Holiday rentals with a pool in Orlando

4.98 out of 5 average rating, 132 reviews

Private Rooftop Suite! No resort fees!

Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

A bright living area features a cozy gray sofa paired with two stylish yellow chairs. A wooden coffee table sits atop a textured area rug, while large glass doors lead to a balcony that offers views of Lake Bryan.

4.95 out of 5 average rating, 123 reviews

Modern Lake view Condo 1 mile from Disney

You will love our updated 1 bedroom, 2 bathrooms, spacious 798 sq ft condo so close to Disney at Blue Heron Beach Resort in wonderful Lake Buena Vista, home to lots of restaurants and shopping! Enjoy spectacular sunrise views from your private balcony overlooking the lake. Resort amenities include large swimming pool, kiddie pool, hot tub, tiki bar, fitness rooms & game room. Located on peaceful Lake Bryan, you have access to water sports like kayaking, boating, jet skis & fishing on the lake.

4.98 out of 5 average rating, 164 reviews

The living area features a modern sectional sofa adorned with decorative pillows. A sleek coffee table is positioned on a patterned rug, while large sliding doors lead to a balcony, enhancing natural light. An adjacent dining area with stylish chairs is visible in the background.

Flat in Kissimmee

3121-402 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

4.84 out of 5 average rating, 213 reviews

A shaded lounging area features comfortable seating and a glass-top table, set with refreshments. In the background, a large pool glistens under the sun, surrounded by palm trees and various seating options, including cabanas and sun loungers.

Townhouse in Kissimmee

Orlando Disney ºoº 3BD in Resort | Kissimmee

Modern Townhouse in Resort w/ preserve area and Amazing Clubhouse. (NO resort fees!) | 1 min | Old Town Kissimmee | 3 min | Publix®, McDonald's®, Wendy's®, Miller's Ale House® and more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | DISNEY® AREA (All Theme Parks) | 9 min | Premium Outlet® | 11 min | Disney Springs | 11 min | ESPN® Sports | 13 min | Convention Center | 15 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 70 min | Bush Garden's® | 95 min | Sarasota & Clearwater

4.88 out of 5 average rating, 219 reviews

The open living area features a contemporary design with a curved sofa in neutral tones, two blue accent chairs, and a glass coffee table. A textured area rug complements the decor. Large windows allow natural light to illuminate the space, enhancing the connection to the outdoors.

Townhouse in Kissimmee

Adorable 2 bdr lakefront w/jacuzzi 5 min *Disney*

This townhouse provides an open main living space that allows you to connect the dining and a fully equipped kitchen. The house can accommodate up to 6 guests, divided into one luxe king en-suite, and a design theme two full en-suite. After a long day at the parks with a beautiful lakefront view, relax in your private spa. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant, and only 5 min from Disney and golfing area Free Parking Close to lakes, camping, beach, vineyards, farms

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

4.86 out of 5 average rating, 133 reviews

Stylish Condo 20 mins to Disney/King Bed

Escape to our lovely vacation villa, nestled in the vibrant heart of Orlando's premier golfing destination. Just a 7-mile drive from Disney attractions and 30 minutes from Orlando International Airport. Discover the awe-inspiring Reunion Resort, offering an array of delights. Indulge in delectable dining experiences, take a dip in sparkling pools, savor refreshing drinks at poolside bars and grill. Embark on an extraordinary getaway that exceeds all expectations. Book your stay with us today!

Guest suite in Thornton Park

A serene pool area is surrounded by a well-maintained patio with paver stones. Lush greenery and tall palm trees are visible in the background, creating a peaceful atmosphere. A staircase leads to an upper level, enhancing the outdoor space's layout.

4.97 out of 5 average rating, 246 reviews

Orlando Oasis in the heart of Thornton Park

The perfect Oasis located in the beautiful Historic Thornton Park, one of the safest and quietest neighborhoods in Downtown Orlando, this brand new studio apt is perfect for couples, business travelers, and families of 3. Enjoy custom cozy decor, a super-comfy queen bed, full kitchen amenities, and a private view of the pool & downtown skyline. Easily walk to great parks, restaurants, bars, shopping, and Lake Eola. 20 min to Universal. 25 min to Disney. *VIDEO TOUR* available on YouTube.

4.95 out of 5 average rating, 173 reviews

A modern digital door lock is mounted on a light-colored door, featuring a keypad for secure access. A blurred plant with lush green leaves is visible in the background, adding a touch of nature to the entryway.

