Holiday rentals with a pool in Oviedo

4.88 out of 5 average rating, 589 reviews

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

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.

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.

4.91 out of 5 average rating, 161 reviews

Modern Tropical House Heated Salt Pool

☞Superhost 9 years ☞ Large Salt Pool (W/ heated option $ Oct-April) ☞3 Bedroom 3 Full Bath W/extra 4th queen daybed ☞ Easy access to the 417 East West express way (toll rd.) to get around Orlando ☞Easy smart lock self Check-in ☞ Driveway Parking ☞ Luxury bedding ☞65in Smart TV with Netflix in TV room ☞Dimmer mood lighting ☞Illuminated pool & landscape lighting ☞Pool Lounge Floats ☞Full Kitchen ☞Dining & Picnic table seats 6 to 8 guests ☞Hi speed 231mb internet ☞Uber Eats Food Delivery

4.98 out of 5 average rating, 124 reviews

The exterior of the Cozy Cottage is designed with a welcoming green facade, featuring glass doors that open to a charming patio. A stone path leads to a small round table with chairs, complemented by a decorative fountain and lush greenery surrounding the area.

Bungalow in College Park

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.

Guesthouse in Lake Cherokee

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.

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.

4.98 out of 5 average rating, 121 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.

Guesthouse in Longwood

"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 suite in Altamonte Springs

A bright living area features large windows with light beige curtains, allowing natural light to fill the space. A vintage dresser is positioned next to a blue upholstered chair adorned with decorative pillows. Warm wooden flooring and an area rug add to the room's cozy atmosphere.

4.97 out of 5 average rating, 336 reviews

St. Hemingway Suite

Very tranquil Romantic Suites with views and access to large lake. PRIVATE ENTRANCE and private bathroom. Amenities include, private dock, pool, large manicured lawns, private parking, breakfast kitchenette and much more. Close to theme parks and beaches. Ample shopping and award winning restaurants very nearby. Peaceful setting to read, do Yoga, enjoy quiet moments by the lake, watch the boats sail by or watch the sun rise. Peace and tranquility at its best. We welcome you

4.92 out of 5 average rating, 439 reviews

Two sparkling glasses filled with a bright orange beverage are placed by the edge of a non-heated swimming pool. The pool area is surrounded by lush greenery and light stone walls, offering a serene outdoor retreat.

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 there is 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. Host primary residence does overlook the pool area. Listing does not include a full kitchen. Central to everything: UCF: 5 miles MCO Airport: 25 miles Sanford Airport: 11 miles Disney: 40 miles

4.9 out of 5 average rating, 270 reviews

A spacious pool area is surrounded by tropical landscaping, featuring tall palm trees and flourishing plants. The pool includes a spa with cascading water features. A bright red umbrella provides shade over a seating area, creating an inviting outdoor space for relaxation.

Home in Lake Mary

Gated community XL pool Home 2500sq/f

Our LK Mary home sits in Between the 2 most famous places central Florida has to offer, Disney World & Daytona beach and everything else in between. This property sits on 1/2acre of land, tropical landscaped backyard making your stay with us the true Floridian experience . Total privacy with quite nights for a full rest. NO BIKERS PLease! My home is in a Gated community.1 mile to Dtwn Lake Mary. Our pool is NOT heated, the hot tub only CAN be headed at an additional cost

Guest suite in Lake Underhill

A private outdoor area is showcased, featuring a sparkling pool accompanied by a hot tub. Lush greenery and colorful plants surround the space, while comfortable seating options, including bright blue chairs, invite relaxation. A pergola provides shade, enhancing the tranquil atmosphere.

4.92 out of 5 average rating, 385 reviews

Downtown Orlando Garden Retreat

This space is a mother-in-law suite, completely private from the main house, accessible through a private entrance outside and entering through the garage. THIS IS NOT THE ENTIRE HOUSE! There is a queen size bed... perfect for a couples getaway! It is conveniently located about 15 min. from OIA and 5 min. from downtown Orlando. There is a beautiful pool and hot tub with stunning sunset views of across the lake... so peaceful and you feel like you are in a resort

4.99 out of 5 average rating, 170 reviews

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 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.

4.93 out of 5 average rating, 150 reviews

A vibrant blue tiny home with a welcoming front porch is surrounded by lush greenery. Two white chairs are positioned on the wooden deck, inviting relaxation. Large windows allow natural light to fill the interior, while a light fixture hangs above the entrance.

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.

Guest suite in Winter Springs

A private pool area is enclosed by a screen, featuring a clear blue water surface. Several floats and beach balls are visible on the water, with lounge chairs and lush greenery seen in the background, offering an inviting space for relaxation.

4.92 out of 5 average rating, 132 reviews

Sierra Suite w/ Pool, Hot tub, and Sauna-Near UCF

Welcome to your home away from home! Our 1 bedroom, 1 bathroom suite offers all the amenities you need for a comfortable and relaxing stay. Enjoy a dip in the pool, soak in the hot tub, or unwind in the sauna. The bedroom has a comfortable queen size bed, and the bathroom has a shower and tub. The suite is perfect for couples or solo travelers looking for a tranquil getaway. We look forward to hosting you!

Popular amenities for Oviedo rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A serene pool area is surrounded by lush landscaping and tall palm trees, with sunlight glistening on the clear water. The pool features a gentle curve, and a white fence encloses the backyard, providing privacy and a sense of tranquility.

