Cruise And Resorts - Vacation Rentals in Seasons

Luxury Places to Stay in Seasons

Over 69+ Luxury Places to Stay in or Near Seasons
Summer Breeze From US $902
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Tiger Lilly House 6 Bedroom From US $756
         

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6.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Jasmine 4 Bedrooms From US $726
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Allamanda Holiday Home 4 Bedroom From US $581
         

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8.4 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
6 Bedrooms/4.5 Bathrooms Seasons (1270 SB) From US $465
         

6 Bedrooms 45 Bathrooms Seasons 1270 Sb From US $437
         

Top-Rated Vacation Rentals with a Pool in Seasons

Over 57+ Top-Rated Vacation Rentals with a Pool in or Near Seasons
South Facing Pool with Spa and a Game Room in Prime Location Near Disney From US $271
         

Kissimmee Getaway with Pool about 7 Mi to Disney! From US $283
         

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10.0 (1 Review)
House
  • Parking
  • Pool
  • Accessibility
FREE POOL HEAT Spacious 4 BR Pool Home From US $216
         

9.8 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Private Pool Villa close to Disney Parks with free Wifi and BBQ From US $180
         

9.6 (99 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Kissimmee Home w/Pool < 9 Mi to Disney World! From US $285
         

9.6 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Resort Townhome 4BR, Private Pool, Near Disney From US $221
         

9.2 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Seasons

Over 15+ Pet-Friendly Vacation Rentals in or Near Seasons
4 BR No carpet Just Remodeled Unit SR1205 From US $146
         

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8.6 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Entertaining Game Room 4BR Near Disney From US $329
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Entertaining Game Room 4BR Near Disney From US $199
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sun-Drenched Escapes: Discover 2025 Florida's Best Rentals! From US $518
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Seasons on PetFriendly.io

Large Vacation Homes & Villas in Seasons

Over 25+ Large Vacation Homes & Villas in or Near Seasons
S890SB - 12 guests - 6 beds From US $327
         

8.7 (3 Reviews)
Villa
  • Parking
  • Pool
  • Security/Safety
Kissimmee Getaway w/Pool ~ 7 Mi to Disney! From US $255
         

5.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
6 bedrooms pool villa with game room From US $224
         

4.0 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
VR Jungle 2 Jungle with Disney's Tarzan & More! From US $198
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Seasons

Over 1+ Wheelchair Accessible Vacation Homes in or Near Seasons

Seasons Varoom and Airbnb Places to Stay Under $200

Over 16+ Seasons Varoom and Airbnb Places to Stay Under $200
Disney Area Villa South-Facing Pool and Spa Game Room From US $152
         

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8.7 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Cherry Blossom From US $159
         

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New
House
  • Air Conditioner
  • Parking
  • Pool
Beautiful Townhouse In Bella Vida Resort From US $144
         

4.0 (16 Reviews)
House
  • Air Conditioner
  • Pool
  • Private Pool
Bright 6 bedroom pool home in Kissimmee - Spa and games room From US $180
         

Cristine's Seasons Vacation Home From US $149
         

Instantly Bookable Vacation Homes in Seasons

Over 8+ Instantly Bookable Vacation Homes in or Near Seasons
Cozy townhouse close to all attractions From US $211
         

Seasons Retreat, 5 Bed, 4 Bath, Private Pool Villa From US $201
         

4.0 (1 Review)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool
Aladin Cozy Bella Vida Kissimmee Disney From US $370
         

4BR Near Disney Bella Vida Resort Pool BBQGrilln From US $355
         

Entertaining Game Room 4BR Near Disney SR1205 From US $236
         

Free WIFI - Near Disney - Private Pool From US $203
         

About Seasons Vacation Rentals

With more than 69 Seasons vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cruiseandresorts and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Seasons.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruiseandresorts Seasons, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Seasons. Places to stay near Seasons

Cruiseandresorts makes it easy and safe to find and compare vacation rentals in Seasons with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Pro Tip: Cruiseandresorts makes it easy to compare the best listings on Cruiseandresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruiseandresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Seasons.

Weather in Seasons

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