5 average rating, 376 reviews

The Bungalow

Welcome to your home away from home! Enter through a private driveway and enjoy the ease of keyless entry. Located across the street, Sanlando Park offers walking trails, basketball and popular tennis courts. Whether your interests are peace and quiet or adventure, you are only 30 minutes or less away from our beautiful natural springs, beaches and all major attractions. Wake up with the sunshine, put on a pot of coffee and welcome to Florida!

Popular amenities for outdoor seating rentals in Casselberry

When is the best time to visit Casselberry?

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Quick stats about holiday rentals with outdoor seating in Casselberry

  • Total holiday rentals

    Explore 50 holiday rentals in Casselberry

  • Nightly prices starting at

    Casselberry holiday rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 3,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    50 of Casselberry holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Casselberry rentals

  • 4.9 Average rating

    Casselberry stays are highly rated by guests – averaging 4.9 out of 5!

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