4.86 out of 5 average rating, 147 reviews

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

Superhost

A spacious living area is presented with a mix of comfortable seating, including a brown leather chair and a golden sofa. A decorative coffee table is placed centrally, surrounded by an area rug. Natural light enters through large windows, creating an inviting ambiance.

4.81 out of 5 average rating, 134 reviews

Orlando Family/Home /Disney / Airport / UCF / Pool

Superhost

An outdoor space features a large pool surrounded by a patio area. Comfortable seating and an umbrella are positioned under a shaded area. Lush greenery lines the back and sides, providing privacy, while the main house showcases a welcoming design with large doors leading out to the pool.

Home in Winter Park

4.86 out of 5 average rating, 115 reviews

Charming Retreat In Winter Park

4.9 out of 5 average rating, 333 reviews

A welcoming bedroom area features a queen-sized bed adorned with patterned bedding, complemented by a sliding barn door. The kitchen showcases modern appliances and a bright atmosphere. The living room includes ample seating arranged around a coffee table, while the game room offers a pool table and comfortable couches.

Home in Oviedo

🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s

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, 229 reviews

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

4.88 out of 5 average rating, 162 reviews

The exterior of a two-story Spanish Mission-style home is depicted in soft twilight. The structure features arched entryways with large windows, surrounded by lush landscaping. A decorative lantern illuminates the front entrance, enhancing the inviting charm of the property.

Home in Lake Cherokee

3,000 Sqft Historic Home With Pool Near Everything

4.97 out of 5 average rating, 130 reviews

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 Lake Formosa

Spacious Home with Pool & Hot Tub near Downtown

A spacious resort-style swimming pool is enclosed in a screened area, ensuring a bug-free experience. Comfortable lounge chairs are positioned around the pool, with a separate shallow area and a seating spot beside the water. The inviting blue waters reflect the surrounding sunlight.

4.77 out of 5 average rating, 149 reviews

3 BED/2 BATH Home with pool near Disney

Condo rentals with a pool

A spacious outdoor area features several palm trees and seating arrangements with turquoise cushions. The backdrop includes a modern multi-story building. A barbecue area is visible, and lounge chairs are positioned around a sparkling pool, creating an inviting environment for relaxation.

4.88 out of 5 average rating, 119 reviews

Luxury Condo On I-Drive & One Mile from Universal

4.84 out of 5 average rating, 110 reviews

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 !

A warm living space features a dark wooden ceiling and an accent wall with textured concrete. Comfortable seating faces a mounted television, while wooden shelves are adorned with books and decorative plants. Natural light enters through large windows, enhancing the inviting atmosphere.

4.87 out of 5 average rating, 104 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

An aerial view of the clubhouse area is displayed, featuring a large pool surrounded by lounge chairs. Palm trees provide greenery around the poolside, while guests can be seen enjoying the water. The architecture of the clubhouse complements the inviting outdoor space.

4.93 out of 5 average rating, 123 reviews

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

4.98 out of 5 average rating, 234 reviews

A modern dining area features a glass-top table surrounded by sleek white chairs. Elegant artwork adorns the brown accent wall, while natural light fills the space from sliding glass doors leading to a patio with a view of the golf course.

Condo in Four Corners

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

A modern studio presents a king-size bed with a plush gray comforter, elegantly complemented by a decorative throw. A cozy seating area features a blue tufted ottoman and stylish bar stools. Large windows allow natural light to fill the space, framed by sheer and dark curtains.

4.88 out of 5 average rating, 248 reviews

Maria Luz Studio-Huge Terrace/Universal area.

A cozy studio space is highlighted by a spacious bed adorned with a decorative blanket. A comfortable sofa and tufted stool provide additional seating. Light floods in through large windows, illuminating the soft tones of the wallpaper and area rug.

4.89 out of 5 average rating, 174 reviews

Luxury Studio, Near to Universal-Epic ,And Disney!

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.

4.99 out of 5 average rating, 160 reviews

Disney & Epic Free Shuttle, Kitchen

Home rentals with a private pool

An open living space features a comfortable beige sectional sofa with colorful accent pillows. A dining table is visible beside a modern kitchen with stainless steel appliances. Large sliding glass doors provide a view of the pool area, enhancing the connection to the outdoors.

Villa in Championsgate Village

Wr001or (1stfororlando)

A spacious living area is highlighted by a large wall-mounted TV above a modern electric fireplace. The white sectional sofa, accented with colorful pillows, faces a sleek coffee table on a patterned rug. Natural light floods in through large windows draped with light curtains.

4.14 out of 5 average rating, 7 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

The exterior of the home features a two-story structure with a light beige facade and a tiled roof. Lush landscaping, including palm trees and shrubs, enhances the entrance, while a spacious driveway leads to a two-car garage.

Beautiful 9 Br Pool Home In the Solterra Resort!

A private outdoor area showcases a pool surrounded by a sleek, turquoise enclosure. Comfortable lounge seating is present, alongside sun loungers. The spillover spa is integrated into the pool area, providing a welcoming space for relaxation. Natural light illuminates the entire setting.

7547oml-Solterra Resort

4.95 out of 5 average rating, 116 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Villa in Kissimmee

4.78 out of 5 average rating, 256 reviews

Visit Disney World from a Sunny Home with a Pool

The image displays four distinct areas of the villa. A games room features a foosball table and a billiard table with a laundry area in the background. A cozy bedroom showcases a queen bed with nightstands. A private screened pool invites relaxation. A kitchen area includes modern appliances and seating at the bar.