Vacation rentals with a pool in Casselberry

Guest suite in Altamonte Springs

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.

4.95 out of 5 average rating, 175 reviews

Comfortable Guest Suite-Stylish Altamonte Springs!

Enjoy a stylish guest experience at this centrally-located 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!

4.88 out of 5 average rating, 561 reviews

A private pool features a natural rock waterfall, surrounded by a paved patio. Lush greenery and trees provide shade, while a secure black fence encloses the area. Large windows of an adjacent building suggest inviting indoor spaces nearby, contributing to a tranquil outdoor setting.

Bungalow in Maitland

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.

Apartment in Altamonte Springs

A spacious outdoor area features a pool surrounded by a tiled patio. Comfortable lounge chairs are neatly arranged around the pool, while decorative planters with blooming flowers add a touch of color. The setting is complemented by manicured lawns and a clear sky.

4.96 out of 5 average rating, 326 reviews

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.

4.97 out of 5 average rating, 107 reviews

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 suite in Longwood

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

Share the backyard and NON Heated Pool with your hosts if we are home. Between Disney & the beaches. 12 years & older only. Sofa extends to a single bed. Minutes from I-4 makes commuting easy. 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 31". We are not Handicap Certified but most wheelchair guests do not have issues. Grab bars in the bathroom.

4.92 out of 5 average rating, 411 reviews

A private outdoor pool area is highlighted, featuring a clear blue pool surrounded by patio tiles. Comfortable lounge chairs and a dining set under large umbrellas offer shaded seating. Lush greenery forms a natural backdrop, enhancing the tranquil atmosphere.

Guest suite in Oviedo

Oviedo Oasis:2/1 attached Guest Suite;Private Pool

Cozy 2 bedroom guest suite connected to host's primary residence but has its own entrance and guests have complete privacy. There are no shared spaces inside. Living room, 2 separate bedrooms and a full size bath. Amenities include a coffee bar, mini fridge , microwave, TV, Wifi and access to non-heated swimming pool. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Universal Theme Parks: 27 miles Disney: 40 miles

4.94 out of 5 average rating, 108 reviews

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. 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

4.86 out of 5 average rating, 123 reviews

A sparkling pool is surrounded by lush greenery and palm trees, with a peaceful lounging area featuring a double canopy bed nearby. Soft blue waters reflect the clear sky, and a patio area with seating offers a comfortable space for relaxation.

Home in Maitland

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!

4.87 out of 5 average rating, 101 reviews

Home in Casselberry

Cozy 4/2, King Beds, Pergola, Hot Tub & 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 & Pool, it's great for both the adults and kiddos!

4.99 out of 5 average rating, 153 reviews

A salt-water pool is visible, featuring distinct areas with glowing blue and green lighting, set against a backdrop of a vibrant sunset sky. Surrounding the pool is a textured stone patio and a secure fence, providing a tranquil outdoor space.

Guesthouse in Orlando

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.

4.99 out of 5 average rating, 143 reviews

Home in Sanford

The Cypress House

This beautiful 2 bedroom, 1 bathroom Ranch Style home is conveniently located 3.5 miles from the Sanford International Airport and Boombah Sports Complex. The inviting landscape and backyard where you can cool off in the rustic style stock tank pool or grill out and relax on the patio. The open floor plan creates a spacious feel and every finish was selected with care. For a glamping experience check out our other listing: https://abnb.me/z3XrgOSPNFb

4.91 out of 5 average rating, 141 reviews

An aerial view of a rectangular swimming pool is surrounded by a stone patio. Lounge chairs are placed on either side of the pool, which is flanked by vibrant red bougainvillea flowers. A covered area with a sloped roof is visible in the foreground.

Apartment in Winter Park

Apt F -Modern Elegance in the Heart of Winter Park

Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two blocks to the Winter Park Village! Cozy and modern space. Pool, outdoor grill and bikes for your enjoyment. Enjoy the convenience and tranquility of one of Florida's greatest walking communities while residing in style and sophistication. The pool and grill stations are shared. Fast internet speed: 139MBPS download and 21.5 MBPS upload!

4.95 out of 5 average rating, 136 reviews

An outdoor area encompasses a screened-in pool, surrounded by lush greenery and tropical plants. A small, blue tiny home is visible next to a larger structure. Poolside seating is provided with lounge chairs and a shaded table nearby, creating a comfortable space for relaxation.

Tiny home in Chuluota

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.

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Popular amenities for Casselberry rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The in-ground swimming pool, shaped in a natural curve, is surrounded by a red deck and lush greenery. Pool toys and a basketball hoop are visible, alongside lounge chairs, providing space for relaxation and enjoyment.

