
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.

Comfortable Guest Suite-Stylish Altamonte Springs!
Enjoy a stylish experience with *remodelled 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!

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.

Cozy Cottage in College Park.
Whether you're coming to Orlando for adventure at one of the theme parks, or a little R&R, the Cozy Cottage is the perfect place. It's charming, quiet and nestled in our back garden with a stock tank pool in College Park, in The city of Orlando. Winter Park, Rollins college, lou gardens, Orlando Science Center, Advent Heath, Orlando health, Dr. Phillips center, Ivanhoe, lake eola, camping world stadium and the Kia center, are all in the immediate area. UCF, Full Sail and Florida Central too.

St.John suite
Luxurious space with PRIVATE ENTRANCE, BATHROOM, and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree lined streets, Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting.

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.

"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. Luxury and 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 and accessible for all attractions in Central Orlando. Airport is 25 minutes. SAFE NEIGHBORHOOD

Lake Front Suite -Close to all Attractions
Multi Room Suite on Little Bear Lake - Fun place to stay! The suite is attached to main house but has private entrance. 1/2 bath in Master BR. A Separate Full Luxury Bath w High Flow Therapy Shower provides Spa quality relief from a tough day! Master has King and hideabed, smart tv w Hulu. HEPA air filtrate removes viruses. Wireless internet. Kitchenette has tv, microwave, hot water kettle, coffee pot, toaster oven, charcoal grill (outside), frig/freezer w water, tea, wine & snacks.

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!

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.

Lovely Winter Park Home close to Hospitals !
Lovely Condo close to Full Sail, Rollins College, Valencia College, UCF and Advent Health Winter Park Hospital. Close to Park Avenue - Winter Park’s shopping, dining and cultural gem – boasts more than 140 boutiques, sidewalk cafes, and museums, all in the shadow of oak-canopied Central Park. In addition to the shops, dining and cultural offerings, you can plan a trip around special events that include seasonal art shows, concerts and fashion events.

Tiny Tropical House! 🏝
Welcome to life on Tropical ! Our tiny home is located right outside of Oviedo. About 20 mins away from UCF and an hour from Cocoa and most major theme Parks. We live down the street from Lake Mills Park which is a beautiful park with a great lake you are welcome to use our water crafts too! *Please note that the ladder to access the loft above the restroom is not secured to the wall and is moveable. If you proceed to book use at your own risk.
Popular amenities for Casselberry rentals with a pool
House rentals with a pool

The Cypress House

Charming Retreat In Winter Park

Gated community XL pool Home 2500sq/f

Private Pool at Flamingo Cottage

Markham Woods 4BR Pool Retreat near Attractions

Tropical Oasis - Heated Luxury Pool - Game Room

3,000 Sqft Historic Home With Pool Near Everything

Spacious Home with Pool & Hot Tub near Downtown
Condo rentals with a pool

Luxury Condo On I-Drive & One Mile from Universal

5 mins Universal 10 mins Epic park | Rustic LOFT

ORLANDO SUITE@ UNIVERSAL/DISNEY/CONVENTION CENTER

Maria Luz Studio-Huge Terrace/Universal area.

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Modern Lake view Condo 1 mile from Disney

Luxurious Spot 10 Mins Away to Most Attractions!!!

Studio close to Universal & Epic + free Netflix
Home rentals with a private pool

Wr001or (1stfororlando)

630sst- the Retreat at Championsgate

Disney's Championsgate: Private Pool & Arcade Fun!

Beautiful 9 Br Pool Home In the Solterra Resort!

Luxury Home 7 Bedrooms Near Disney!

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

Champions Gate
When is the best time to visit Casselberry?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$24,258 GYD | G$31,368 GYD | G$31,995 GYD | G$31,368 GYD | G$31,577 GYD | G$38,687 GYD | G$35,341 GYD | G$35,968 GYD | G$36,386 GYD | G$27,603 GYD | G$26,558 GYD | G$28,440 GYD |
| 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 G$6,274 GYD per night before taxes and fees

Verified guest reviews
Over 2,160 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

4.8 Average rating
Casselberry stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with pools Seminole County
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- Rentals with pools United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Walt Disney World Resort Golf
- Daytona International Speedway
- Playalinda Beach
- Aquatica
- Apollo Beach
- Titusville Beach
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club




