
Vacation rentals with a pool in Casselberry
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Casselberry
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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!😊

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.

Comfortable Guest Suite-Stylish Altamonte Springs!
Enjoy a stylish experience with *remodeled pool* in this Altamonte Springs Florida guest suite. This luxury 830 sq ft unit offers a living room, kitchenette, bedroom, bathroom and large pool in the peaceful Spring Valley Farms residential community. It is located 8 miles north of downtown Orlando, a primo location close to downtown, both ocean coasts, Wakiwa Springs State Park, theme parks (Disney, Universal, SeaWorld, more), Crane's Roost, and many other great destinations in central Florida!

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!

"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.

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

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.

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

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!

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.

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.

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.
Popular amenities for Casselberry rentals with a pool
House rentals with a pool

3 BR/2BA Home w Private Pool~12 min to Airport!

Lake Dora Dream-Waterfront/Pool

Lakefront 4 Bed 3 Bath Private Home Free Spa Heat

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

Private pool home near Downtown

Rate Discount~ Pool~Private Country Retreat

2-bedroom home with pool near Kings Landings!

BBQ Grill | Wi-Fi | Pool Access | 20 Min Disney
Condo rentals with a pool

Luxury Condo On I-Drive & One Mile from Universal

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Location,Location 3bd 2bth near parks conv.ct/Int.

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT

Amazing Pet-Friendly 3BR condo near Epic Universe!

Lakefront Resort Condo near Disney and Universal

IS1-107 - Orlando Condo Near Disney | 2BR

3171-206 Resort Lake View Disney Universal Orlando
Other vacation rentals with a pool

Livingston Pool House- In The Heart of Downtown

Moxy Luxe House / Heated pool/ King Bed ste

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Kyle's Place - Private Unit, Pool + Laundry Room

Wana Chill Spot *Pool *Spa *Bar *Ping Pong *BBQ

Joe's Bar and Grill

Luxury Villa: Heated Pool, Gym & Epic Universe

Lakefront House ~ Pool ~ 5 Star Location
When is the best time to visit Casselberry?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ426 | ﺩ.ﺇ551 | ﺩ.ﺇ562 | ﺩ.ﺇ551 | ﺩ.ﺇ555 | ﺩ.ﺇ679 | ﺩ.ﺇ621 | ﺩ.ﺇ632 | ﺩ.ﺇ639 | ﺩ.ﺇ646 | ﺩ.ﺇ705 | ﺩ.ﺇ735 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about vacation rentals with a pool in Casselberry

Total vacation rentals
Explore 60 vacation rentals in Casselberry

Nightly prices starting at
Casselberry vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 2,270 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Casselberry vacation rentals include wi-fi 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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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Daytona Beach Bandshell
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Daytona International Speedway
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Playalinda Beach
- Give Kids the World Village
- Disney's Hollywood Studios