Guest suite in Kissimmee

It's too much like a elegant mini-hotel (5)

It's too much like a elegant mini hotel with rich artistic atmosphere！ All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

The exterior of the house is viewed from the sidewalk, surrounded by neatly maintained lawns. Two large trees provide ample shade. The home features a light-colored facade and a driveway visible on the right, complemented by a two-car garage.

4.85 out of 5 average rating, 121 reviews

Harmony Place - W/ Pool - Near Walt Disney

Welcome to Harmony Place, your perfect getaway! Relax and unwind with the whole family at this serene retreat. This stunning home features a private pool, 3 spacious bedrooms, and 2 bathrooms, comfortably accommodating up to 9 guests. Located in the exclusive Crescent Lakes community in Kissimmee, Florida, you’ll be just 11 miles from Walt Disney World, 22 miles from Universal Studios, and 18 miles from SeaWorld Orlando. Enjoy nearby dining and shopping options for added convenience!

4.99 out of 5 average rating, 138 reviews

The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.

Flat in Kissimmee

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

4.96 out of 5 average rating, 101 reviews

A bright living room features large windows allowing natural light to fill the space. A sectional sofa in teal is positioned around a small table, with light wood flooring underfoot. A television sits opposite the seating area, complemented by a light ceiling fan above.

Cottage in Clermont

A-Frame Cottage near Disney, Universal, & Lakes

Come enjoy a relaxing stay at the Dragonfly Cottage and explore all that Central Florida has to offer. With Disney World just 23 miles (37 km) and Universal Studios 26 miles (42km) away, you will find plenty of entertainment. Beautiful Lake Louisa State Park is less than 3 miles (5 km) and the Downtown Clermont Lakes only 6 miles (9 km) away. With amenities like an Olympic-size pool just steps away, you'll be able to cool off and unwind after long days of sun and fun.

4.84 out of 5 average rating, 258 reviews

The studio features a king-sized bed against a city skyline mural, complemented by large windows that offer ample natural light. A cozy sitting area includes a blue couch and a circular dining table with four chairs. A decorative rug anchors the space, enhancing its elegant design.

Flat in Orlando

Small/Studio HUGE PRIVATE TERRACE ❤️❤️

Beautiful Studio with a large PRIVATE TERRACE/King side bed. Enjoy the jacuzzi bathtub!!! Our Studio is located one block from the International Dr. Orlando City. In the center of everything!!! Universal Studios Area. Washing video/YouTube https:/youtube.com/shorts/5XslwElr158?feature=share The resort has 2 open swimming pool and 1 swimming pool with a closed roof, with tempered water. This property IS NOT RECOMMENDED FOR CHILDREN, BABY’S or Pets.

Popular amenities for Orlando rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 160 reviews

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.

Home in Orlando

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

A large community pool is set amidst lush greenery, featuring sun loungers around its perimeter. A cozy living area showcases a modern sofa and a television, creating a welcoming space. A scenic view of a lake is complemented by a fountain in the background. A private hot tub invites relaxation, shaded by a colorful umbrella.

4.91 out of 5 average rating, 118 reviews

10 Min to Disney • Cozy Townhome + Jacuzzi + BBQ

The spacious living area features a light-filled environment with comfortable seating arrangements, including a sofa and armchair. A coffee table sits in the center, accompanied by a decorative bowl of sunflowers. A large television is positioned against a wall, complemented by neutral-toned decor.

4.9 out of 5 average rating, 107 reviews

4BD 2BA Kissimmee Pool House near Disney

An enclosed in-ground swimming pool is featured, surrounded by a screened lanai. Various lounge chairs and umbrellas provide seating options. The pool is clear and inviting, with a decking area that offers space for relaxation.

4.92 out of 5 average rating, 159 reviews

Disney New Neighbor

4.99 out of 5 average rating, 100 reviews

A spacious living area is furnished with a large sectional couch, accented by colorful throw pillows. A wall-mounted TV is positioned above a wooden console. Natural light filters through large windows, and the open layout connects to a dining area featuring a well-set table.

Home in Four Corners

Luxury Vacay Home w/ Pool 5Br/5Bath near Disney

4.92 out of 5 average rating, 131 reviews

Entire Modern Home near Disney • Pool & Game Room

4.97 out of 5 average rating, 144 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

4.94 out of 5 average rating, 114 reviews

The outdoor pool area features a screened enclosure with views of the golf course beyond. A circular table is set with blue napkins and dinnerware, surrounded by blue chairs. Six lounge chairs are positioned alongside the shimmering pool, providing a comfortable space to relax.

