Seasons Holiday Rentals
House
10.0Exceptional
(23 Reviews)
4 Bedrooms
3 Baths
10 Guests
2365 ft²
Private Pool
Hot Tub
Fireplace/Heating
Pool
US $236/Night
7 Nights - US $1,654
House
10.0Exceptional
(3 Reviews)
1 Bedroom
3 Baths
8 Guests
1937.5 ft²
Oceanfront- Hot Tub
Spa- Fireplace/Heating
US $271/Night
7 Nights - US $1,899
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $667/Night
7 Nights - US $4,671
Villa
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
1940 ft²
- Private Pool
- Fireplace/Heating
- Pool
Ocean View
US $360/Night
7 Nights - US $2,523
House
9.5Exceptional
(16 Reviews)
4 Bedrooms
3 Baths
8 Guests
1937.5 ft²
- Fireplace/Heating
Pet Friendly
Parking
Air Conditioner
US $366/Night
7 Nights - US $2,565
Villa
9.6Exceptional
(142 Reviews)
6 Bedrooms
5 Baths
13 Guests
2827 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $315/Night
7 Nights - US $2,202
Villa
9.6Exceptional
(105 Reviews)
4 Bedrooms
3 Baths
8 Guests
1940 ft²
- Private Pool
- Fireplace/Heating
- Pool
Balcony/Terrace
US $169/Night
7 Nights - US $1,186
House
9.6Exceptional
(28 Reviews)
4 Bedrooms
3 Baths
8 Guests
1 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $202/Night
7 Nights - US $1,413
House
8.4Excellent
(8 Reviews)
3 Bedrooms
2 Baths
10 Guests
1295 ft²
- Fireplace/Heating
- Pet Friendly
Kitchen- Parking
US $295/Night
7 Nights - US $2,062
Luxury Holiday Rentals in Seasons
Over 59+ Luxury Holiday Rentals in or Near Seasons
House
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $902/Night
7 Nights - US $6,314
House
6.0Good
(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $769/Night
7 Nights - US $5,384
House
8.4Excellent
(6 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $634/Night
7 Nights - US $4,435
House
1 Bedroom
4 Baths
12 Guests
2281.95 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $552/Night
7 Nights - US $3,863
House
5 Bedrooms
5 Baths
10 Guests
2000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $521/Night
7 Nights - US $3,650
House
6 Bedrooms
4 Baths
12 Guests
1722.23 ft²
- Pool
- Parking
- Air Conditioner
Internet
US $437/Night
7 Nights - US $3,060
House
1 Bedroom
2 Baths
9 Guests
1399.31 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $358/Night
7 Nights - US $2,505
House
8.5Fabulous
(2 Reviews)
1 Bedroom
5 Baths
13 Guests
2906.26 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $339/Night
7 Nights - US $2,373
Villa
8.2Excellent
(4 Reviews)
6 Bedrooms
5 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Internet
US $333/Night
7 Nights - US $2,330
Top-Rated Holiday Rentals with a Pool in Seasons
Over 43+ The Best Private Villas and Holiday Rentals in Seasons with a Pool
Villa
9.5Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
1937.5 ft²
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
US $239/Night
7 Nights - US $1,672
House
8.8Fabulous
(10 Reviews)
6 Bedrooms
5 Baths
13 Guests
2830.91 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $250/Night
7 Nights - US $1,750
Villa
8.7Fabulous
(3 Reviews)
1 Bedroom
3 Baths
9 Guests
2152.78 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $152/Night
7 Nights - US $1,064
House
8.0Excellent
(8 Reviews)
7 Bedrooms
5 Baths
14 Guests
3315.28 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $309/Night
7 Nights - US $2,165
House
8.0Excellent
(1 Review)
4 Bedrooms
3 Baths
9 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $230/Night
7 Nights - US $1,607
House
7.0Very Good
(12 Reviews)
7 Bedrooms
5 Baths
14 Guests
3314 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $305/Night
7 Nights - US $2,135
House
6.9Good
(16 Reviews)
4 Bedrooms
3 Baths
8 Guests
20881.99 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $245/Night
7 Nights - US $1,717
House
6.0Good
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Pool
- Kitchen
- Parking
US $301/Night
7 Nights - US $2,106
House
5.4Average
(3 Reviews)
4 Bedrooms
3 Baths
10 Guests
1940 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
US $291/Night
7 Nights - US $2,036
Pet-Friendly Holiday Rentals in Seasons
Over 11+ Pet-Friendly Holiday Rentals in or Near Seasons
House
4 Bedrooms
3 Baths
8 Guests
1938 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $271/Night
7 Nights - US $1,895
House
1 Bedroom
1 Bath
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $198/Night
7 Nights - US $1,389
House
10.0Exceptional
(10 Reviews)
5 Bedrooms
4 Baths
12 Guests
2286 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $518/Night
7 Nights - US $3,629
House
4.5Average
(15 Reviews)
4 Bedrooms
3 Baths
8 Guests
2300 ft²
- Private Pool
- Pool
- Pet Friendly
- Kitchen
US $140/Night
7 Nights - US $980
Villa
4.0Average
(1 Review)
5 Bedrooms
4 Baths
10 Guests
2286 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $201/Night
7 Nights - US $1,407
House
4 Bedrooms
3 Baths
8 Guests
1938 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $271/Night
7 Nights - US $1,897
House
5 Bedrooms
3 Baths
8 Guests
1938 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $236/Night
7 Nights - US $1,655
House
4 Bedrooms
3 Baths
6 Guests
2174 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $197/Night
7 Nights - US $1,377
House
4 Bedrooms
3 Baths
13 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $953/Night
7 Nights - US $6,674
Large Holiday Rentals and Private Villas in Seasons
Over 18+ Large Holiday Rentals and Private Villas in or Near Seasons
Villa
4.0Average
(3 Reviews)
6 Bedrooms
5 Baths
12 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
US $230/Night
7 Nights - US $1,610
House
4 Bedrooms
3 Baths
10 Guests
1937.5 ft²
- Fireplace/Heating
- Pool
- Parking
- Internet
US $283/Night
7 Nights - US $1,979
Villa
