Maitland, FL Vacation Rentals & Ski-in/Ski-out Homes
House
9.8Exceptional
(50 Reviews)
3 Bedrooms
2 Baths
8 Guests
2200 ft²
Private Pool
Hot Tub
Parking
Pool
US $410/Night
7 Nights - US $2,870
Apartment
- Orlando
- ·
- Winter Park
- 2.32 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
398.26 ft²
- Parking
- Pool
Balcony/Terrace
View
US $174/Night
7 Nights - US $1,219
Hotel
- Orlando
- ·
- Altamonte Springs
- 0.26 mi to center
9.4Exceptional
(1004 Reviews)
1 Bath
Breakfast- Parking
- Pool
Kitchen
US $239/Night
7 Nights - US $1,670
New
Hotel
- Orlando
- ·
- Winter Park
- 1.71 mi to center
1 Bath
448 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $549/Night
7 Nights - US $3,846
House
- Orlando
- ·
- Casselberry
- 0.87 mi to center
9.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
1689.93 ft²
- Parking
- Pool
Spa- Balcony/Terrace
US $262/Night
7 Nights - US $1,834
New
Hotel
- Orlando
- ·
- Winter Park
- 1.71 mi to center
1 Bath
435 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $540/Night
7 Nights - US $3,783
New
Hotel
- Orlando
- ·
- Winter Park
- 1.71 mi to center
1 Bath
323 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $472/Night
7 Nights - US $3,304
New
Hotel
- Orlando
- ·
- Winter Park
- 1.71 mi to center
1 Bath
350 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $472/Night
7 Nights - US $3,304
New
Hotel
- Orlando
- ·
- Winter Park
- 1.71 mi to center
1 Bath
350 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $436/Night
7 Nights - US $3,051
Luxury Places to Stay in Maitland
Over 345+ Luxury Places to Stay in or Near Maitland
New
House
- Orlando
- ·
- Altamonte Springs
- 1.07 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
16 Guests
- Hot Tub
- Parking
- Kitchen
Air Conditioner
US $5,583/Night
7 Nights - US $39,079
House
- Orlando
- ·
- Winter Park
- 0.95 mi to center
10.0Exceptional
(8 Reviews)
4 Bedrooms
3 Baths
12 Guests
2000 ft²
- Hot Tub
- Parking
Ocean View- View
US $714/Night
7 Nights - US $4,997
House
3 Bedrooms
2 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
Internet
US $681/Night
7 Nights - US $4,768
New
Apartment
- Orlando
- ·
- Winter Park
- 1.72 mi to center
1 Bedroom
1 Bath
2 Guests
355 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $655/Night
7 Nights - US $4,585
House
- Orlando
- ·
- Fairview Shores
- 1.15 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $611/Night
7 Nights - US $4,274
House
8.4Excellent
(5 Reviews)
6 Bedrooms
4 Baths
18 Guests
3700 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $606/Night
7 Nights - US $4,240
House
- Orlando
- ·
- Winter Park
- 0.57 mi to center
5 Bedrooms
4 Baths
10 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $602/Night
7 Nights - US $4,215
House
- Orlando
- ·
- Altamonte Springs
- 1.47 mi to center
10.0Exceptional
(11 Reviews)
5 Bedrooms
4 Baths
15 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $562/Night
7 Nights - US $3,934
House
10.0Exceptional
(12 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $554/Night
7 Nights - US $3,875
Top-Rated Vacation Rentals with a Pool in Maitland
Over 116+ Top-Rated Vacation Rentals with a Pool in or Near Maitland
House
10.0Exceptional
(31 Reviews)
4 Bedrooms
4 Baths
10 Guests
2800 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $432/Night
7 Nights - US $3,022
House
- Orlando
- ·
- Casselberry
- 0.91 mi to center
10.0Exceptional
(13 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $350/Night
7 Nights - US $2,449
House
- Orlando
- ·
- Casselberry
- 0.85 mi to center
10.0Exceptional
(10 Reviews)
4 Bedrooms
2 Baths
14 Guests
2465 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $429/Night
7 Nights - US $3,004
House
- Orlando
- ·
- Altamonte Springs
- 0.78 mi to center
10.0Exceptional
(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $369/Night
7 Nights - US $2,585
House
- Orlando
- ·
- Altamonte Springs
- 0.31 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
5 Guests
830 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $154/Night
7 Nights - US $1,076
Apartment
- Orlando
- ·
- Winter Park
- 2.16 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1950 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $282/Night
7 Nights - US $1,972
Apartment
- Orlando
- ·
- Fairview Shores
- 0.43 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
205 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $64/Night
7 Nights - US $445
House
- Orlando
- ·
- Winter Park
- 2.38 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
2507 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $410/Night
7 Nights - US $2,872
House
- Orlando
- ·
- Winter Park
- 2.17 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Pool
- Kitchen
- Internet
Pet Friendly
US $171/Night
7 Nights - US $1,195
Pet-Friendly Vacation Rentals in Maitland
Over 129+ Pet-Friendly Vacation Rentals in or Near Maitland
New
Cottage
- Orlando
- ·
- Winter Park
- 2.28 mi to center
10.0Exceptional
(37 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $146/Night
7 Nights - US $1,024
Apartment
9.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
495.14 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $128/Night
7 Nights - US $896
House
- Orlando
- ·
- Northwest Orlando