Home in Davenport

"Cozy Retreat with something for everyone"

Apartment rentals with a pool

4.91 out of 5 average rating, 182 reviews

P-Gated Resort-5 miles to Disney-2 FREE Water Park

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.

4.92 out of 5 average rating, 134 reviews

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

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.

4.84 out of 5 average rating, 118 reviews

5 mins Universal 10 mins Epic park | Rustic LOFT

An open living space features large French doors leading to a balcony, allowing natural light to brighten the area. Stylish seating is arranged around a coffee table, while artwork resembling a Marvel theme decorates a wall in the adjacent bedroom. Views of palm trees and a nearby pool can also be seen.

4.97 out of 5 average rating, 128 reviews

Golf Front Luxury Penthouse: Views, Marvel, 2Pools

A spacious living area features large windows framed by bright curtains, providing natural light. A cozy bed is adorned with themed decor, and a comfortable sofa complements the surrounding furnishings. An aerial view showcases the resort's heated pool, surrounded by lush landscaping.

4.91 out of 5 average rating, 254 reviews

Disney Oasis by the lake

A patio area is presented under a covered porch, featuring a round table set for two with a white tablecloth and colorful cups. Two comfortable chairs with blue cushions are positioned around the table. A scenic view of a lake with greenery can be seen in the background.

4.84 out of 5 average rating, 147 reviews

Stunning view, near Disney.

A spacious bedroom features a queen bed with a light gray throw blanket and decorative pillows. Twin beds are visible in the background, while artwork adorns the wall. Two bedside lamps and wooden nightstands flank the bed, complementing the warm wooden flooring.

4.89 out of 5 average rating, 138 reviews

The Point Hotel & Suites - 705H Luxury - Pool View

A dining area features a glass table surrounded by six upholstered chairs, creating a welcoming space. A sideboard is positioned against the wall, and artwork adorns the adjacent walls. Natural light filters in through a set of sliding glass doors, leading to the balcony.

4.89 out of 5 average rating, 288 reviews

Vista Cay Orlando Lakeview Condo

Other holiday rentals with a pool

4.99 out of 5 average rating, 74 reviews

A modern townhome complex sits amidst lush greenery, featuring a well-maintained lawn and trees. The buildings exhibit a sleek design with neutral-colored exterior walls and bold geometric accents. Each unit has a small porch area with seating options, enhancing the inviting atmosphere of the community.

Townhouse in Kissimmee

Rare-find! Immaculate 5-Star home 10 mi to Disney!

5 out of 5 average rating, 19 reviews

A modern living area features two sleek black sofas positioned around a circular table with a bowl of yellow fruit. A decorative wall art piece is mounted above, complemented by lamps and framed mirrors. Natural light streams through expansive windows draped in sheer curtains.

Apartment in Ventura

Modern super clean condo at Ventura Country Club !

4.87 out of 5 average rating, 69 reviews

A vibrant welcome sign for Orlando, Florida is depicted, featuring an artistic skyline with tall buildings. A colorful Ferris wheel is visible, along with various recreational activities by the water, including boats and beachgoers. Palm trees frame the scene, enhancing its lively atmosphere.

Flat in Orlando

Luxury Apt + Pool + BBQ + Gym.

A spacious living area showcases large windows that invite natural light, complemented by comfortable seating. A private pool is visible outdoors, surrounded by a screened enclosure. The bedroom features a king bed and calming decor, while another area displays two twin beds in bright, inviting colors.

5 out of 5 average rating, 36 reviews

Fun in Paradise: Pool Villa near Attractions!

4.97 out of 5 average rating, 33 reviews

A fenced heated pool area is visible, surrounded by lush greenery and palm trees. The villa entrance features a welcoming façade and a spacious driveway. Inside, a games room showcases vibrant Nemo-themed murals, along with seating and game tables for recreational enjoyment.

Home in Davenport

Adult Luxury - Magic for Families!

5 out of 5 average rating, 71 reviews

The living area features a spacious gray sectional sofa arranged around a white coffee table, with decorative items adding style. A large window provides natural light, complemented by modern shelving and a lamp. The open kitchen is visible in the background, emphasizing a comfortable layout.

Flat in Kissimmee

Modern Luxury Kissimmee Retreat

4.89 out of 5 average rating, 38 reviews

The spacious open-plan living area features a large sectional sofa, a sleek coffee table, and a wall-mounted smart TV. A dining area with stylish chairs is visible in the background, along with a modern kitchen including a dining island, illuminated by pendant lights.

Home in Davenport

Stunning and modern 4 bedroom home with pool