Montgomery Cottages - Vacation Rentals in Santiago

Peyton's Patio Homes in The Villages, Florida From US $202
         

10.0 (13 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Sand Hill Crane Cottage From US $144
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Resort Access: Pet-friendly Home in The Villages! From US $375
         

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10.0 (4 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Great location between Sumter Landing/Spanish Springs. Golf cart included From US $96
         

2/2 Biscayne Model w/Golfcart From US $203
         

10.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
1/1 Villa in The Village of De La Vista From US $190
         

8.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Santiago

Over 825+ Luxury Places to Stay in or Near Santiago
Paradise on the Preserve w/hot tub and golf cart From US $554
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Landing Incredible 1BD Pool Clubhouse From US $486
         

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New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
-Villages Luxury Living~Pool & Golf Cart- From US $420
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Pool

Top-Rated Vacation Rentals with a Pool in Santiago

Over 587+ Top-Rated Vacation Rentals with a Pool in or Near Santiago
Entire 3 Bedroom Home in The Villages - Sleeps 10 From US $287
         

10.0 (129 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hot Tub House - Entire 3 Bedroom House in The Villages From US $277
         

VILLA 2 MASTER SUITES & 2 GOLF CARTS From US $140
         

10.0 (79 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Marilyn’s Romantic Getaway From US $114
         

10.0 (67 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Santiago

Over 278+ Pet-Friendly Vacation Rentals in or Near Santiago
Private Lanai and Patio The Villages Resort Home! From US $226
         

Private Lanai + Patio: The Villages Resort Home! From US $179
         

9.2 (59 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Santiago on PetFriendly.io

Large Vacation Homes & Villas in Santiago

Over 136+ Large Vacation Homes & Villas in or Near Santiago
Spectacular water and golf course views From US $195
         

10.0 (9 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Pool & Golf Cart! Villa By Spanish Springs From US $255
         

Wheelchair Accessible Vacation Homes in Santiago

Over 18+ Wheelchair Accessible Vacation Homes in or Near Santiago
Lovely Lady Lake Home w/Resort Amenities & Lanai! From US $163
         

Holiday Inn Express Hotel & Suites - The Villages by IHG From US $124
         

9.0 (141 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Waterfront Inn From US $155
         

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9.2 (1322 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
TownePlace Suites The Villages From US $111
         

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8.6 (272 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Hampton Inn & Suites Lady Lake/The Villages From US $122
         

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9.0 (1008 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
3 Bedroom Designer Home Glenbrook The Villages From US $134
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Quiet Villa in The Villages near Savannah Center and Glenview Golf Course From US $130
         

Santiago Vacation Rentals and Airbnb Places to Stay Under $200

Over 552+ Santiago Vacation Rentals and Airbnb Places to Stay Under $200
Village Of Country Club Hills COUPLES ONLY From US $65
         

9.1 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Lanai & Golf Cart: The Villages Vacation Rental! From US $122
         

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

Instantly Bookable Vacation Homes in Santiago

Over 455+ Instantly Bookable Vacation Homes in or Near Santiago
Cozy Villages villa, 2 bed, 2 bath. Great Location From US $107
         

10.0 (49 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pool, Golf Course View Home, 4 place golf cart From US $228
         

Pool, golf cart, private Paradise! From US $339
         

10.0 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

About Santiago Vacation Rentals

With more than 24 Santiago vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages 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 Santiago.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Santiago, 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 Santiago. Places to stay near Santiago are 701.66 ft² on average, with prices averaging $184 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Santiago 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 Santiago

Type Count
Cottages 21
Vacation Homes 3

Use these Quick Filters to Find a Vacation Rental in Santiago

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

Weather in Santiago

View the weather forecast for Santiago before booking your Santiago 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

Santiago Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Santiago?
How many vacation rentals are available in Santiago?

Currently, the total number of properties listed in 2026 is over 24 in the Santiago area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Santiago.