4.0Average
(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Internet
Child Friendly
Security/Safety
US $141/Night
7 Nights - US $984
Villa
1 Bedroom
3 Baths
8 Guests
1937.5 ft²
- Spa
- Fireplace/Heating
- Parking
- Air Conditioner
US $257/Night
7 Nights - US $1,796
House
6 Bedrooms
4 Baths
12 Guests
1722 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $318/Night
7 Nights - US $2,224
Villa
5 Bedrooms
3 Baths
8 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $251/Night
7 Nights - US $1,759
House
6.0Good
(5 Reviews)
7 Bedrooms
6 Baths
14 Guests
2881 ft²
- Private Pool
- Spa
- Pool
- Balcony/Terrace
US $192/Night
7 Nights - US $1,344
House
3.0Average
(1 Review)
6 Bedrooms
6 Baths
12 Guests
2850 ft²
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $180/Night
7 Nights - US $1,260
House
18 Bedrooms
18 Baths
- Child Friendly
US $737/Night
7 Nights - US $5,159
Wheelchair Accessible Holiday Homes in Seasons
Over 1+ Wheelchair Accessible Holiday Homes in or Near Seasons
House
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Pool
Breakfast- Kitchen
US $314/Night
7 Nights - US $2,196
Seasons Private Villas and Holiday Homes Under $200
Over 9+ Seasons Private Villas and Holiday Homes Under $200
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $184/Night
7 Nights - US $1,287
House
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $159/Night
7 Nights - US $1,111
Villa
3 Bedrooms
3 Baths
8 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $175/Night
7 Nights - US $1,225
House
4 Bedrooms
3 Baths
8 Guests
1600 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $168/Night
7 Nights - US $1,176
House
4 Bedrooms
3 Baths
8 Guests
1938 ft²
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $149/Night
7 Nights - US $1,043
House
4 Bedrooms
3 Baths
8 Guests
1940 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $138/Night
7 Nights - US $966
House
4 Bedrooms
3 Baths
8 Guests
1940 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $138/Night
7 Nights - US $966
House
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $198/Night
7 Nights - US $1,383
House
6.8Good
(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Pool
- Kitchen
- Parking
- Air Conditioner
US $125/Night
7 Nights - US $877
Instantly Bookable Holiday Homes in Seasons
Over 8+ Instantly Bookable Holiday Homes in or Near Seasons
House
4 Bedrooms
3 Baths
8 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $224/Night
7 Nights - US $1,566
House
1 Bedroom
3 Baths
8 Guests
1938 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $203/Night
7 Nights - US $1,423
House
7 Bedrooms
6 Baths
16 Guests
30505 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $404/Night
7 Nights - US $2,828
House
9.6Exceptional
(15 Reviews)
7 Bedrooms
5 Baths
14 Guests
2834 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $285/Night
7 Nights - US $1,995
House
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
1844 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $220/Night
7 Nights - US $1,537
House
4 Bedrooms
3 Baths
12 Guests
1844 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $287/Night
7 Nights - US $2,006
House
4 Bedrooms
3 Baths
9 Guests
1582 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $225/Night
7 Nights - US $1,572
House
4 Bedrooms
3 Baths
13 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $355/Night
7 Nights - US $2,487
Book a Last Minute Place to Stay in Seasons
About Casai's Private Villas and Holiday Rentals in Seasons
Discover more than 68 vacation rentals available in Seasons. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Seasons.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Seasons, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Seasons. On average, places to stay near Seasons offer 1986.44 ft², with nightly prices averaging US $306.
With Casai, finding and comparing holiday rentals in Seasons is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Seasons
| Type | Count |
|---|---|
| Vacation Homes | 53 |
| Villas | 14 |
Use these Quick Filters to Find a Holiday Rental in Seasons
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Seasons.
Weather in Seasons, FL
View the weather forecast for Seasons before booking your Seasons 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
Frequently Asked Questions About Seasons?
What are the top holiday rentals in Seasons?
With numerous options available in Seasons, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Seasons:
- Kissimmee 9 miles from Disney! Private pool-hot tub, spacious house and yard.
- South Facing Pool with Spa and a Game Room in Prime Location Near Disney
- Jasmine 4 Bedrooms
- Family Home with Pool, Game Room and Disney Nearby
- Large 6 bed, top level comfort, pool, close to the parks & superb lake view!
- Private Pool Villa close to Disney Parks with free Wifi and BBQ
- 4BR Disney Oasis: Private Screened Pool + FREE Pool Heat! (20 Min to Parks)
- 4 BR No carpet Just Remodeled Unit SR1205
- Private Pool Home at Seasons Community
- Seasons Villa 6 bedrooms, 4 masters and water view
Which holiday homes in Seasons are best for families?
If you're searching for a family-friendly holiday home in Seasons, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Seasons:
- Luxurious Lake Berkley Townhome minutes away from Disney Parks and Shopping
- Single-Story 4BR Home w/Pool & Game Room
- Luxury 4 Bedroom Villa in Kissimmee near Disney
How many Casai.com holiday rentals are available in Seasons?
As of 2026, Casai boasts over 68 properties listed in the Seasons area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Seasons.
People Also Ask
Finding the best prices in Seasons
Map
