Vacation rentals with a pool in Maitland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Maitland

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 159 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!

Guest favorite

Guest suite in College Park

4.91 out of 5 average rating, 132 reviews

Lakefront Artist's Studio- Isolate in Luxury!

Our lakefront Artist Studio Apartment is ideal for those who want/need isolation or just enjoy privacy in a beautiful setting. Spend your days working on the high speed internet poolside or on the private covered porch, and evenings sipping wine and watching the sun set over Lake Silver. The entrance is private and decor modern, a bit boho, and showcases my artwork. Sleep well in the pillow-top queen bed and sip your morning coffee in the butterfly garden. *hospital grade cleaners utilized

Guest favorite

Home in Apopka

4.88 out of 5 average rating, 119 reviews

Country Pool home on 2 acres-30 minutes to Disney

Relax with friends and family at this country pool home just northwest of Orlando and all of the attractions! 30 minutes to Disney and Universal Studios. 10 minutes to Historic Mount Dora. 8 minutes to Kelly Park/Rock Springs Run. One hour to Daytona Beach. What a great location and place to stay to explore Central Florida! Pets are welcome! 3 queen beds and a couch! (The hot tub you might see in a photo is not advertised because it is not operational but the pool is very refreshing/not heated)

Guest favorite

Bungalow in Maitland

4.87 out of 5 average rating, 527 reviews

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.

Guest favorite

Guest suite in Oviedo

4.92 out of 5 average rating, 367 reviews

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

Guest favorite

Guest suite in Thornton Park

4.97 out of 5 average rating, 201 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.

Guest favorite

Home in Maitland

4.84 out of 5 average rating, 104 reviews

Bonheur Ala Maison - Boasts beauty comfort extras

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!

Superhost

Guesthouse in Orlando

4.87 out of 5 average rating, 258 reviews

Couples Oasis *Heated Pool* and Lake View

Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house. *Heated Pool* available for $20 fee for first day and $10 every extra day.

Guest favorite

Farm stay in Oviedo

4.9 out of 5 average rating, 105 reviews

The Guest House in Oviedo countryside

If you love farm life, The Guest House is the place for you! We invite you to stay in the 600 sq ft apartment, one bedroom & one full bath. Our cozy country getaway is clean, fully furnished & situated on a 5-acre working equine therapy ranch. During your stay, you'll hear all the neighs, moos, bleats and clucks your heart desires! Come see a real farm in action from the comfort of a relaxing space, or while dining al fresco as you enjoy watching the horses go in and out of pasture.

Guest favorite

Guest suite in Maitland

4.79 out of 5 average rating, 239 reviews

Guesthouse w/Private Indoor Pool

Hello! This is our AirBnB's located in the heart of Orlando, in a private home-owned community. It comes with a private indoor swimming pool, ping pong table and a pool table! Beautiful Modern Comfy guest house in a private quiet neighborhood, perfect for couple and family. Newly Renovated with private parking. Everything you see in the pictures is a part of your Airbnb exclusively. NOTE: we have this same Airbnb but for a lower rate which excludes the recreational area and indoor pool

Guest favorite

Home in Maitland

4.94 out of 5 average rating, 156 reviews

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Guest favorite

Guest suite in Altamonte Springs

4.96 out of 5 average rating, 314 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