
Vacation rentals in Maitland
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Top-rated vacation rentals in Maitland
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

"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.

Oasis Garden Cottage -cozy, chic, near everything!
Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

The Lake House
Welcome to the mid-century Lake House. 370 square feet apartment with a private entrance and original terrazzo floors. Located on a quiet residential street on a small lake, and located within a 5-minute drive to anything you may need! Starbucks and Panera are within walking distance, and dozens of other places to eat. Publix, Walgreens, and Sprouts are just around the corner. A short 10 minute drive to the famous Park Ave, in Downtown Winter Park with shopping and gourmet restaurants.

Cozy 2/2 Home - Downtown Winterpark/Orlando
You will be close to everything when you stay at this centrally-located bungalow. Located right off I-4, 5 minutes from Advent Health Hospital, you will be 5 minutes from Downtown Orlando an, 10 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! Dubsdread golf course within walking distance! Large 70 inch 4K tv with surround sound, large sofa to enjoy watching your favorite movies, 2 rooms with queen beds, and 2 bathrooms equipped with bluetooth music

New Mid Century-Modern Studio
Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

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.

Private entrance/bathroom 10 min from DT Orlando
Welcome to your home away from home! Our cozy room with a attached bathroom is the perfect retreat for your visit to Orlando. Located just 10min from downtown Orlando, 30min from MCO and Disney, and 20 min from Universal, you'll have the best of both worlds - convenience and comfort. Whether you're here for business or pleasure, our room is the perfect place to call your temporary home. Book your stay with us today and experience the best of our city.

Priv. Modern Cozy CP 1B/1Ba Suite near DT Orl & WP
Private & Comfortable 1 bd/ba suite in a 2021 townhome with front view windows, queen size bed, walk-in shower& private entrance. Equipped w/ ceiling and portable fans, Roku smart TV, mini fridge/freezer, microwave, and Keurig. Located in a safe, quiet, walkable neighborhood. 5 minutes of College Park shops, 10 minutes from downtown Orlando, 25 minutes to Universal Studios, 30 minutes to Orlando International Airport, & 40 minutes to Disney.

Trendy Downtown Orlando Oasis
Updated three-bedroom home, only minutes from I-4, which means easy access to your favorite spots in and around Orlando. - Winter Park Village: 5 minutes - Downtown Orlando: 10 minutes - Amway Center and Camping World Stadium: 10 minutes - Disney World, Universal Studios, and I-Drive: 20 minutes Perfect for groups or families. Plenty of free parking in driveway and curb side. No parties or events please. Orlando Permit #: STR – 1094537.

Private 1-bd Mid-Century Guesthouse
Welcome to our tranquil & private 1-bd Mid-Century Modern Guesthouse. The space has a separate entrance and keyless access. Full kitchen, living room, bedroom and bathroom. Centrally located in Florida, our guesthouse offers easy access to the surrounding areas. Lots of museums, nature walks, parks & fantastic places to eat. Book now & experience the love & care we have put into our property!
Popular amenities for Maitland vacation rentals
Other great vacation rentals in Maitland

Lovely Winter Park Home close to Hospitals !

8th Green Cottage - A relaxing oasis in the city

Chic Studio Near UCF – For Solo Guests & Couples

Cozy home 5min to Park Ave and Downtown Orlando

Cozy Cottage in College Park.

King/Queen Bungalow w/ porch | central vibey area

Lakefront House ~ Pool ~ 5 Star Location

Location, Location, Location!
When is the best time to visit Maitland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$21,151 GYD | G$19,266 GYD | G$18,848 GYD | G$18,010 GYD | G$16,753 GYD | G$13,612 GYD | G$18,638 GYD | G$17,800 GYD | G$18,638 GYD | G$19,895 GYD | G$19,895 GYD | G$19,895 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 |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Maitland?
Yes! Work meets play with ease at over 60 vacation rentals in Maitland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Maitland have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Maitland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maitland have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Maitland. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Maitland?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, over 10 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Maitland?
Maitland has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Maitland?
Experience the best of Maitland with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Maitland vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Maitland, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Maitland?
Four-legged friends are welcome in Maitland. Choose from more than 40 vacation rentals for guests traveling with pets.
Do apartment rentals in Maitland have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Maitland. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Maitland?
Make yourself at home in Maitland by choosing from our most frequently booked neighborhoods. We have over 460 vacation rentals in Eatonville, and over 730 vacation rentals in Maitland.
Quick stats about vacation rentals in Maitland

Total vacation rentals
Explore 110 vacation rentals in Maitland

Nightly prices starting at
Maitland vacation rentals start at G$4,188 GYD per night before taxes and fees

Verified guest reviews
Over 5,220 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
110 of Maitland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Maitland rentals

4.8 Average rating
Maitland stays are highly rated by guests—averaging 4.8 out of 5!
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- Orange County Convention Center
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- Disney's Animal Kingdom Theme Park
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