4.88 out of 5 average rating, 124 reviews

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

SuzanneRating, 5 stars5 days ago

Had a nice stay with family and friends at Alyssa’s place along with 2 dogs. Was so nice to be able to bring out pets along on vacation. The house was clean, beds were comfortable, lots of space. I Spent most of my time out in the pool which was amazing.

4.87 out of 5 average rating, 241 reviews

The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.

Home in Kissimmee

3 bedroom Villa in Kissimmee

JenniferRating, 5 stars3 weeks ago

I cannot say enough good things about Raymond & our stay. I travel a lot for my son’s lacrosse team & this was our favorite Airbnb so far! Raymond is very responsive & kind! I hope it’s available to book next year when we return.

Home in Altamonte Springs

A screened-in pool features a curvy design, surrounded by a spacious deck. The water is clear and inviting, reflecting sunlight. Lush greenery and tropical plants are visible around the pool area, creating a serene outdoor environment.

4.82 out of 5 average rating, 129 reviews

Quiet Place, convenient to everything!

FrancisRating, 5 stars1 month ago

The home is as described. Nice and Clean. Quiet neighborhood. Highly Recommend!!!!

4.96 out of 5 average rating, 103 reviews

Private Pool 4/2 Waterfront Oasis Weekly Discounts

TerryRating, 5 stars2 weeks ago

This place was great, nice pool , clean and neat, loaded with kitchen utensils and all you need to cook. The neighborhood was quiet. Overall a good place to stay

4.99 out of 5 average rating, 105 reviews

A serene outdoor area features a rectangular pool surrounded by a safety fence. A covered patio offers shaded seating, while a turquoise umbrella stands over a cushioned lounge chair. Lush greenery and landscaped gardens enhance the outdoor setting, contributing to a relaxed atmosphere.

Home in Apopka

Rate Discount~ Pool~Private Country Retreat

JillRating, 5 stars2 weeks ago

In town for a baseball tournament. Location to the fields was great — less than a 10 minute drive! Everything was clean. We enjoyed the pool after a hot day at the field. We appreciated the grill and used it to make some hamburgers and hot dogs. Kitchen was well equipped. Would definitely stay again if we need to be in the area.

4.89 out of 5 average rating, 63 reviews

Home in Casselberry

Moxy Luxe Vacation / Heated Pool/ King Bed Ste

NelsonRating, 5 stars1 week ago

Enjoyed our stay. Home was just as pictures advertised. Really quiet and peaceful neighborhood. I recommend this place.

A large, inviting pool glistens under the sun, surrounded by a spacious patio and palm trees. A stylish, shaded cabana is positioned nearby, offering a retreat for relaxation. The pool area is enclosed and features a clean white fence, enhancing the tranquil outdoor atmosphere.

4.88 out of 5 average rating, 202 reviews

Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

JoyceRating, 5 stars4 weeks ago

We where in Orlando to go to my granddaughters graduation & this home just made it a perfect vacation - so comfortable - & clean & the pool & outside area was amazing !!

A spacious pool area features a crystal-clear pool surrounded by lounge chairs and umbrellas. Lush palm trees provide shade, and a small fence enhances privacy. A gentle slope leads to a shallow section with jets, blending seamlessly into the inviting water.

4.86 out of 5 average rating, 195 reviews

Year around Heated Pool 7 min from Airport!

JoseRating, 5 stars1 week ago

Super nice, pictures do not do it justice. Upgrades clearly done little by little. Pool is amazing, outdoor area great, cozy yet spacious. Would book here again and again. 20 min from Camping World Stadium, 15 min from Downtown Orlando truly accurate, easy in and out from main road and highways.

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Condo rentals with a pool

An inviting outdoor pool area is surrounded by lounge chairs and lush greenery. The pool, featuring clear blue water, is framed by a spacious patio and a well-maintained fence. The backdrop shows a tall building with multiple balconies.

4.9 out of 5 average rating, 111 reviews

Studio near Universal Studios with great view

KinjalRating, 5 stars4 days ago

The apartment BNB was really great and exactly as described with all basic amenities provided. Super close, walkable distance, to a variety of restaurants with different cuisines. Universal Studios is a close 10 mins drive/uber ride away. The studio feels super cozy, the view from the balcony is also very nice. Laundry room is right next to the unit which was very convenient. Hosts are quick to respond to any messages/questions you may have. Enjoyed my time at this Airbnb!