- 2.46 mi to center
2 Bedrooms
1 Bath
8 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $372/Night
7 Nights - US $2,607
House
- Orlando
- ·
- Winter Park
- 0.96 mi to center
10.0Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
11 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $263/Night
7 Nights - US $1,843
House
- Orlando
- ·
- Winter Park
- 0.87 mi to center
9.0Exceptional
(1 Review)
1 Bedroom
3 Baths
12 Guests
2002.09 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $349/Night
7 Nights - US $2,444
House
- Orlando
- ·
- Eatonville
- 0.27 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $451/Night
7 Nights - US $3,158
Apartment
- Orlando
- ·
- Winter Park
- 2.16 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
1252 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $148/Night
7 Nights - US $1,035
House
- Orlando
- ·
- Winter Park
- 2.42 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $142/Night
7 Nights - US $995
House
- Orlando
- ·
- Winter Park
- 2.24 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
890 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $125/Night
7 Nights - US $877
Large Vacation Homes & Villas in Maitland
Over 35+ Large Vacation Homes & Villas in or Near Maitland
House
- Orlando
- ·
- Casselberry
- 0.94 mi to center
10.0Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
11 Guests
1313 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $232/Night
7 Nights - US $1,623
House
- Orlando
- ·
- Winter Park
- 1.12 mi to center
1.0Average
(1 Review)
5 Bedrooms
2 Baths
11 Guests
96.88 ft²
- Parking
- Air Conditioner
- Pet Friendly
- Child Friendly
US $71/Night
7 Nights - US $498
House
9.8Exceptional
(170 Reviews)
5 Bedrooms
4 Baths
8 Guests
2800 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $447/Night
7 Nights - US $3,132
House
- Orlando
- ·
- Winter Park
- 1.12 mi to center
1 Bedroom
2 Baths
11 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $445/Night
7 Nights - US $3,112
House
9.8Exceptional
(42 Reviews)
6 Bedrooms
3 Baths
14 Guests
2500 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $499/Night
7 Nights - US $3,492
House
9.8Exceptional
(21 Reviews)
4 Bedrooms
2 Baths
10 Guests
2609 ft²
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $335/Night
7 Nights - US $2,342
Villa
- Orlando
- ·
- Altamonte Springs
- 1.27 mi to center
9.4Exceptional
(8 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $194/Night
7 Nights - US $1,355
House
- Orlando
- ·
- Winter Park
- 1.02 mi to center
8.0Excellent
(4 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $313/Night
7 Nights - US $2,191
House
- Orlando
- ·
- Fairview Shores
- 1.78 mi to center
8.0Excellent
(2 Reviews)
3 Bedrooms
2 Baths
11 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $332/Night
7 Nights - US $2,323
Wheelchair Accessible Vacation Homes in Maitland
Over 59+ Wheelchair Accessible Vacation Homes in or Near Maitland
Apartment
- Orlando
- ·
- Winter Park
- 2.72 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
7 Guests
900 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $324/Night
7 Nights - US $2,265
Hotel
- Orlando
- ·
- Winter Park
- 1.75 mi to center
9.3Exceptional
(189 Reviews)
1 Bath
380.77 ft²
- Breakfast
EV Charge Station- Parking
- Pool
US $518/Night
7 Nights - US $3,627
Hotel
- Orlando
- ·
- Altamonte Springs
- 0.25 mi to center
9.4Exceptional
(993 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $120/Night
7 Nights - US $839
New
Apartment
1 Bedroom
1 Bath
2 Guests
506 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $288/Night
7 Nights - US $2,016
Hotel
9.0Exceptional
(209 Reviews)
10 Baths
3825.49 ft²
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $152/Night
7 Nights - US $1,065
New
Apartment
- Orlando
- ·
- Altamonte Springs
- 0.50 mi to center
1 Bedroom
1 Bath
2 Guests
527 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $259/Night
7 Nights - US $1,812
New
Apartment
1 Bedroom
1 Bath
2 Guests
301 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $227/Night
7 Nights - US $1,586
New
Apartment
- Orlando
- ·
- Altamonte Springs
- 0.26 mi to center
1 Bedroom
1 Bath
2 Guests
258 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $226/Night
7 Nights - US $1,581
New
Apartment
- Orlando
- ·
- Altamonte Springs
- 0.15 mi to center
1 Bedroom
1 Bath
2 Guests
398 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $223/Night
7 Nights - US $1,558
Maitland Resorts and Airbnb Homes Under $200
Over 180+ Maitland Resorts and Airbnb Homes Under $200
House
- Orlando
- ·
- Altamonte Springs
- 0.89 mi to center
10.0Exceptional
(104 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $100/Night
7 Nights - US $701
Apartment
9.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
920.32 ft²
- Air Conditioner
- Internet
- Child Friendly
Wellness Facilities
US $157/Night
7 Nights - US $1,096
Hotel
- Orlando
- ·
- Fairview Shores
- 0.61 mi to center
9.2Exceptional
(35 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $141/Night
7 Nights - US $984
Apartment
- Orlando
- ·
- Fairview Shores
- 0.43 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
205 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $64/Night
7 Nights - US $445
House
- Orlando
- ·
