Big Pine Resort Cottages - Vacation Rentals in Montego Bay

5 miles from Disney & Universal! From US $110
         

10.0 (13 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
New! Family cottage near Disney-Sleep 6 From US $134
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
Lakeview Home w/Private Pool & Free Water Park! From US $640
         

|
10.0 (3 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Family-Friendly Cottage Near Orlando’s Top Attractions From US $160
         

Cozy Tiny Home Getaway Minutes from Disney From US $124
         

10.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Perfect Place for a Perfect Vacation From US $123
         

10.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Cozy Cottage Near Disney Pool, Hot Tub & Resort Amenities! From US $117
         

Luxury Places to Stay in Montego Bay

Over 10000+ Luxury Places to Stay in or Near Montego Bay
6BR Luxury Home w Private Pool & BBQ From US $5,900
         

|
New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
10BR - Family Home Near Disney with Pool & BBQ From US $5,900
         

Top-Rated Vacation Rentals with a Pool in Montego Bay

Over 10000+ Top-Rated Vacation Rentals with a Pool in or Near Montego Bay
Conservation View - Hot Tub - Free Pool Heat - Very Private From US $243
         

Pet-Friendly Vacation Rentals in Montego Bay

Over 2061+ Pet-Friendly Vacation Rentals in or Near Montego Bay
Vacation rental with a touch of Class! From US $153
         

9.6 (64 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Celebration Suites 2 Bedroom Condo From US $124
         

|
8.9 (86 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious Home Near Disney with Pool From US $910
         

New
House
  • Air Conditioner
  • Pet Friendly
  • TV
4 Bedroom Home and Private Pool, From US $247
         

8.2 (50 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Storey Lake Resort 4 Bedroom Townhome Pet Friendly From US $247
         

9.4 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
7 Bedroom Luxury Home , Sleeps 16 From US $363
         

9.0 (51 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa with Private Pool, Games Room, Free Wifi and Lake View From US $187
         

Large Vacation Homes & Villas in Montego Bay

Over 8783+ Large Vacation Homes & Villas in or Near Montego Bay
Multi Resorts at Fantasy World From US $150
         

|
7.4 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
*NEW* Super Amazing Vacation Getaway From US $977
         

9.4 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Montego Bay

Over 1830+ Wheelchair Accessible Vacation Homes in or Near Montego Bay
Fireworks @ Night -storey Lake By Shine Villas 709 2 Bedroom Apts From US $539
         

Charming Holiday Condo, Only 7 min to Disney From US $177
         

9.8 (63 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
(FG101) Storey Lake Condo 3/2, Free Waterpark From US $172
         

8.6 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Kissimmee Condo w/Resort-Style Amenities! From US $172
         

10.0 (98 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Montego Bay Varoom and Airbnb Places to Stay Under $200

Over 4736+ Montego Bay Varoom and Airbnb Places to Stay Under $200
Cozzy Townhouse! 925PTC-SVH From US $100
         

|
New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
3BR Apartment - Great Location Super Comfort From US $140
         

10.0 (1 Review)
Apartment
  • Wheelchair Accessible
  • Balcony/Terrace
  • Accessibility
Special rates available in Sep and Oct of 2026 From US $180
         

9.4 (133 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Family Resort by Disney, Roomy 2BR+Loft & 5 Pools! From US $163
         

9.8 (77 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Exquisite Destination. Bay Vista From US $185
         

9.6 (273 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Family Resort near Disney, 3BR+Loft & 5 Fun Pools! From US $167
         

9.4 (47 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Montego Bay

Over 10317+ Instantly Bookable Vacation Homes in or Near Montego Bay
Storey Lake Dream Villa with Private Pool From US $942
         

9.2 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Magical Townhome private pool in Storey Lake From US $522
         

9.0 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Country Feel,Private Pool,Spa, Game Room From US $220
         

9.6 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Cozy Family 4-Bedroom Bella Vida Home Near Disney World From US $264
         

Luxury Townhouse w/Free Waterpark & Pools 10 Min to Disney From US $214
         

About Montego Bay Vacation Rentals

With more than 74 Montego Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bigpineresortcottages 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 Montego Bay.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bigpineresortcottages Montego Bay, 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 Montego Bay. Places to stay near Montego Bay are 123.41 ft² on average, with prices averaging US $427 a night.

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

Top Rental Accommodation Types in Montego Bay

Type Count
Cottages 67
Resorts 4
Vacation Homes 3

Use these Quick Filters to Find a Vacation Rental in Montego Bay

Pro Tip: Bigpineresortcottages makes it easy to compare the best listings on Bigpineresortcottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bigpineresortcottages 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 Montego Bay.

Weather in Montego Bay

View the weather forecast for Montego Bay before booking your Montego Bay 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

Complexes around Montego Bay, FL


Montego Bay Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Montego Bay?
How many vacation rentals are available in Montego Bay?

Currently, the total number of properties listed in 2026 is over 74 in the Montego Bay area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Montego Bay.