4.92 out of 5 average rating, 101 reviews

An aerial view showcases the expansive pool area surrounded by lush landscaping. A large swimming pool is centrally positioned, flanked by a children's pool and numerous lounge chairs. The grounds feature walking paths and palm trees, contributing to the overall inviting atmosphere.

Condo in Orlando

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

LucindaRating, 5 stars1 week ago

Working with Isabela, was easy. The place was perfect for our needs. Beautiful, easy access to local attractions. Would highly recommend.

4.87 out of 5 average rating, 134 reviews

The outdoor pool area features clear blue water surrounded by a deck. White lounge chairs are positioned around the pool, with a fence in the background. Lush green trees and shrubbery add a natural element to the space, complemented by a bright blue sky.

Condo in Kissimmee

Near Disney/Universal Lovely 2bedroom/2bath Condo

KassidyRating, 5 stars1 week ago

The place was great! it was perfect for a quick family trip to Disney. Would highly recommend!

A well-lit pool area is featured, showcasing a curved swimming pool with clear blue water. Surrounding amenities include several lounge chairs and palm trees. The building in the background contains multiple balconies, reflecting warm light from the interior.

4.88 out of 5 average rating, 225 reviews

Maria Luz Studio-Huge Terrace/Universal area.

LisaRating, 5 stars2 weeks ago

Fantastic and Wonderful! This place has by far been the best!

4.94 out of 5 average rating, 148 reviews

The living area features a spacious gray sectional sofa accompanied by a bright blue chair. A modern wooden TV stand holds a flat-screen television. Natural light filters through large windows adorned with light curtains, complementing the neutral color palette.

Condo in Orlando

VCR2-108 Deluxe New Apartment - Convention Center

GuoRating, 5 stars1 week ago

We like this apartment very much. it's new and clean, location is also good, whole environment is good. The host reply very fast. will book it again when next time come. only not convenient is that can't stock luggage before check in and after check out.

A spacious terrace features comfortable lounge chairs with blue cushions and a stylish hanging chair. A small table accompanies two chairs, providing a perfect spot for relaxation. An umbrella offers shade, while the expansive view overlooks the surrounding area, enhancing the outdoor experience.

4.85 out of 5 average rating, 487 reviews

Modern Studio with Private Terrace near Universal

VernishaRating, 5 stars1 day ago

She was amazing! And sooo nice! We will definitely visit again!

5 out of 5 average rating, 142 reviews

The living area is furnished with a blue couch adorned with patterned pillows. Two matching wooden side tables with lamps provide soft lighting, while a wooden coffee table sits in the center. A decorative wall piece featuring palm trees adds a touch of character to the room.

Condo in Orlando

Disney & Epic Free Shuttle, Kitchen

AlizahRating, 5 stars1 week ago

Great area to stay and awesome host!

An outdoor pool area features palm trees and comfortable seating arrangements. Lounge chairs and shaded tables are positioned around the pool, which is surrounded by modern apartment buildings. A warm-toned lounge area offers additional seating, creating a welcoming space for relaxation.

4.78 out of 5 average rating, 110 reviews

LUXURY ONE BEDROOM CONDO NEAR UNIVERSAL

ShavornRating, 5 stars1 week ago

Great stay - very close to Universal and nearby attractions. Fast communication and the pool was a plus. Thank you!

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Home rentals with a private pool

A themed bedroom featuring a spacious bed with white bedding, set against a vivid space-themed mural. Two modern nightstands are flanked by unique lamps, and a large window allows natural light to illuminate the room while offering a view of the outdoors.

Villa in Four Corners

4.33 out of 5 average rating, 3 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

AurianaRating, 5 stars6 months ago

This property was very nice and matched the photos to a T. The house was spotless & very spacious. The renovated design was modern and the themed rooms were perfectly executed. The only downside was the check-in process at the gate, but after a quick phone call, the issue was resolved. I absolutely loved the space. 10/10.

4.95 out of 5 average rating, 115 reviews

Home in Davenport

Airy, Stylish Home with Pool Heat Included in Davenport

RachelRating, 5 stars1 month ago

Had a great stay at Phil's place. The home was perfect for mother's day weekend. My daughter loved the pool. The home was clean! 10/10 recommend.

Villa in Kissimmee

4.79 out of 5 average rating, 251 reviews

Visit Disney World from a Sunny Home with a Pool

ClaudiaRating, 5 stars1 month ago

I can’t say enough good things about this Airbnb – it was absolutely incredible from start to finish. The space was spotless, nicely decorated and had every amenity we could have possibly needed (and then some!). It truly felt like a home away from home, with thoughtful touches throughout that made our stay extra special. The host was communicative welcoming and very helpful!