- Winter Park
- 2.48 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
5 Guests
495.14 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $94/Night
7 Nights - US $658
Apartment
- Orlando
- ·
- Fairview Shores
- 0.43 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
205 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $64/Night
7 Nights - US $445
Apartment
- Orlando
- ·
- Winter Park
- 2.16 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
952 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $137/Night
7 Nights - US $958
House
- Orlando
- ·
- Northwest Orlando
- 2.62 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $196/Night
7 Nights - US $1,375
House
- Orlando
- ·
- Winter Park
- 1.75 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $188/Night
7 Nights - US $1,317
Instantly Bookable Vacation Homes in Maitland
Over 168+ Instantly Bookable Vacation Homes in or Near Maitland
Apartment
10.0Exceptional
(110 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $347/Night
7 Nights - US $2,432
New
House
- Orlando
- ·
- Casselberry
- 1.28 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $219/Night
7 Nights - US $1,530
Apartment
- Orlando
- ·
- Winter Park
- 2.16 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1950 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $210/Night
7 Nights - US $1,469
New
Apartment
- Orlando
- ·
- Winter Park
- 2.83 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
675 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $313/Night
7 Nights - US $2,191
House
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $328/Night
7 Nights - US $2,293
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1119 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $205/Night
7 Nights - US $1,435
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
797 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $169/Night
7 Nights - US $1,181
Apartment
- Orlando
- ·
- Winter Park
- 2.19 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
952 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $153/Night
7 Nights - US $1,071
Apartment
- Orlando
- ·
- Winter Park
- 2.20 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
894 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $130/Night
7 Nights - US $910
Book a Last Minute Place to Stay in Maitland
About Maitland Vacation Rentals
Explore over 354 vacation rentals in Maitland with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Maitland for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Maitland. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Maitland tailored to your preferences. On average, these rentals offer 628.8 ft² of space, and are priced at an average of US $241 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Maitland at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Maitland
| Type | Count |
|---|---|
| Vacation Homes | 161 |
| Holiday Apartments | 108 |
| Villas | 6 |
| Cottages | 4 |
Use these Quick Filters to Find a Vacation Rental in Maitland
★ Pro Tip: Discover Your Ideal Vacation Rental in Maitland with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Maitland, FL
View the weather forecast for Maitland before booking your Maitland Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Maitland, FL
Sunski offers a large selection of top attractions around Maitland . Research things to do on your vacation before you visit Maitland.
Other Places to Stay in Maitland, FL
Frequently Asked Questions About Maitland?
What are the top vacation rentals in Maitland?
When organizing your trip to Maitland, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Maitland. Peruse our collection of highly-rated properties and secure your reservation today.
- Stylish Boutique Guest house in Winter Park
- SPRING LAKE GETAWAY SUITE (Detached Guest House)
- Incredible Private Lakefront Cottage Retreat
- A curated stay in the Historic College Quarter
- Casa Jardin
- Wana Chill Spot w/Pool, Spa, Bar ,Ping Pong, BBQ
- Lakefront Paradise Near Attractions
- Remodeled Home in the Orlando area w/Fire Pit! Close to Universal and Disney!
- Brand New Luxury Modern 5BR/4.5BA+Game Room Home
- The Soundwave Retreat 🌴 Pool, Spa & Golf Oasis
How many vacation rentals have private pools in Maitland?
Uncover 16 vacation rentals boasting private pools near Maitland. Explore top-rated RBO homes offering access to a swimming pool:
- Casselberry escape w/pool & backyard
- SpringHill Suites Orlando Altamonte Springs/Maitland
- Charming and Cozy home in Altamonte Springs
- Next Level Orlando: Space Surf Springs Pool+Games
Which vacation homes or resorts in Maitland are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Maitland. Enjoy great views, locations and save money with SunSki Resorts.™
- Incredible Private Lakefront Cottage Retreat
- 3brdrm home near Downtown Orlando and Winterpark
- Hilton Garden Inn Winter Park
How many SunSkiResorts vacation rentals or resorts are available in Maitland?
Discover the ideal vacation rental in Maitland with SunSki Resorts™. We provide an extensive selection of over 354 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Maitland.
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