The Villa streets are filled with evidence of the previous teams. Graffiti suggests they turned on each other, even when their lives were at stake.”— Loading screen
The Sierra Madre Villa was the private city of the guests, employees and workers of Frederick Sinclair, situated just before the casino. The streets were built so that cars can not circulate, preventing pollution and noise nuisance. 
In addition to the main area, the Villa was composed of four districts:
- Medical District, containing the Villa Clinic.
- Puesta del Sol, which had numerous clashes and arguments with the casino construction crews and the construction lagged behind Salida del Sol. It was as if construction efforts ran out of steam and money.
- Residential District, for the casino's high rollers and entertainers.
- Salida del Sol, the home of the church and many of the casino staff.
To avoid having to spend too much money for the construction of the villa at the expense of the casino, it was poorly constructed. The material used for the Villa's construction was "sand barely held together with spit and glue." Buildings and structures in the Villa were completely unstable and could collapse overnight. All of this caused construction crews to suffer numerous setbacks and accidents. To prevent this discovery on the part of employees of the Sierra Madre, senior persons destroyed all medical reports, and were also protected legally. In addition, shipping problems also plagued the Villa. Construction explosives, countless crates of steak knives, and more were shipped to the Villa, paid for, and left.
In the center of the Villa is a fountain with a holographic projector that projects a hologram of Vera Keyes when Elijah is not speaking to the Courier. The Villa is then split into two sides, east and west. Both sides are equally confusing and maze-like.
Heading east from the fountain, there is a Sierra Madre vending machine on the right of the entrance. After a short while, the path forks; the alley on the left leads to an open area surrounded by apartments which has a gift shop to the right. A hologram vendor is still functioning inside. Upstairs from the shop are two doors; the first leads to a Cloud-filled courtyard, but looking off into the distance through the door the white hand print of a Dean's secret stash can be seen, accessible by nipping across the balcony on the upper level. Through the other door of the shop is a balcony which connects to a room with a bed (which is unusable) and an electric hot plate. Through the door is a broken banister that drops down to the point where the path split.
Continuing down the street, the path turns after hitting a fountain. There is a room on the right with some supplies and a first aid kit. Continuing east on the path brings one to the the entrance to the Residential District on the right, followed by a straight passage. Following the passage, the path splits again; to the left is a courtyard filled with the Cloud. There is a door in the far back (to the right of the entrance) that is free of the Cloud. The room exits to an alley leading to an open area with a couple radroaches and a gift shop (which holds nothing notable).
Continuing straight, avoiding the split, there is a small courtyard with another Sierra Madre vending machine further on the right. In the far south of the extension is a locked gate (hard) leading toward a gift shop above the gate after a room with mechanical components and a workbench. The street along the gate leads straight to the entrance of Salida del Sol. South from the vicinity of the Salida del Sol entrance is a corridor leading to a dead end with a ghost person seemingly guarding a supply cache. Another of Dean's secret stashes is in the store on the left.
The street leading west of the fountain leads directly to the entrance of the Medical District with a Sierra Madre vending machine shortly afterward. The street leads to a courtyard that splits. To the northwest is the entrance to Puesta del Sol on the left and a hallway that leads to an open area filled with the Cloud. The area has a hallway leading to some ammunition boxes and a first aid kit is found in the open area along the wall.
In the south of the split is a stairway leading up to a clearing with a skeleton stabbed by a knife spear. Next to it is a small fountain and another stairway up that leads to a clearing with a fountain and a nearby terminal. The terminal turns on a hologram atop the fountain. An archway to the west of the fountain takes one downstairs to an area with radroaches. Following the radroaches is an amassed collection of the Cloud which has a safe room near the entrance of the Cloud, but is trapped with a grenade bouquet. The Cloud filled hallway leads to another courtyard with the Villa Police Station in the south-southwest.
Going upstairs (to the north) from the fountain with the hologram leads to a straight path to the courtyard containing the police station. Halfway through the corridor is a door of a room filled with the Cloud. Upstairs, there are several wooden planks extending to a broken balcony with ammunition, grenade boxes, and a first aid kit at the end.
Just to the north of the back (Very Easy) locked entrance to the Police Station is a courtyard; upstairs in the west apartment off the courtyard is a set of Sierra Madre armor on the bookshelf next to it.
- Three of Dean's Secret Stashes. First on the way to the police station, near a firehose box and behind some columns. Second inside a shop near the Salida del Sol entrance. Third in a cloud-filled second-story area reached from the hologram vendor in the East Villa.
- Over 500 Sierra Madre chips, scattered all over the villa.
- Pugilism Illustrated can be found on the ground on the opposite side of the fountain from which Dead Money starts.
- Acoustic guitar on the second floor of the building at the top of the stairs directly across from the police station.
- Vending machine code - "Return outfit item" can be found in a cash register sitting inside the broken cooler in front of the hologram vendor. The hologram vendor can be found North of the Residential Area entrance.
- There are three Lover's Mark stashes; two near the Salida del Sol entrance and the other slightly east of the Villa Police Station. All are marked with pierced heart graffiti.
- 10 of Hearts - Sierra Madre: Some distance north of the Villa Police Station and west of the room containing the 5 of Hearts, on the interior corner of a walkway to the southeast of a wall fountain.
- 5 of Hearts - Sierra Madre: Some distance east of the 10 of Hearts and northwest of the hologram which can be turned on with a nearby terminal, in a second floor room above one containing a tripwire and swinging girder trap, under the south end of a couch against the east wall.
- Ace of Spades - Sierra Madre: In the southern part of the fountain where you first wake up and gather your team.
- Joker 2 - Sierra Madre: Inside a second floor room above a gift shop some distance north of the doors to Salida del Sol South and southeast of a wall fountain, partially covered by a bed in the northwest corner.
- 4 of Spades - Sierra Madre Inside a room on a courtyard north of Salida del Sol entrance.
- Find Collar 8: "Dog"
- Find Collar 12: Christine
- Find Collar 14: Dean Domino
- Sierra Madre Grand Opening!
- ↑ No More Parking Tickets: Sinclair's laid out the streets so narrow, cars can't even come into the Villa. Resources being what they are, he may not want folks to waste gas coming here. Cuts down on traffic noise, too.
- ↑ Puesta del Sol South terminal - Personal log: Asked the Foreman how come no one's wised up yet, and he just winked, said we got someone watching out for us, an ace in the hole. As long as we're good until showtime, this whole Villa's going to be the biggest con of all time. That's because half the maintenance shipments aren't coming through - Sinclair's too blinded by that Starlet to see beyond the casino, so we're able to cut corners when we need to, and no one's going to look too close at the budgets while the casino's big opening is underway, and after that, we'll be long gone.